It's not that I mind having more friends, but...
March 27, 2015 12:57 PM   Subscribe

It seems that whenever I meet a woman I really like and think I have a connection with, she can only view me as a friend. I'm generally okay with this, because their great qualities as people is what attracted me to them in the first place, and those don't change just because she's not interested in me. But when it happens over and over and over again, it does make me wonder whether there's something I'm doing wrong. Why is it I'm consistently viewed as good friend material, but not good lover material?

The most recent instance happened just a few weeks ago. I (32) met someone (28) around December in a volunteer activity I'm very involved in, and we had an instant rapport. I thought she was intelligent, principled and funny, and had an energy and enthusiasm towards things that just couldn't help but draw me towards her. Also she knew how to make an amazing eggplant curry, I was blown away by how good it was! We had a lot in common in terms of interests and values and communication styles too. I thought she was interested in me (we'd cuddled while watching movies a few times) and so as she was leaving one night, I asked whether I could kiss her. She got flustered and said we'd need to talk later.

One week later she told me that she could only see me as a friend, and that when she realized I was interested in her she had hoped I would have gotten her signals, but apparently I needed to be told directly. She said she really liked me as a friend and still wanted to hang out with me, and I said I wanted that too, but that I would need some space to process things, which is what I've been doing for the past few weeks.

While I'm very sad things didn't work out the way I wanted them to, what's been bothering me lately isn't so much this individual instance but, rather, how it's the latest iteration of a pattern that has repeated itself literally since puberty, and I'm 32 god damn years old now. Time and time again, women like me as a friend but can't see me in a romantic context. They've told me I'm funny, they've told me I'm intelligent, they've told me I'm kind and compassionate and empathetic, they've told me they feel comfortable being open around me, they've told me I'm not a bad looking guy and that there's nothing wrong with the way I look. And I believe they're being honest. But they just can't see me as anything more than a friend.

And this isn't necessarily a bad thing-- I like that they think all these positive things about me, and while it's a little disappointing, it's not like I haven't appreciated their friendship over the years. Some of these women have, indeed, become some of my closest friends and I wouldn't trade that for a transient roll in the hay with them.

But this is only if you take each case individually. When considering these cases as a pattern, I feel bewildered, hurt, frustrated, depressed and--at this point--utterly defeated. When something happens once, it could be a fluke. When it happens three times, it's a NYT trend article. When it's happened dozens upon dozens of times, though, it makes me think there is something deeply and fundamentally broken about me. My friends try to cheer me up, and say I just need to wait for the right person, but frankly I'm getting sick of people telling me there's nothing wrong with me when there very clearly *is* something wrong with me or else I wouldn't be in this situation.

It's obvious the problem isn't interacting with women in general--I'm guessing about 85-90 percent of my friends are women. And I've had relationships in the past, but they've generally been very few and far between (my last one was in 2010, and the one before that was 2005) and they last, on average, about six months. Whenever I have dated anyone, it's always moved very fast, and we're usually exclusive within 6-8 weeks. While I've had short flings too, they're also very infrequent and they never go anywhere either.

I do feel like I've come a long way since when I was younger in how I view women and relationships. I'm not sizing up every women I meet as a potential relationship, I've got an active an independent life in terms of hobbies and friends (I'm very involved in radical left activism in my city, and have several accomplishments there I'm proud of), and I'm far more aware of what kind of person I'm looking to be with and what sort of relationship I'd like to have. But I'm lonely. And horny. But mostly lonely. Well, okay, about 50-50 of both.

I feel like, considering how often this happens, it's unlikely that it's been a different thing every single time. There has to be some common thread, something about me, some quality I have, something I'm doing, that leads me to be highly valued as a friend but not at all as a potential romantic partner. What's particularly concerning is I feel like this makes it more difficult for me to be discerning in what kinds of relationships I do enter when I have the chance because I think “if I turn her down, who knows how long it will be before someone else comes along?” This has led me into making some unfortunate choices over the past few years when it comes to the aforementioned short flings.

I don't know what to do about this situation. It's become a major contributing factor to my depression (yes, I am in therapy and on medication) and has played a number on my self-esteem. I feel like every rejection is due to me not being good enough, and even though intellectually I know that's bunk, I retain this visceral feeling that the reason I am where I am is because I'm just an inherently low-quality human being. I'm starting to think this is permanent, that my life is indicative of some sort of sexual Calvinism, and I'm just not one of the Elect, and there's nothing I can do about it. I know this is the last thing you should be feeling if you want women to desire you but I can't shake this feeling, as irrational as I know it is, as I think the empirical evidence supports it.

Narrowing this all down to specific questions: What could I be doing wrong? What features could make someone desirable as a friend but not as a lover? Do the qualities that make for a good friend stand in opposition to the qualities that make for a good lover? How do I untangle this ouroboros of suck where the more I hate myself the more romantically untouchable I become and the more romantically untouchable I become the more I hate myself? What should I do to address this problem? And finally, if this is indeed my life, how do I make peace with the fact that I will die alone?
posted by KantGoOn to Human Relations (84 answers total) 13 users marked this as a favorite
I think it mostly goes this way for everybody. Making friends is a great way to meet potential romantic partners. But only a relatively small percentage of the people who make good friends are also attractive to you as romantic partners, so it shouldn't be a huge surprise when the desire to move in that direction isn't mutual. So, in that sense, I wouldn't get too focused on the idea that you're doing anything wrong. Though maybe you do need to get better at reading signals to avoid as many of the really awkward situations as possible.

If this is really affecting your mental health, why don't you just give up on trying this approach to dating. We live in a world where internet dating is huge, safe, successful, and mainstream. When you go on a date with someone you met on a dating site, all the cards are on the table about whether the relationship is romantic or not.

I would prescribe going on a whole bunch of internet dates, getting used to figuring out whether they're going well or not and reading all the other sorts of signals people send in these situations.
posted by 256 at 1:09 PM on March 27, 2015 [6 favorites]

Do the qualities that make for a good friend stand in opposition to the qualities that make for a good lover?

Not at all. But sexual attraction is the key criterium separating the former from the latter. You may just be approaching women who are your physical type in terms of attraction but for whom you are not their physical type. If you're confident that you're taking appropriate steps with your self-care in terms of hygiene and styling, you may want to give internet dating a try so that you can better target your search for a romantic partner and start off on the right foot with someone you know finds you attractive.
posted by northernish at 1:14 PM on March 27, 2015 [12 favorites]

Are you waiting a long time to make your move? I ( and I imagine others) have a time window that I would expect a guy interested in me to make it plain. When that window has passed I think he's not interested and just think he only wants to be friends. Then the way I view him and the relationship completely changes to platonic and it almost never changes back to romantic. You may need to speed up your idea of when its appropriate to go for that kiss.
posted by Requiax at 1:14 PM on March 27, 2015 [29 favorites]

Are you meeting people specifically for dating? Try going on OKCupid or Match, rather than attempting to date women you're meeting in non-dating situations. And I also think that you might want to switch up your approach: try going on dates, rather than dating. Try going on dates with different people and see if you have chemistry with one or more of them. If you actively date people, you might have more luck.

And if you do find yourself attracted to a woman who is a friend, talk to her first rather than asking if you can kiss her. Say something like, "What do you think about going on a proper date? I'd like to date you." and see what she says. Kissing or asking to kiss takes it to a physical place, escalating intimacy in a way that some people might find uncomfortable without prior discussion.

if this is indeed my life, how do I make peace with the fact that I will die alone?
You learn to be your own best friend. I might die alone, too - but I'd rather die alone than be stuck in a dead-end relationship with someone who isn't right for me for the rest of my life. Let's be brutally honest, here: You could get married and have a wonderful spouse and they could die 20 years before you do. So even if you do find someone to share your life with, that might not even last. And that has to be OK.

I personally find that hobbies are really helpful for me - specifically, hobbies where I create things.

Sometimes you just cry and feel bad for yourself. Not for too long, but yeah, sometimes I get in a little ball and just cry and feel sorry for myself. I've had a chronic illness my whole life, I'm not particularly good-looking, I can't have children, and I'm probably going to die alone. It sucks and it's ok to feel bad about it sometimes. Not too often! But sometimes. And then I get up and I take a hot shower and I get creating again, because that is both a distraction and helps me feel worthwhile. I am also 32 goddamn years old and I'll tell you, it is kind of crushing to look around and see that literally every one of my friends that is relatively sane and my age is, in fact, married and has been for years now. It's OK to feel bad about the cards I was dealt: they're not the best! But I really like myself and that's enough for me. It has to be enough.

Oh, also: get a pet, if it's possible. The overflow of unconditional love that I get from my cat helps a lot.
posted by sockermom at 1:16 PM on March 27, 2015 [18 favorites]

Aw, I feel for you. This sounds really frustrating. A couple of ideas, from someone who has never seen or met you:

The first thing that comes to mind is, are all of these women significantly more attractive than you are? Even if you're average, if you're repeatedly pursuing people who are more conventionally attractive than you, that may be a contributing factor.

The only more personal thing I can come up with is: Are you ... I don't know how else to say this...annoying about your activism? Like, possibly in a way that is endearing but kind of a ladyboner-killer? This may have nothing to do with you! It's a tendency that seems to be I guess a thing sometimes among politically very active people, especially if they see everything through a particular lens, and maybe are a little socially immature.

