Searching for answers regarding lack of success in romance
July 18, 2015 12:35 AM   Subscribe

Why am I also so disappointed and unsuccessful when it comes to dating, romance, and relationships?

I know this is a hard question for internet strangers to answer definitively, but I'm hoping AskMe answers will be insightful as usual and some will hit on some truth, because I am having a hard and confusing time parsing it out.

I'm mid-thrities, female, mostly straight with most of my dating experiences being with guys. There have been 4 guys who I guess I could say were boyfriends- none of these relationships lasted more than 2 months, and most were ended by me because they were just not going to work, because I was not into the guy, the guy was not trustworthy, we had nothing in common, the guy was gay, or some combination of that.

Besides those "boyfriends" there have been hookups and very short-term dating situations. I am a late bloomer and didn't really start dating until after college, with a little bit of dating in college (just once person and not-quite-dating)

Besides that- I have had many close guy friends that flirt with me, act loving towards me, who I have had great chemistry with, who I was SURE were into me...and then when I expressed my feelings, they would say or indicate that they did not share those feelings/did not want to date me. EVERY time I've had a crush and confessed to it, I've gotten that reaction. Every time. Even when I was SURE the crush or attraction was returned. (this has happened a lot)

About me- decently attractive (although several years ago I was less in shape and didn't pay much attention to my appearance; these days though, I feel relatively confident about my appearance). I do get attention from guys, but they are always guys I don't know and/or am not attracted to. I am introverted but get along well with others. Very sensitive and emotional- intense and enthusiastic when I like someone. When I get a crush I get tunnel vision and can't think of anything else. I think of things related to romance in black and white terms.

Most recently, a guy at work who was always very enthusiastic about talking to me, always asking me what I was doing on the weekend and always remembering the answer, offered to help me do something I am trying to learn how to do- he offered several times.I took him up on it, we made a plan for the weekend, and he cancelled 3 hours ahead of time and hasn't been communicating with me since. Another guy at work (yes, I know I shouldn't be flirting at work, that's another topic) has been flirting (or what I thought was flirting) for months, we seem to have good I asked him to go to the movies and he said he has no time.

There are other examples. I've had deep friendships, great chemistry, experience attraction and it's not reciprocated or at least not expressed if it is (and I have usually asked).

Meanwhile, I've tried internet dating quite a bit; it has NEVER worked out- either I can't muster an attraction to the dates (most of the time) or I like the guy but he turns out to be non-committal or already in a relationship/only looking for sex. I will say that when I go on dates from the internet, the guys have usually been interested in seeing me again. I hate going on awkward dates and then rejecting the guy because I am not interested; it takes me a long time to build attraction and interest, hence why i get crushes on male friends; THOSE crushes are never reciprocated.

I'm really at a loss. My current theories are that:

1. I have an intense personality and am very sensitive, view things in a black-and-white way and therefore force guys into the choice of an all-or-nothing situation in which they would rather choose not to date me;


2. Something about me is unattractive (when guys get to know me, I guess) insecurity? being too intense? Negative? (I try to be a positive person but have dealt with depression)


3. I take guys' flirting WAY to seriously; guys flirt for attention but it doesn't always mean anything (is this true? but wouldn't it mean something SOMEtimes?)


4. The guys I like are out of my league? That would be sad. But I get crushes on guys who get close to and/or talk to/flirt with me; many of them I wasn't even thinking about before that. And I don't think I am so bad-looking.

5. I am afraid of commitment so I choose unavailable guys to crush on? (why would unavailable guys befriend me though?) It's true I am somewhat afraid of commitment and indecisive.

6. I'm too negative and intense to attract the guys I like.

That's all I got.

Does any of this sound familiar to the point where you may have an idea of what is going on, having recognized it in someone or yourself? I know you don't know me, but maybe something stood out, you have a guess, or it sounds like someone you know?

Again, I have had interest from guys,just not the ones I was interested in; I've dated guys, but it never worked out.

I feel sad and frustrated and lonely and would love to hear your ideas even if they may be inconclusive.
posted by anonymous to Human Relations (12 answers total) 7 users marked this as a favorite
I'm a man, long-married. I'm trying to imagine how a much-younger me would establish a longer-term relationship with you.

Consider what you wrote here:

I will say that when I go on dates from the internet, the guys have usually been interested in seeing me again. I hate going on awkward dates and then rejecting the guy because I am not interested; it takes me a long time to build attraction and interest, hence why i get crushes on male friends; THOSE crushes are never reciprocated.

You want an emotional and mental connection before acting on sexual attraction and interest, and more power to you! The practical result, however, seems to be that If a man has an initial attraction to you, it sounds unlikely that he'll get a second date. Few if any people can really establish a mental and emotional connection in one date.

Instead, you focus on men at work who you have gotten to know over a longer period of time. But, if those men are like me, they aren't likely to consider you for a romantic relationship, because (1) you both work for the same employer and they don't want to risk relationship fallout affecting their job, (2) there's your already-existing work friendship that could be imperiled, and (3) if there was an initial attraction to you, those men may have doused that flame months ago (rather than fanned it, as you perhaps have done), because of (1) and (2).

What to do? Maybe go on more second and third dates? Maybe find additional routines that put you in contact with men outside of work?

I'm not at all sure that I'm right, but I think my theory is much more likely to be true than that you have some character flaw that sends men scurrying away.

Best of luck!
posted by ferdydurke at 2:29 AM on July 18, 2015 [16 favorites]

This is a strange situation. It does seem that you are initially attractive but there may indeed be something about you that makes men less interested as they get to know you. That may be worrisome, but in some ways it's better than the opposite. If there was something about you that immediately drove guys away, you wouldn't get any interested guys at all! At least this way you have reason to believe you are attractive in some way, even if there is something about you that may be a problem when people know you better.

If you have some close friends, I'd suggest asking them. This could be rough, and there is the risk your feelings will get really hurt. But it seems like it may be the best way to get some idea of what may be going on.

I doubt it's your depression, unless you have a problem with being a major downer in conversations. If that was so, I suspect you'd already know that was an issue. It may be that you have a grooming, fashion or behavior issue that doesn't manifest every day, so you may be great on dates when you are trying to be your best but anybody who knows you well knows you are prone to scary mood swings or some days you dress like it's 1987 or some mornings your breath is really bad.

Unless you can ask somebody, I'm afraid it's kind of a guessing game. (But bear in mind, the person you ask may not give you the right answer even if they have the best intentions.)
posted by Ursula Hitler at 3:38 AM on July 18, 2015

Definitely try more second and third dates. Your approach to first dates is pretty sound – they really are for just meeting a brand new person! – and all you need is an additional perspective to use on second and third dates. First date: person throws up no red flags, seems attracted to you: GO for a second date. Second