Additionally, maybe there is A Thing that nobody wants to mention (halitosis, maybe you're kind of effeminate, gross teeth?) that is standing in your way. If so, I hope someone will tell you, and kindly. Maybe you can get one of your friends to level with you on this by saying "if there were a particular problem that I needed to solve, like bad breath or gross teeth, I hope you'd help me by letting me know, friend to friend."

Best of luck to you.
posted by chesty_a_arthur at 1:17 PM on March 27, 2015 [32 favorites]

People are weird. Relationships are weird. Seriously, there isn't any rationality to it all, and you can't interpret rejections as rational decisions that make statements about your self-worth, "relationship value," or some bullshit like that, because they just aren't. That way lies madness, or dragons, or whatever. Anyway, you're putting yourself out there, you're meeting people, and you've gotten into relationships in the past, so you're doing something right. There's nothing wrong or broken about you — I think for everyone it's just fundamentally a grind: you keep failing over and over again until something sticks. I guess it's easier for a very small minority, but there's nothing intrinsically right about them or their "value" because such a thing doesn't exist. They just got lucky, and a huge component of that is putting yourself out there and being open to failure. That's honestly all there is to it.
posted by un petit cadeau at 1:18 PM on March 27, 2015

I thought she was interested in me (we'd cuddled while watching movies a few times) and so as she was leaving one night, I asked whether I could kiss her.

I have trouble believing the the "cuddled while watching movies a few times" stage happened before the "I have accepted that I am attracted to her" stage. You said you're not sizing up everyone woman you meet as a potential date, and, hey, that's great, but clearly at some point in your relationship with this woman you said to yourself "this would be a person I want to kiss" and you verbalized that way too late for your own emotional wellbeing.

Don't get into this situation, which I'm going to assume you've been in more than once, with women to whom you are attracted anymore. You're putting yourself into some liminal erotic/platonic space, and when the line is drawn by the other person, you're heartbroken, and it sucks. I know plenty of people can do the slow-burn friendship that slowly progresses into a relationship thing but not everyone can, and not everyone who wants to can.

I think you need to put yourself into much, much more blatant "this is a date" spaces with women you find yourself attracted to or develop genuine attraction when you're already in that context (e.g. internet dating, set-ups from friends, etc.)
posted by a manly man person who is male and masculine at 1:25 PM on March 27, 2015 [9 favorites]

I think women do better when you communicate from the beginning your sexual interest in them. Eye contact, smiling, compliments, light touching, jokes. If they reciprocate, you're in great shape. If not, bail.
posted by Ironmouth at 1:28 PM on March 27, 2015 [12 favorites]

I'll try not to threadsit, but since this has come up a lot already, I have indeed been Internet dating for years. I send messages about 3-5 sentences in length, draw from something in their profile, and I end with a question. During periods I go on dating sites, I'll send about 30 messages a week. It usually results in about two or three dates that never advance past the third date before either me or the other person thinks it's not working.

I generally am not waiting a long time to make my move: usually about a month and a half or so of getting to know the person, and I have been making it a point to make my interest clear and explicit (through words) rather than beat around the bush like I did in college.

I now pursue people pretty exclusively within radical left circles, so we're all pretty politically active, though this had not always been the case before I began refining what it was I was looking for, but the issues have been the same in and out of this culture.

Finally, I have indeed been asking my friends to be straight with me even at the cost of saying something hurtful. Recent responses have included: I'm more cute like a teddy bear than cute like a potential lover, I need to focus more on being in the present moment instead of always comparing things to the past or future, I put a lot of focus on being entertaining which makes it tough to be vulnerable and authentic, I can be overly accommodating, and, finally, a shrug and "I don't know, there just wasn't any chemistry."
posted by KantGoOn at 1:29 PM on March 27, 2015 [4 favorites]

When I read the initial part of your question, my reaction was to assume that you're in the habit of sizing up many of the women you meet as potential relationships. So maybe there's still a little work to do there. I know! It's really hard. I have had that problem, too.

Have you ever known people who you thought were really really really great! And they were single and didn't want to be, but you didn't want to date them? So you keep them as friends. That has happened to me fairly often. They inevitably find someone who is great for them, and my reaction is usually one of being so glad that they have found someone that is such a good fit for them! I think you're that person.

So my advice would be to stop worrying. Just keep doing what you're doing. Relax. Be ok with being single, because that's what you are right now, and it's good to accept the way things are. Work on not being lonely by exploring those friendships outside the context (or hope) of romance. Make BFFs with yourself.

As they say: "Stay open to possibilities, what you seek will come when you least expect it."
posted by aniola at 1:31 PM on March 27, 2015 [2 favorites]

I’m going to build on something chesty_a_arthur mentioned above.

Some years ago, I worked with a guy. He was a great guy. Tall, well built, nice looking, friendly, funny, smart. All in all, a great catch. And he also had horrible breath. Made-you-want-to-recoil kind of breath. I have no idea how he was so unaware of it, because he went around blowing his breath everywhere like nobody’s business. Everybody talked about his breath. But no one talked to HIM about it. He was well liked at work. The women found him attractive. But not a single one of them could ever imagine kissing him.

I’m not saying you have this problem. But you could have a similar problem of which you are unaware. Is there anyone you can really trust to be honest with you? Ask the questions straight out: do I have bad breath? Do I have body odour? Do I have dandruff flakes? Etc. Ask in a way that lets them know it’s 100% ok for them to be honest. And, good luck. I feel for you! This sounds very frustating.
posted by yawper at 1:36 PM on March 27, 2015 [7 favorites]

I need to focus more on being in the present moment instead of always comparing things to the past or future, I put a lot of focus on being entertaining which makes it tough to be vulnerable and authentic, I can be overly accommodating

Are you addressing these things?

Have you asked these close friends if they know any nice single ladies you'd be compatible with who are looking to develop a romantic relationship with someone?
posted by feckless fecal fear mongering at 1:37 PM on March 27, 2015 [4 favorites]

I generally am not waiting a long time to make my move: usually about a month and a half or so of getting to know the person...

This is the opinion of one person on the internet, but a month and a half is an incredibly long time. Expressing your attraction to a person a solid month and a half into an apparently intimate friendship will definitely get the confused and flustered response you got in the situation you described as she attempts to square what the hell just happened.
posted by a manly man person who is male and masculine at 1:38 PM on March 27, 2015 [99 favorites]

I agree with everyone who says that while a certain degree of this is completely natural, if it's as much of a pattern as you suggest, you're probably pursuing women who aren't physically attracted to you.

In fact, the anecdote you describe 100% supports this explanation. Most people, I think, sort through this within the first few minutes of meeting someone - they figure out whether or not they're attracted to someone, and whether or not that person might be attracted to them. That's why speed dating kinda works: all of our innate qualities as human beings aside, usually a first impression is enough to give a basic yes/no/maybe, and - this is key - to figure out how the other person categorizes you. The truth is that most actual dating takes place in the 'maybe' zone, because yes/no mis-matches are more common than not: the creepy super in my building would definitely YES me, and I would definitely YES Chris Hemsworth, but neither of those relationships are gonna happen, you know?

It sounds to me that you're going after your yes's without giving much thought to whether they're yes'ing you. The woman you dated said she felt like she was giving you signals you didn't pick up on -that is really key. If you want to interrupt this cycle, you need to start reading these hints and body language signals better, so that you move on after fifteen minutes instead of spending months pursuing something that isn't going to happen.

You sound like you've turned into a pretty cool guy, but I do think that one thing that may be hanging around a bit from your Good Guy TM days is a mindset that a woman's attraction can be earned as a reward for good behavior. Charm can turn a hesitant maybe into an enthusiastic yes, but if someone isn't at least a little bit attracted you, no amount of charm is going to change that. It's no reflection on you personally -there are people out of everyone's league, and there are probably people who are crazy about you that you wouldn't look at twice.
posted by pretentious illiterate at 1:38 PM on March 27, 2015 [23 favorites]

I generally am not waiting a long time to make my move: usually about a month and a half or so of getting to know the person, and I have been making it a point to make my interest clear and explicit (through words) rather than beat around the bush like I did in college.

I think a month and a half is an absurdly long time to make a move in adult dating, and I suspect I'm not alone.
posted by ktkt at 1:39 PM on March 27, 2015 [43 favorites]

I'm going to go out on a limb and guess that you're not being flirtatious or indicating to women that you find them sexually desirable.

You're doing something again and again that indicates to women that you want to be friends only. From the way you phrased your question, you mention everything you found attractive about this most recent woman but you never mention if you thought she was sexy or anything about your chemistry. It may be that you're projecting the same non-sexual aura with women you meet.

Do you flirt or exhibit non-platonic behavior? It may be that you're coming off strong with the emotional closeness, but if you do that without also indicating that you want to touch a person and find them sexually attractive, women will put you in the friend category.

Up your flirting game early on. You were hanging out with this woman a bit but only cuddling, right? That's not very sexy and you should be a little more aggressive and show you're attracted physically. You should be going in for a kiss right around the same time you're cuddling on the couch.

If you're not showing that you find someone sexually attractive and you're not being flirtatious and joking/teasing, you're going to mentally compartmentalized as a friend.
posted by kinetic at 1:39 PM on March 27, 2015 [8 favorites]

I think you sound like you're the classic "too nice" guy with no edge, no danger, no challenge for the women you're pursuing. I bet you are pursuing women who have much better options than you, from an aesthetic point of view. All this harping on left activism may be offputting too.

you need to be more deliberate and crafty, more edgy and flirty, not just a cheerful all-cards-on-the-table guy like I suspect you are.
posted by jayder at 1:44 PM on March 27, 2015 [12 favorites]

I generally am not waiting a long time to make my move: usually about a month and a half or so of getting to know the person, and I have been making it a point to make my interest clear and explicit (through words) rather than beat around the bush like I did in college.

This is WAYYYYY too long. And make your interest known with your eyes and your body, not words. You gotta up your flirting game, son.
posted by kinetic at 1:46 PM on March 27, 2015 [28 favorites]

These kinds of questions are hard, because I think a large part of the answer is so dependent on actually seeing you in person and interacting with you, to see if any things pop up. We can only give generic advice. Your friends can't really give you good advice, because they love you and are around you all of the time, so are probably blind to any faults (this is a good thing, and why they're your friends).

I think you need in-person, unbiased answers. The only ways I can think of getting this are hiring a woman dating coach (or probably multiple, to get many views), and/or asking for help from women friends of friends who don't know you.

I have lots of anecdotes of why it didn't work out for friends of mine that tried to ask me out, but it always boiled down to not feeling attraction - and I don't mean due to their physical appearance - I mean behavior traits. Too clingy or too dependent or too available or not being sure of themselves or sending off weird vibes, etc. Hard things to diagnose over the internet, relatively easier in person. Best of luck, you sound like a great person - you just need to up your fishing techniques.
posted by umwhat at 1:50 PM on March 27, 2015 [2 favorites]

I generally am not waiting a long time to make my move: usually about a month and a half or so of getting to know the person

I am more in the a minute and a half timeframe for making my sexual interest clear. Get bold. People like that.
posted by Ironmouth at 1:50 PM on March 27, 2015 [27 favorites]

Make a move sooner. I mean, if you're making plans with someone you're attracted to, make it clear if it's a date or if it's just friends. There's an art to this. You want to lead confidently but also be interesting and non-threatening. If you're getting a lot of asexual movie dates, you're probably attractive but TOTALLY PASSIVE as far as expressing romantic interest. Try saying clearly what you want, ideally in a fun and interesting way, then listen to what she says.

i.e. not "Would it be alright if I kiss you" after she's been using you for cuddling when you want something else.

More like, if it's gotten that far and you haven't done anything, "I've got a problem. When you put your arm around me on the sofa it makes me realize that I'm really looking for a relationship right now." Then, wait for her to reply.

1.5 months is a long time. Try asking people out after talking to them for 10 minutes. Honestly you'll have a pretty good idea after 30 seconds if you want to date them or not. You're not agreeing to marry them, you just want to make sure you're both possibly interested in a relationship before investing a bunch of time in a friendship that's not really a friendship.

Also, if you haven't kissed them, don't fixate on them, and do keep seeking out other women to date.

"Just friends" non-dates are depressing -- AVOID these! Specifically, if you're not having sex, don't watch more than one movie 1-on-1 with them, and never go shopping with them.

Try not being accommodating -- think "win-win" or "no-deal". You won't find what you want by settling for what you don't want.
posted by sninctown at 1:51 PM on March 27, 2015 [2 favorites]

Finally, I have indeed been asking my friends to be straight with me even at the cost of saying something hurtful. Recent responses have included: I'm more cute like a teddy bear than cute like a potential lover, I need to focus more on being in the present moment instead of always comparing things to the past or future, I put a lot of focus on being entertaining which makes it tough to be vulnerable and authentic, I can be overly accommodating, and, finally, a shrug and "I don't know, there just wasn't any chemistry."

This, to me, is a picture of someone who isn't entirely at ease with or in himself. Self-acceptance is attractive; it also often allows others to feel at ease in your company. It's a precondition for authentic communication. It sounds like your general orientation is to anticipate, appease, or accommodate others. Is social anxiety part of the picture? Is self-assertion something you're working on in therapy?

I think taking up a physical practice, like martial arts (or really any sport or focused physical activity) could help you a lot, in a number of direct and indirect ways. Physical confidence can translate to confidence in lot of other areas (as well as self-acceptance).
posted by cotton dress sock at 1:53 PM on March 27, 2015 [8 favorites]

It sounds like you just don't have enough... swagger? I want to know that a guy wants me for my mind AND my body. Flirting, subtle innuendo, appropriate touching, telling me I'm beautiful--that shit works. It doesn't work if I think you are a douchey neanderthal though--that's where the common interests and platonic fun-times come into play. But relationship material has to have both, and it needs to start happening pretty soon. Speaking for myself, as soon as a guy is in the friend-zone, there's not much he can do to get out of it. So yeah, pick up your game. It's my opinion that it's easier to go from possibly-sexy-zone to friend-zone with a guy than the other way around. Y[other women's]MMV. There's nothing wrong with showing a woman you are interested--it's only a problem if she has shown she doesn't reciprocate and you continue to pursue it.

But yes, I think you are probably too much of a nice guy and need to be more of a guy who show's he's interested. It sucks, but it's a delicate balance that the majority of people never master.

Good luck!
posted by greta simone at 1:53 PM on March 27, 2015 [3 favorites]

I think you sound like you're the classic "too nice" guy

Hmm. I don't buy into the idea that "nice guys" aren't valued as relationship material, or that most women are looking for more of a challenge. But it's true that it sounds like you're not flirting enough. How confident are you? For me, this plays a major role in attractiveness. Teddy bear cuteness can definitely be hot paired with the right personality. But if you're willing to briefly share a picture, we might be able to say more.
posted by three_red_balloons at 1:54 PM on March 27, 2015 [1 favorite]

If you think she is cute, ask her on a date right then. Don't infiltrate your way in as a platonic friend and then spring the "by the way, I think you're cute!" on her six weeks later. The way you are doing things now isn't fair for you or for them.
posted by Dip Flash at 1:55 PM on March 27, 2015 [29 favorites]

It seems like you are spending a month and a half deciding that you'd like her to be your girlfriend. That's ok. You still get to spend as much time as you need on that decision.

During that time, you should be kissing and making out and, after a few dates, sleeping with her. That's part of getting to know her as a potential girlfriend.
posted by amaire at 1:56 PM on March 27, 2015 [11 favorites]

I'm going to go out on a limb and guess that you're not being flirtatious or indicating to women that you find them sexually desirable.

This seems reasonable, but - as you know in activist circles - for the lord's sake, don't "go for the kiss" without explicit consent. I mean, you obviously know that, but it's an important thing for people giving advice to know - there are sweeping "romantic gestures" and "indications of interest" that are going to creep people the fuck out in activist settings.

And indeed, a month or before asking someone out isn't especially long in activist time - these are all people you see once every week or two at meetings and events, right? I would say that it's certainly okay to ask people out sooner, but it's not something that people in my activist circles do that often.

Finally, I have indeed been asking my friends to be straight with me even at the cost of saying something hurtful. Recent responses have included: I'm more cute like a teddy bear than cute like a potential lover, I need to focus more on being in the present moment instead of always comparing things to the past or future, I put a lot of focus on being entertaining which makes it tough to be vulnerable and authentic, I can be overly accommodating, and, finally, a shrug and "I don't know, there just wasn't any chemistry."

This all sounds like extremely unhelpful advice because it's super subjective. It sounds to me either like they aren't telling you something or like you need to follow up to get specific examples.

By "cute like a teddy bear", do they mean that you're chubby? Or tiny and adorable? I think that in either situation, you probably need a bit more gravitas - I would suggest putting yourself in leadership situations more often, situations where you need to make decisions, run meetings, push people to do stuff. Like, I have a lot more gravitas now than when I started [doing gravitas-generating thing].

Also, if you're chubby you'll need to up your clothing game and maybe put a little money into it, especially in terms of well-fitting and slightly structured clothes.

How is your haircut? Is it floppy and moppy? If you are a gentle, amiable, funny person with floppy hair, you may read as younger and more little-brother-like.

Basically, when I'm visualizing you, I'm visualizing some of my friends from the Occupy milieu - kind of loose-limbed, seem younger than their years, never bother with haircuts or glasses, lots of enthusiasm for niche activist stuff like internet security (but not jerks about it), "comfortable" puffy black athletic shoes, loose clothes in random colors. I know a guy - and he's a fantastic guy but probably not you, and I would go out with him in a minute if asked if I weren't, like, ten years older even though I generally don't date men - who is Very Handsome, very educated, compassionate, funny, tall, and has terrible trouble dating. And I think it's because he is just sort of floppy in affect and exacerbates this with his clothing choices. The thing is, he really is a total catch, but I can see how he needs to show himself to a bit more advantage.

Also - and this isn't as weirdly self-interested as it sounds - do you consider women who are moderately older than you? I feel like when I meet dudes - and I am basically not interested in dating dudes - I can tell that some of the ones I would have totally overlooked when I was in my mid-late twenties/early thirties were actually shining gems, but I was still developing my own discernment and didn't realize this. My point being, it might be that someone who was five years older than you (which can be difficult in radical circles, since they skew young) might be a better bet?
posted by Frowner at 1:57 PM on March 27, 2015 [16 favorites]

It's really difficult to convert friends into something more, unless the feeling is mutual. Waiting until you know them, over the period of 1.5 months, sets expectations as to how you're going to interact. Once this has been set, attempting to change tacks can lead to confusion. This can be especially true if the way in which you're interacting is friendly, such that you open up to each other intimately. In a romantic setting, what I choose to share and when I share it is very different than what I share with my friends.

Many have mentioned that you may not be attractive to the opposite, but there's really only one way to tell: within 1 hour of meeting someone that you have good report, ask them to dinner. Or ask one of your many female friends why you're striking out.
posted by teabag at 1:59 PM on March 27, 2015 [1 favorite]

When people friendzone you it's because they're not attracted to you. They straight up don't think your sexy. That's all there is to it. People always claim that its what inside that matters, but please, grow up. The real world is not a fairytale. It's fucking cruel and people are shallow as hell. I disagree with people that say dating is complicated or weird. it's actually not at all. If you're fit and look like you take care of yourself you wouldn't have any problems. Women are just as shallow as men, they just are socially trained to dress it up better. It's all crap.

My advice is hit the gym, lose some weight if you need to, lift some weights and get in decent shape. You'll never have a problem again (unless your personality or hygiene is actually terrible - but that doesn't seem to be the case since they want to be friends).

And for godsake, stop overthinking this crap. It's super straightforward, don't tie yourself in knots. Being nerdy and in your head is lame, get out, stop dicking around on your phone and get active and actually do something. Politics don't count, most people will think that's kinda gross and are turned off by it. But, if you're shooting for exclusively that type then whatever. You should keep an open mind and broaden your horizons, you don't know the right person for you. But when you talk to people about politics, don't be obsessive or overly aggressive. Listen and have a conversation, focus on understanding the other person's viewpoint instead of harping on your own. That way people might actually want to talk to you about what you're interested in instead of defending themselves. (not sexy).

And you are not a "low-quality human being," that is complete bull shit. We are all the same essentially. Stop listening to your depression and realize your head is jacked up. If you work out and make progress you'll start feeling like you've earned your worth and might sprout some self esteem. I know it's hard, but it's worth it and you can do it the same as any muscle-head out there. Be the best YOU you can be. The rest will take care of itself.
posted by Craig at 2:00 PM on March 27, 2015 [10 favorites]

Although I totally concur that you should not "cuddle" before sealing the deal about actually going on a date. It's confusing and honestly, I think that it leaves a lot of space for you to be taken advantage of by young women who (much like me in my mid-twenties) who really like semi-romantic attention and are not sure how to manage relationships.
posted by Frowner at 2:01 PM on March 27, 2015 [18 favorites]

Wait, do you mean 1.5 months during which you see them in social settings a few times and then after 1.5 months you ask them out?

Or do you mean 1.5 months during which you hang out one-on-one several times (once a week or more) and after 1.5 months you make a move by asking to kiss them?
posted by amaire at 2:03 PM on March 27, 2015 [1 favorite]

If these people are doing things like cuddling you, and yet don't think you're into them, it might be because they assume you're gay. So I would be like "I am not gay" a lot more frequently

But yeah, up your flirt game
posted by internet fraud detective squad, station number 9 at 2:08 PM on March 27, 2015 [16 favorites]

And (and then I'll stop commenting, but if it's useful, feel free to memail me) no matter what people in your social circle may say about cuddling being this totally neutral thing:

1. If someone wants to cuddle and isn't leading you on, that's a sign that they really do view you as totally safe and only a friend.

2. Otherwise they are leading you on, and it will mess with both your head and the friendship. This may be because they are insecure or awkward, not because they are terrible, but it's not a good thing to do.

It is much better to avoid cuddling with people unless you know for a fact that both of you are on the same page about the relationship, whether friendly or romantic.

What does your therapist say about all this?

I know someone who had a similar trajectory to you and didn't find a good, serious relationship until he was 38, and I know a truly dazzlingly handsome guy who likewise couldn't seem to date successfully until his mid-thirties. It's not just about how you look, or even primarily about how you look.
posted by Frowner at 2:15 PM on March 27, 2015 [7 favorites]

While I am not involved in activist circles, and have not been "friend-zoned" [for lack of a better term] to the extent that you have, you do sound a bit like me. You enjoy interacting with people and you're friendly, but the idea of flirting and reading body language and gauging and acting on sexual interest makes you uncomfortable. It's vague and confusing and you're afraid that if you get it wrong you'll be lumped in with those guys. I get it.

I think you should take one particular, concrete piece of advice from this thread and act on it: make your interest known sooner. A month and a half is a long time to make a move, at least in the circles I travel in. I wouldn't be surprised if a lot of women just put you in the 'friend' box after awhile, and that's a hard box to get out of. If you meet someone, and you are attracted to them, try to act on it sooner - make a move, or at least ask her out on an explictly-defined date. Do this in, like, the first couple of weeks.

All of the other advice people are giving you about being more flirtatious or whatever is well-intentioned, and possibly helpful, but it's not as concrete. If you're like me, you have trouble with flirting, because it is vaguely-defined and scary. So, focus first on the easy-to-define thing: make your intentions clearer, sooner.

Also, it may give you hope to know that, while I went years between relationships and never really learned how to flirt or whatever, I am now happily engaged. Your awkwardness about this is not a sentence to a life alone! (And being alone isn't really so bad - I love my fiancee, but occasionally I miss it.) Hang in there.
posted by breakin' the law at 2:17 PM on March 27, 2015 [4 favorites]

I feel you, especially on fear that you're just missing the boat somewhere. I'm very bad at the flirting game, and I make friends with women much more easily than other men. I don't go on many dates.

I will say that I have found myself in friendships with lingering sexual tension that turned into something more. But, goddamn is it rare. It's not going to work for you often. It won't work for anyone often: if you pursue a friendship, you tend to get one.

Are you going on one-on-one datelike things with someone who is available and you're provisionally interested in? Stop doing that. If you think you might be interested in her, ask her out on a date.
posted by BungaDunga at 2:19 PM on March 27, 2015

I think it's possible the cookie has just sort of crumbled this way. I wouldn't really question that something is wrong with you. Based on your question, you actually do seem like a good guy.

The first thought that came to mind was physical attraction. I'm sure you're a decent-looking man, but are you going after knockouts or normal women? I have known a few guys who were well short of what I would consider "hot," but they always went for women who were 10s and didn't have any interest in women who were on their level. You don't sound that superficial, but is it possible you are consistently seeking women out of your league?

Second, are you letting yourself fall into the friend zone by not making it clear sooner if you're interested? If you are interested, you may want to make it clear a bit sooner. Work on flirting a little more. Not in a creepy way, but just be a little more playful up front, and maybe be more direct in letting the woman know you like-like her.
posted by AppleTurnover at 2:23 PM on March 27, 2015

Could you tell us how many times you typically see people and in what settings in the six weeks between meeting them & asking them out? I think there's a very big difference between seeing someone 2-3 times in group settings over six weeks and asking them out, and spending one-on-one time with someone twice a week for six weeks and then asking them out. The former is a good timeline - you've met them a couple times and may have a sense of their personality. The latter is not going to work for most people - if you've spent hours and hours of one-on-one time with someone as a friend, it can be very difficult to transition to a romantic/sexual relationship.
posted by insectosaurus at 2:23 PM on March 27, 2015 [3 favorites]

if you're interested in someone, you should not know how fantastic their eggplant curry is and their favorite movie watching cuddling positions before you've asked them out on a date. some people can be casual friends, move to hanging out one on one, and then quickly move into a relationship - it doesn't seem like you're one of these people, AND THAT'S OK! but to keep trying this tact will keep getting you the same results. lots of women will say no to direct questions of dating, but you at least won't have spent 6 weeks silently pining away while you wait for the perfect time to ask for the kiss.
posted by nadawi at 2:31 PM on March 27, 2015 [7 favorites]

I think part of this is self-fulfilling prophesy. The more you have these experiences, the less confident you become. The less confident you become, the less attractive you are as a romantic partner. I think you need to do something to break the cycle and regain your confidence, perhaps do something out of the ordinary for you and go to a dive bar and pick someone up. Move far faster than usual, be overt about your interest (the venue should make that acceptable, where it might not be in your usual activist circles). If you have to fake confidence for now, do so. Just get a few notches on your belt with willing partners and you'll probably be more attractive, less needy, and happier.
posted by mysterious_stranger at 2:36 PM on March 27, 2015 [1 favorite]

I'll second the suggestion to find a physical activity, preferably something regimented like a martial art or dance classes.

It won't boost your confidence immediately, but eventually you'll gain some measure of proficiency- and being proficient at something physical can be a big help with confidence in general.
posted by BungaDunga at 2:49 PM on March 27, 2015

I can have ten men crawling up my ass, trying to "get to know me". The ones that go from friend to more-than-friend are the ones who make their intentions well known, and more than that, woo me. Joe Shmoe down at the bus stop might be selling himself harder than you.

Here's the thing. Anything a woman can do all alone, she doesn't need you for. You can be Mr. Nice guy and, say, take out the trash and think you're getting ahead, but we can take out our own trash. You can eat my cooking and think it's wonderful, but I can get that anywhere. What makes you any different, what makes you better than all the other guys I know who are trying to talk to me? How will I know in my guts that you will move heaven and earth to make me happy? You have to differentiate yourself, come correct.

A lot of guys talk, but they don't do. Make some gestures, do what "just a friend" wouldn't do.
posted by Grlnxtdr at 2:52 PM on March 27, 2015 [14 favorites]

I'm a woman and I have had similar bad luck when it comes to relationships (I, too, often question whether I am a part of the "relationship Elect" as you say), but yet at the same time, have been on the other side as well, the side of having a guy be really into me but me not returning his affections (which I guess is what's happening consistently to you?). I Nth the idea of online dating, since generally people on those sites are single and open to some type of romantic relationship (be it a hookup or an LTR) - there are some exceptions but in general, that's been the case (at least it has been the case with me). I recommend OKC and Tinder actually (when you are more selective with your right swiping than an Ivy League admissions committee, you will generally not get the kind of weird, creepy messages - I don't know how it is from a guy's perspective but using Tinder this way has been good for me). If you live in a large, metropolitan area, your options are fairly limitless as well online or through apps.

When it comes to women not returning your affections, I guess all the advice I can give to you is the same type of advice people give to women in a similar situation. Don't appear too needy, or try-hard (not saying that you are, just watch yourself for these tendencies b/c at least for me, they drive women away) and definitely don't act possessive or jealous, especially if nothing has been established between you guys (again, I'm not saying that you do act this way, just watch for these tendencies). I know it sucks, I really do, I have been there and I'm still there now (as in, I'm still single with no relationship in sight), but just keep looking, especially online, but also keep looking in real life. You say you're into radical left organizing, and as a leftist woman, I can tell you that the thing that leftist women like the best is when a leftist man shows himself to actually practice what he preaches, in a sense, like put all of your feminist and anti-patriarchal ideas into practice as best you can, especially when it comes to romantic relationships (again, I'm sure you are, this is just a friendly reminder).

Good luck! And I don't think there's anything wrong with you (much like there is nothing dreadfully wrong with me and yet I still have all these problems). I think most of all, you just have to make your intentions clear with women, whether you want a relationship or a friendship and don't attempt to become their best friend in order to eventually sleep with them or anything or then get mad if they reject you - basically, don't turn into a Nice Guy™.
posted by lana0112 at 2:54 PM on March 27, 2015

we're all pretty politically active, though this had not always been the case before I began refining what it was I was looking for

This is pretty striking to me. You've refined what it is you're looking for, and that's absolutely fine, but it also lowers the odds that you'll meet someone in your area, attractive to you, attracted to you, and available.

To the extent that dating is a numbers game, you'd be well served to note that you've opted to lower the number of potential partners, so it's not altogether reasonable to conclude there's something inherently undatable about you.

Yes, check your hygiene, express interest sooner, and all of that stuff.

In terms of coping/accepting this, please realize that in a sense you are preemptively rejecting many women with whom you might otherwise have sexual and/or romantic chemistry. There's nothing wrong with being choosy. Do keep in mind that you are, though.
posted by whoiam at 3:06 PM on March 27, 2015 [1 favorite]

Following up on your comment, "entertaining, vulnerable, authentic, and accommodating" defines an outstanding friend, but does not define an attractive partner.

Again, I really have to disagree with any argument that your niceness is the problem. I also don't think it's a matter of you waiting too long to make a move--if I'm single and meet someone I'm interested in, I'd still be interested a month or two later. With the woman you mention in your example, I highly doubt that timing made any difference. I think the issue lies in how you present yourself in some way- your confidence, as I said before, or your physical appearance. You say that women told you it's not your looks, but it's also unlikely that someone would tell you that it *was* your looks to your face. If you don't want to post a link to a picture here, feel free to memail me and I'd be happy to give you some honest suggestions of things you might potentially change- haircut or whatever- if you're interested.
posted by three_red_balloons at 3:25 PM on March 27, 2015 [3 favorites]

I have known a few guys who were well short of what I would consider "hot," but they always went for women who were 10s and didn't have any interest in women who were on their level.

sort of the flip side of this ... in Austin, my observation is that women can be MUCH more choosy than men ... if there is a mismatch in a couple, it's that the woman seems less objectively attractive than the guy. so average looking women are with quite attractive guys. and if a woman is objectively "hot," like really slender, fit, beautiful face, good style and poise ... nothing less than an Adonis will have a chance with her.

look around. figure out the sexual economy in which you live. is it an average looking girl's market? then you may have to "date down" lower than you prefer.
posted by jayder at 3:25 PM on March 27, 2015 [2 favorites]

oh, and ditto on the offer to evaluate your photo via email or memail. I think I've got a decent eye for these things.
posted by jayder at 3:28 PM on March 27, 2015

Absolutely try online dating. Trying to make your friends into girlfriends can work, but it's also complicated and fraught with danger for all concerned.

Maybe there's something wrong with you, but don't assume there is. It's all about the right guy meeting the right woman. It could be worth asking some of the women who turned you down to be frank about why they said no, but even then you may get answers that don't really help. It may be that there's no one reason, but they just don't feel a spark. Or they may say it was because of things you can't change, or don't want to change.

halitosis, maybe you're kind of effeminate, gross teeth?

Because lord knows no woman likes a guy with feminine qualities, and effeminacy is an awful flaw on par with halitosis and gross teeth. (Not trying to pick a fight, but that struck me as awfully heteronormative and gender police-y.)
posted by Ursula Hitler at 3:35 PM on March 27, 2015 [15 favorites]

> Wait, do you mean 1.5 months during which you see them in social settings a few times and then after 1.5 months you ask them out? Or do you mean 1.5 months during which you hang out one-on-one several times (once a week or more) and after 1.5 months you make a move by asking to kiss them?

In general, the former, not the latter. Sometimes the latter but if I were to give it a ratio, I'd say 80/20.
posted by KantGoOn at 3:40 PM on March 27, 2015

Yeah, you are probably nice and fun and entertaining but not at all edgy. You probably feel very safe and kind and easy to talk to, and eager to please. Those are things women like in a friend of either gender. Those are things women like in a date as well, but you also have to have confidence, sexuality, a strong sense of self, and the ability to take risks and make mistakes and laugh them off. You probably need some more "yang" - just more asserting yourself out there in the world, and being too cool to care about other people's opinions too much. I also get a little whiff of desperate here. I know it's hard NOT to be desperate. I get that. But it's so incredibly crucial. Maybe this is also what is meant by the advice to "live in the moment"- don't focus on outcomes and scripts and A to B. Just take what is, no expectations, and maybe things will surprise you. And make your desires known.
posted by quincunx at 3:40 PM on March 27, 2015 [1 favorite]

I think this article from lore, while written in a snarky tone, is actually a really nicely concise way of summarizing the usual stuff that's going on whenever someone talks to me about this. fwiw, I think this happens to people of all genders, not just guys, it's just referencing a cultural narrative that is guy-specific.

So to sum up lore's points really quickly, maybe:
1) you don't flirt at all and don't show a sexual side
2) you fixate on particular people and don't let go (probably not you)
3) you interact with women based on a role that you are looking for a woman to fulfill in your life, not based on their individual qualities
4) you try to approach dating/romance/flirting based on what you see in media rather than feeling it out and being yourself
5) you focus your attention really intensely on the people you are crushing on and they can tell that you are treating them really differently from other people; this tends to make people uncomfortable
6) you lack confidence and interact with women in a way that suggests you feel that finding the true love of your life will solve your problems (it will in fact create more)

I'm trying not to be snarky either, (I am just in a hurry), I totally get how lonely and frustrating it can feel. I think the things you can do right are very much what a lot of other folks here have said about stating your intentions early, but it's also true that sometimes you just have to be in the right place at the right time to find the relationship that works and it can just take a while. If you focus on being happy and confident in yourself as a single person and maybe find some role models in your life who show you that life can be really fulfilling without needing to have romance in it, I think it can really help with being more relaxed about this.
posted by capricorn at 3:41 PM on March 27, 2015 [5 favorites]

You don't need to be "edgy." If I can guarantee one thing, it's that turning yourself into Poochie the Rockin' Dog won't help.

It sounds like you've tried online dating and gotten many follow-up dates, so I really don't think you have a problem, except the problem all of us have: Dating is a numbers game and often sucks.

As far as the "friend" thing, think of it this way: You're good at making friends. While I get the frustration, no timing or "special move" or whatever is going to make people who aren't into you suddenly be into you. Sorry. So your choices are:
a) Get into all that mopey "friendzone" PUA bullshit about how "women don't like nice guys"
b) accept that these women aren't into you that way for their own reasons, and be happy you're cool enough they want to be your friend, rather than running screaming into the night when they see you coming.
posted by drjimmy11 at 3:45 PM on March 27, 2015 [4 favorites]

You have too much chalence on this topic. That is not a word but I will explain. When I was younger I played a lot of disc golf. When you take your first shot on a disc golf hole, you are allowed to run forward and throw the disc, trying to make it go very far and also aim fairly accurately. It is a complicated motion. We discovered that it was easy to overthink it and try too hard. Better to think about something else and rely on muscle memory to sort itself out. Better to be nonchalant, in a word. Mild substance abuse helps, I am led to believe.

"Chalence" therefore is the substance that you have failed to rid yourself of when you have not been non-chalant.

Sometimes you'd forget and think about your steps and your body twisting and the right time to release the disc and it would go hooking into the trees out of bounds and you'd be lucky to find it ever again. "Ah," we'd say. "Too much chalence."

So. You must take a break from thinking about this at all until you are rid of your chalence. Mild substance abuse may help. You are allowed to go on a date or whatever if you stumble into one, but you are not to think about it or work on anything or generally try at it. For a couple of months, find something else to work on or think about. And I think it will sort itself out.
posted by Kwine at 3:53 PM on March 27, 2015 [12 favorites]

It's not that I mind having more friends

IMHO, your title is the problem. You need to start with the perspective that you have enough friends and don't need anymore. If you find someone that you are especially attracted to, ask that person out on a date or 3, and if chemistry/attraction happens, then great. If not, "you have enough friends." Online dating may help simply because there is no ambiguity about why you are socializing with each other.

Outside of online dating, flirt and give your attention to those who flirt back, rather than giving your time and attention to people who don't.
posted by bright colored sock puppet at 4:06 PM on March 27, 2015 [2 favorites]

In other words, what Kwine is saying, is stop giving so many fucks. In my experience, stopping giving so many fucks about being in a relationship made me happier with myself. It didn't magically make the right person appear, but the fact that they haven't isn't really bothering me. And take a few more chances flirting earlier on too.
posted by Beethoven's Sith at 4:09 PM on March 27, 2015 [2 favorites]

You're a lively writer and your first 9 paragraphs supported your feeling that the lengthy no-relationship situation is a mystery. OTOH, the 10th and 11th paragraphs gave a whole different picture -- depression, self-loathing....

These things are picked up by others. It seems reasonable that you're also talking to the ladies about these things, because after all, in a relationship you have to be open about yourself and let them know who you are. I'm so sorry to be so downbeat, but that may be the explanation for your mystery.

I'm glad you're getting medication and therapy. Follow the above advice to enjoy all parts of your life, not just the dating part. That in itself will make you more attractive. I wish you all the best.
posted by JimN2TAW at 4:10 PM on March 27, 2015 [2 favorites]

I've seen these patterns before. And many times, the men they were happening to were men who were perfectly nice, good company and all that, but who did not make themselves known to be sexual beings. They simply did not show their sexual side. They were viewed as safe, as 'brothers', not potential mates.

So don't be like those men. It's okay to be a sexual being and it's okay to show it. Try making a risque joke every once in a while (not a gross one or one that's misogynistic, just a bit risque) or commenting on whichever celebrity you find attractive. Talk about sex when the subject comes up.
Let the people around you know that you have sexual desires. It'll help others to see you as potential boyfriend material.
posted by Too-Ticky at 4:10 PM on March 27, 2015 [2 favorites]

You can't see someone around for a month and a half, cultivate a neuter persona and platonic friendship with her, and then after six weeks of that expect her to want to make out with you. You missed your window at that point.

It's fine to ask someone out the night you meet them. Not "let's bone", but more like "hey, would you like to have a drink with me Thursday evening?" I get that you're still not sure you want to Be Dating them yet, but the point is to make that assessment in the context of dating.
posted by fingersandtoes at 4:23 PM on March 27, 2015 [16 favorites]

And indeed, a month or before asking someone out isn't especially long in activist time - these are all people you see once every week or two at meetings and events, right?

A month and a half of in-person physical contact is a fucking eternity in activist time. I have dated activists and for about four or five years dated left-activists exclusively. Each and every time, hook up or intent to hook up was initiated at the first meeting - or rather, the length of the first event. So if it was a three day event, "within the three days", if a three hour event, "within the three hours."

But here's the thing. There's a fucking lot of really sexy activists. And as a lady activist, you really have limited chances to get it right. You can date usually about three or four guys from inside the movement before it becomes a thing that impacts your organizing. Which means standards are higher - do I want you to be one of my four? If you're not smoking hot, uber confident, passionate, and brave? The answer is no.
posted by corb at 4:40 PM on March 27, 2015 [5 favorites]

I generally am not waiting a long time to make my move: usually about a month and a half or so of getting to know the person, and I have been making it a point to make my interest clear and explicit (through words) rather than beat around the bush like I did in college.

Holy moley what? No. Immediately after meeting, yes.

And you don't have to be smoking hot, uber confident, passionate, and brave. People are attracted to a wide variety of other people. Not every lefty activist woman is looking for the same thing, and actually that persona wears pretty thin in my experience.
posted by DarlingBri at 4:55 PM on March 27, 2015 [4 favorites]

Yeah, I think it's important that the only changes you make would be changes that are actually good for your life and will make you a happier person. Like, if you're kind of an idiot about modern pop culture, as a random for-instance, spend some time learning about what people are watching and listening to these days so you can actually talk about that stuff. Cultivating your "edge" is artificial and weird. Learning to dress nicely is fine. Trying to be "mysterious" is for chumps.

Be yourself, the very best version of yourself that you can be, and try online dating. If you follow that advice, I can pretty much PROMISE that you will eventually meet a woman who thinks you are the cat's jammies.
posted by Ursula Hitler at 5:03 PM on March 27, 2015 [3 favorites]

But when it happens over and over and over again, it does make me wonder whether there's something I'm doing wrong. Why is it I'm consistently viewed as good friend material, but not good lover material?

How many friends does the average person have? How many lovers, at any given time? It is in fact normally and totally appropriate for most members of the opposite sex not to be interested in having sex with you. It would be awful and awkward if the inverse were true--at least, after you were in a relationship.

It doesn't really matter, I don't think, how fast you move--I think the problem is more that the time between the two represents a big emotional investment in your part on something that doesn't yet exist. It doesn't matter if it was just destined not to work out, or if you made mistakes, or if she did, or whatever, because we're all human and both will probably happen a lot in your lifetime. The fact that some people find their life partner at 21 is just a combination of statistics and different standards. You could probably change your standards, but you could also just have a bit of patience and just try to make sure all your ducks in order for when it happens.
posted by Sequence at 5:12 PM on March 27, 2015

Cultivating your "edge" is artificial and weird. Learning to dress nicely is fine. Trying to be "mysterious" is for chumps.

I think I was the one who first broached the "edge" topic, so I should clarify. I don't mean suddenly affecting a tough-guy persona. I mean, quite simply, being more unapologetically yourself, asserting yourself and your preferences, not being such a "pleaser," etc.

The kind of "edge" I'm talking about is available to anyone, no matter what their personality.

No edge: Worrying a lot about how what you say will be received by the girl.
Edge: Saying things occasionally that are a bit obnoxious/pushy/etc.

No edge: Always being available to chat by text, and responding immediately. Apologizing profusely for any delay in getting back to her.
Edge: Telling her, occasionally, "I'm busy, can't text now," with no explanation.

No edge: Catering to her, even on things you don't like or don't agree with.
Edge: Calling her out on stuff, in a tactful way.

No edge: Always putting her first in scheduling.
Edge: Having stuff that you choose to do over her.
posted by jayder at 5:14 PM on March 27, 2015 [7 favorites]

Yeah, jayder is right. You don't want to be overly accommodating. Here are some things that people perceive as overly accommodating and obsequious: 1. Over-flattering the person. Did you go on and on about how wonderful her eggplant curry was? A simple compliment is usually enough. 2. Apologizing. Never grovel. Only apologize if you hurt someone's feelings or are late for an appointment. 3. Don't be too self-deprecating, but don't be overly arrogant, because in the first case you will look like a loser and in the second, a fool. 4. Don't put her first until you are in love with each other, but do make her a priority and follow through when you say you will. 5. Don't seek reassurance. "Do you like me? Do you really like me?" 6. Don't thank her for hanging out with you like she's bestowing a favor on you.

We women are just people and we don't like to be treated like royalty or idolized, especially activist women. It's too much pressure. Being edgy has to do with not being eager, sycophantic, and self-deprecating.
posted by Beethoven's Sith at 5:23 PM on March 27, 2015 [1 favorite]

Disagree with jayder. Edge is not games-playing. It's just having mojo. Mojo is just having a strong presence and a sexual intent. I laughed a bit at craig's reply, but he's not half wrong. Seriously, just work out. I'm not saying you need to reach maximum buffness, it's just that it'll put you in touch with your own physicality - your feeling of yourself in your body - and it'll increase your sense of competence as a physical being. You'll stand taller, feel more grounded, take up more space, your posture will improve. Also your libido is likely to increase. Some people have tons of natural mojo and don't need to work out to tap into it, but pretty much everyone's mojo is increased when they do.
posted by cotton dress sock at 5:33 PM on March 27, 2015 [5 favorites]

Cracking the code to the friend zone: Personally, when I meet a guy who gives no flirting signals and seems to just want to be friends, I let my guard down and feel "safe," and if I'm not, y'know, extremely attracted to him, it's a relief. If I'm a little attracted to him, it's still a relief. I imagine a lot of women feel the same.

If you're on the market and flirting with women you find attractive, these things will be resolved faster and you'll know who's a match and who's not. You will need some degree of social finesse to make non-matches into regular friendships and you might alienate more women with whom you'd like to be friends, but if you can find a good in between to being friendly and being flirty things will be OK.
posted by stoneandstar at 5:47 PM on March 27, 2015 [2 favorites]

(a relief because phew, a male friend I can just be relaxed and friendly with! Don't have to have the guard up because he's not coming on too strong! So if you're in that comfort zone it's legit hard to switch back, even if you would've been into the guy had he initially flirted.)
posted by stoneandstar at 5:48 PM on March 27, 2015 [7 favorites]

With respect to the people who are pushing the "edge" thing, I still say no. We don't know if this guy is a doormat, and I'm not seeing anything in his question to indicate that's the case. For all we know, maybe he's too pushy and selfish already! (I don't see anything to indicate that either, but again, we don't know.) And besides, there are women out there who will find a fumbly, shy guy attractive as hell.

If he needs to be more assertive in his life, he should do that. Anybody, male, female or whatever, should do that. But we don't know that that's his problem. Suggesting he should try to build up his "mojo" is making all kinds of sweeping assumptions about how men should be as a group and what women find attractive as a group. He is an individual, and he is trying to attract a woman who is also an individual. He needs to be his authentic self, not cultivate some persona.

KantGoOn, do not assume that you will be alone forever. The only way that will happen is if you totally give up on meeting somebody... and even that may not work, you still may end up in love. There are a gazillion women in the world, and you could probably fill a stadium with the ones who would be happy to make out with you. (Seriously, there are a lot of people on the planet, and even if only one woman in a thousand would dig you that still adds up to lots and lots of women.) Just keep looking, and eventually one of those women will be as happy to find you as you are to find her.
posted by Ursula Hitler at 7:40 PM on March 27, 2015 [7 favorites]

I suspect these women aren't physically attracted to you.

they've told me I'm not a bad looking guy and that there's nothing wrong with the way I look.

Would you want to date a woman who "wasn't bad looking and there was nothing wrong with the way she looked"? Or would you want to date a woman you thought was really cute?
posted by sunflower16 at 7:51 PM on March 27, 2015 [2 favorites]

I suggest you hire a dating coach. By interacting with you they will be able to see what's up much better than any one on the internet will.
posted by rancher at 7:57 PM on March 27, 2015

"Mojo" doesn't mean "macho" - it's just energy; to have it is be vital and engaged, to be at once rooted, embodied, in flow, and to communicate one's own essential force to others, it's got nothing to do with gender.
posted by cotton dress sock at 8:02 PM on March 27, 2015 [3 favorites]

[Folks, please don't turn this into a debate among commenters. Thanks.]
posted by LobsterMitten (staff) at 8:06 PM on March 27, 2015

Here's one thing that you should try which I don't think has been suggested yet: Ask a friend or two, preferably female friends, do go on a dating site, and pick out women for you to message. Even if you don't message these women, if nothing else, I think this exercise will help you gauge whether you are aiming for women who are "out of your league."*

i also think you should stick with the online dating, and I'll nth that you need to make your intentions known sooner. If you feel like there's some romantic potential, just go for it. Be up front about taking them on a date, and if they accept, start things out casually (but still clearly dating), and if things don't work out, hey, you can still be friends! I just know that after having someone in the friend category for awhile, I'm highly unlikely to switch them over to dating prospects. I hate the friendzoning thing, because that makes it seem like it's about some intrinsic qualities a person has, but really, I just have a hard time switching someone back into the category of romantic prospect, in the same way that if I first meet a guy who is dating someone else I know, I'm not going to see them as dating material.

As far as looks, I don't think you have to go start working out but if you don't do this already, you should definitely up your wardrobe game a bit. You don't have to be fancy, but it makes a huge difference if a guy is put together. Nice fitting pants, clothing in good condition, etc. I mean, I put a fair amount of effort into looking nice, so I'd like a partner who holds up their end of that bargain as well.

On preview, I do agree with the whole "edge" thing in the sense that you need to have a personality, where that personality is something other than "nice, friendly guy." You should totally continue to be a nice friendly guy, because as a twenty something woman who dates men, I can say that at this point I and all of my friends are going to go for nice guys. But I'm also a pretty opinionated person with a specific sense of humor and clear likes and dislikes, and we don't even necessarily have to have a lot of overlap in these areas, but I do look for someone who has a distinguishable personality. (And that's true for friends as well as dating prospects.)

*I hate that term, and that whole idea, but I do think this is a factor to consider.
posted by litera scripta manet at 8:24 PM on March 27, 2015

Oh, I meant to add that askmefi is really great at giving advice about online dating profiles, so you should definitely consider posting a question about how to improve your profile. Even if you've had friends look it over, there's also something really valuable about having total strangers give their impressions.

You come across really well even in the question you've written here, so I don't think you should write this off as some lost cause. It sounds like I'm in your target age range/demographic, and at least based on this question (and your username!) you sound like someone I would consider dating, so just don't give up hope!
posted by litera scripta manet at 8:30 PM on March 27, 2015

To pick up on this in your follow up:

I put a lot of focus on being entertaining which makes it tough to be vulnerable and authentic

I think you hit the nail on the head when you say it makes it tough to be authentic. I have a colleague like this; she's a constant stream of jokes and plays on words and irony and clever asides, and while she's a nice enough woman, I never have the feeling when I talk to her that I'm talking to a real person. Instead, I have the feeling I'm talking to a persona with nothing actually behind it. I'm sure that's not true, but it's the face she presents to me 100 percent of the time, and I always feel uneasy speaking to her, in the same way I'd feel uneasy talking to someone who always wore a mask.

And even apart from that, I find her utterly exhausting. I absolutely cannot be around her for more than ten minutes at a time, because it's a chore to interact with her. If I want to be entertained, I can go see a show and sit in the dark and not have to worry about whether I'm offending the performers if I don't laugh at the jokes. When I'm trying to talk to someone, I want to relate to the person, not to serve as her audience. That sort of thing puts a burden on me, because just as she feels an obligation to be entertaining, I feel an obligation to act entertained. That's not always where I am.

So yeah, if you do, in fact, spend a lot of focus on being entertaining, I might try dialing back on that for a bit and see if things feel different.
posted by holborne at 8:45 PM on March 27, 2015 [15 favorites]

When I posted my previous replies, I'd missed the OP's follow-up. So, he IS saying he's too accommodating, among other things. Well, I sure feel like a dummy now.
posted by Ursula Hitler at 10:11 PM on March 27, 2015

OP, the future Mr. Owlcat shared your struggles for a number of years. He's a sweet, cultured person who's a little shy, and while he doesn't give off any weird vibes, he also doesn't always attract attention. He and I were introduced by mutual friends, and while we generally liked each other on meeting, we didn't develop feelings for each other until we knew one another better--which, for a variety of reasons, took a few years. (However, making a move sooner rather than later is best in general--I don't recommend waiting around for a few years as a strategy!)

The main qualities that made me start thinking, "Hey, this guy would be a great boyfriend" were 1) he is demonstrably a great, loyal friend to his friends (and it helped that I had several years of anecdata from those friends to prove it); 2) he was going out and doing fun things by himself/for himself, and those things sounded interesting to me; 3) he was always reading or watching something interesting and had thoughtful things to say about it. I'm really baffled that he remained single as long as he did.

I suspect not a thing is wrong with you, just as not a thing was wrong with future Mr. Owlcat. He just needed to find someone who was excited about his particular brand of awesome. I can't promise you that you'll find true love on the margins of your social network, but I encourage you to take care of yourself, pursue things you enjoy, keep being a great friend, and try not to harbor suspicions that you are somehow deficient. It's not a guaranteed recipe for finding a partner, but your life will be better for it either way.

You sound like a great person. Have fun and be patient.
posted by Owlcat at 10:20 PM on March 27, 2015 [7 favorites]

Ok, so I've been here. And there's a lot of good advice in this thread.

First of all, I absolutely agree with the comments above about a lot of young women(and hell, young people. But because of the way dating mechanics tend to shake out it is usually women in hetero relationships) just wanting semi romantic attention and cuddling and not realizing it's pretty leading on behavior, or realizing and not caring. I've been on the receiving side of that, and pointed out to friends they were doing it.(or just given them shit, because even if oblivious its not great)

I also agree about the chalence thing.

But outside of that, my number one piece of advice is to quickly get yourself to a fork in the road moment.

What I mean by that is a point at which you could be rejected or accepted. Clearly and definitively. I think a lot of your issue here is behavior that's basically complex rejection avoidance. Smoothly coast in without ever doing anything too bold or popping any real questions.

Clearly ask women out on dates after the first couple times you hang out. Blatantly flirt. Ask them to come out to the bar after work/events in your group(if you drink. Hell, it can be bowling) where it's late night and obviously a non-platonic activity.

You should be asking if they want to make out the next time you hang out after the first date you asked them on. As a date. Using those words.

Yes, I've argued on this site before that no one uses that word anymore but
1. That weird shift in young people culture, especially among activist hipstery or kinda punk circles(which, like you, is where I'm at) is crap and leads to lots of this through its "casualness"
2. All my friends I've talked to this about I can think of right now were really impressed and in to it when someone of their preferred gender just stepped up and said "hey, let's go on a date"

The "smooth move" of let's just casually hang out and slide in to it thing only works if there was already a lot of tension. And critically, it usually starts with fairly aggressive flirting and maybe even sex and then backs off and builds from there.

So yea, put yourself out there to get rejected. Ask people out on dates. Early and often. It's not "creepy" and it's not counter to your activisty ways. It's up front and honest. Just be completely legit and friendly to people afterwards, not creepy or dejected and you'll be fine.

This also takes, and projects Confidence. Confidence is attractive.

I met my current partner of 5 years(we met 5 years ago today actually!) by approaching her at a party lots of both our friends were at, being my usual weird ass self, then chatting online a bit and just directly asking her on a date a few days later. It was a huge break from my typical "become friends and hang out for months and then try and move it forward" routine. It made a huge difference.

Change your script. Hell, I'd say the clearly asking for what you want and presenting yourself that way part is more important than being good at flirting. Some of my friends are awkward or dorky or weird as fuck, but they clearly put themselves out there. Shit works.

I don't think any of this has much of anything to do with how you look or physically present yourself. It's how you approach representing what you want to other people. I guarantee I know people soldier than you in some way who just... Ask. Someone you are attracted to will find you attractive if you present yourself in an upfront manner and don't give up after a few people don't reciprocate.
posted by emptythought at 4:10 AM on March 28, 2015 [7 favorites]

Don't rule out the possibility that a woman who is truly into you is perfectly capable of making the first move, too. It doesn't have to all fall to the guy and his "mojo" (seriously?)!

I don't think it sounds like you're doomed to a life of forever alone, you just haven't met someone who is into you. But if you do know sooner than a month and a half in that you "like-like" someone, make sure you're explicit and about wanting one thing and not another, as many other folks have said. Being direct is pretty sexy on the right person.
posted by Otter_Handler at 7:21 AM on March 28, 2015 [3 favorites]

inherently low-quality human being
Being in a relationship does not resolve this feeling. I see your point that not being in a relationship appears to be empirical evidence. But there are a lot of ways that you could find similar empirical evidence from within a relationship, too. The specific details can unfold in a million different ways, but it's not about the details--it's about how low self-esteem causes you to view whatever is happening, no matter what happens, as evidence of your inherent low quality.

For example, you might over-idealize your partner in the beginning. Like, wow, I can't believe this amazing creature would be interested in me. That can be a problem. And then after you get to know her enough to start to see more of her flaws and realness, and after the transition from "the woman I hope will date me" to "my girlfriend," your low view of yourself can start to rub off on how you view her as well. Kind of like the Groucho Marx line "I wouldn't want to join any club that would have me as a member," why would the man with low self-esteem want to date any woman who have the likes of him as her boyfriend?

Work like hell directly on your self-esteem. Not so much on what women think of you. Not so much on what one particular beloved woman thinks of you (either the current/recent interest, or the imagined and hoped-for lifelong companion). Directly on what you personally think of yourself. Maybe a loving kindness meditation would help: "May I be healthy and strong. May I be happy. May I be filled with ease."

how do I make peace with the fact that I will die alone?
When people ask this, I am never quite sure if they mean "I will never have a long-term relationship" or "I will never get married" or similar, because if that was their question, why not say it that way? If this is really, literally about dying alone, then I will say this: I hate the thought that my role in life is to be the eventual caregiver for a husband who will (this is partly my anxious worst-case scenario brain at work, but also not-unlikely based on stats) have a long difficult age-related decline, and precede me in death, and then after I've built up all that intimacy with him and invested all that energy into his care, I'll be the one who has to die alone, without him there to do for me what I did for him. So let's say you soon find a woman who will be your companion for the rest of your life, who will someday hold a loving vigil at your deathbed, and then live on without you, mourning the loss of you: how do you make peace with the fact that she will die alone? This seems like the real crux of your question, and it's a tough thing about the whole human experience, that no one can just say to you: here's the answer. Because we all die alone. And no one comes back afterward to let us know how it went. Even if there are loved ones nearby, holding their hand, talking or listening, the dying person always dies alone. Maybe a meditation on death would be helpful.
posted by Bentobox Humperdinck at 11:19 AM on March 28, 2015 [10 favorites]

This may or may not apply to you, so feel free to ignore if it seems off base. But one thing that some men do, out of what I assume are only the best intentions, is to actively avoid flirting with women or asking them out on dates. This is because they don't want to be "creeps" or "PUA jerks", they know that women receive a significant amount of unwanted sexual attention on a day to day basis and that they don't want to contribute to this. All laudable goals.

BUT, as people have pointed out, when you're attracted to a woman it is not more respectful to her to avoid flirting with her or asking her out on a date. In fact, it's actually disrespectful because you are not giving her the information she needs to make her own autonomous decisions about her social time and her sexuality. It can veer dangerously close to white-knight territory -- "She seems so great, I'm sure she gets hit on all the time so I will be the one to protect her from that!" As everyone has mentioned, it is also disrespectful to spend time with someone as a friend if what you really want is to date them. Let me tell you, it is one of the shittiest feelings to hang out with a guy and get close to them only to realize that they are interested in dating rather than being friends. Not that there's anything wrong with dating, I just want to know what kind of relationship I'm getting into and not have it sprung on me!

The thing that you need to do to not be a creep is not to never flirt with anyone, but to pay close attention to the other person and to immediately stop any attention or action that the other person is not enthusiastically consenting to. (You also need to never flirt with anyone who you have any kind of power differential over, such as a subordinate at work or a waitress.)

So if you are talking to someone at an event and realize you're attracted to her, you might lean closer to her or make smiling eye contact with her or touch her lightly. Maybe one time out of ten, she might respond by also touching you lightly, smiling, and maintaining eye contact. Great! You are flirting!

I would guess at least nine times out of ten, she might also respond by freezing, acting uncomfortable, looking away, or making shorter answers. Sad! She doesn't want to flirt with you! That's ok though, you're not a creep for trying. You also shouldn't take it personally -- she might only like ladies, she might have a partner, she might not be in the mood for flirting, she might not like flirting at activist events. Just immediately stop what you're doing and step physically away from her a step or two, maybe offer a quick apology ("oh, sorry about that") and try to continue the conversation. If she still seems uncomfortable, just gracefully exit the conversation ("well, hope to see you around") and let her be the next to initiate conversations with you.
posted by EmilyFlew at 12:10 PM on March 28, 2015 [8 favorites]

One female perspective to answer your question on indicating interest and showing attraction:

First impressions do count, but I have been known to change my opinions of people, especially if they are particularly extroverted (I get annoyed by this) or if they are not physically attractive. If they have super fun and nice personalities, this can and have overridden first impressions.

After the first significant interaction (20-30 minutes of chatting only with said person), I can tell whether I may or may not be interested.

After a second or third significant interaction in a separate context (date, or even just hanging out on friend groups), I will definitely know whether I want more dates and possibly a relationship at the end of it.
posted by moiraine at 10:18 AM on March 29, 2015

Try a 3-fold experiment.

1) Read this.
2) Pick a form of exercise, ideally an individual one, that you can set a goal within. Accomplish that goal; repeat.
3) Meditate. Here's a starting point.

Try these things. Perhaps you'll be amazed at the way you change yourself. Sit back and watch the difference in how the others you're interested in perceive you.

Consider setting a rule for yourself for 6 months: do not spend any one-on-one time with new female acquaintances unless it is ultra clear to both parties that it's a date. The only way to be sure is that you've asked them for a date, and used the words "date" or "go out". Do not make any attempts to upgrade friendships.

Also consider going online to get dates for the sake of dates. Join OKC and fully populate a profile. Sit down and send 15 short but thoughtful messages out to a broad range of women to whom you are attracted. Not 15 dream girls... just 15 women with whom you would be open to spending 1 hour. Note the results. Meet the women.

Worst case scenario: you get valuable experience in a zero-ambiguity situation. you experience first-hand the fact that certain women are attracted to you. friendship is not on the table to muddy the waters.
Best case scenario: you meet someone you really like!

It might be that online dating is not for you. But I'll wager the experience you pick up during the above will serve you well in whatever dating arena you ultimately favor.
posted by graytona at 3:37 PM on March 29, 2015 [2 favorites]

I need to focus more on being in the present moment instead of always comparing things to the past or future, I put a lot of focus on being entertaining which makes it tough to be vulnerable and authentic,

These two are absolute deal breakers for me. If I'm interesting to someone, part of the way I know that is their attention to the present moment. They're having such a good time with me, and they're invested enough in me, that they're not reaching for better times (past or future). Without vulnerability, there's no relationship. Stop being the funny guy.

Finally, I hesitate to say this in the thread, but. Being part of radical left circles makes dating hard. Radical Left Circles tend to be pretty judgey about the way people live their lives when they fail to live up to the standard. And, privately, most of us don't live up. We don't recycle 100% of the time. We occasionally use paper towels. We can't give up that one luxury and give more to charity. Whatever it is. Which can make getting close to people hard. We worry that they'll see the way we're not living up, and so we hide it. We hide our true selves and the ways we're falling short. We give up authenticity in favor of appearances.

In my experience, the way around this is to be the first one to show fault. Be OK with not perfectly living up to your ideals, and own the thing that makes you not a perfect activist. (I am talking about things like choosing the fancy plush toilet paper instead of the recycled kind, not like racism. I trust that this is an obvious distinction, and doesn't need further elucidation.) Don't bring it up in conversation or anything, just make your peace with it. Stop being slightly self conscious about it. Be authentic in your choices. Be authentic in your hypocrisy. (It pains me deeply that I'm a hypocrite, but since I've accepted that we're all hypocrites I have been able to be emotionally intimate with people in a way that truly wasn't possible before.)

Above all - watch The Tao of Steve. You need it.
posted by stoneweaver at 11:27 AM on March 30, 2015 [3 favorites]

The only thing I can come up with, is that you just want a girlfriend too much. Unhelpful as this may sound, the most desirable people are the ones who doesn't need anyone else in their life. People who really live life to the fullest or already have a girlfriend/boyfriend. I know this is a weird comparison, but I have had a lot of gay friends, and they have all expeirenced this phenomenom - I think it is even more obvious to them, due to their limited options.

I am saying this because you sound incredibly romantic and passionated,(this is a good thing) but perhaps your political activities is not enough 'outlet' for you to be satisfied. You obviously am very persistent, great with words, you sound energetic as well.
I think some increased narcissism would be the way to go. Take care of yourself, your body, your hobbies, forget about the girls. Seriously.
You need to experience everything life has to offer besides romance. To be so proud of your own accomplishments and excited about your own experiences that a girlfriend would be nice, but not an actual need.
If you really do suffer from severe self esteem/confidence issues,(I read you may have trouble with intimacy) it would take care of those problems as well.

Also, forget about the alpha male-thing someone has suggested. Being fully in charge of your own life and what you want for yourself is so much more attractive than being in charge of fleeting social situations.
posted by ParanoidAndroid at 4:46 PM on April 1, 2015 [1 favorite]

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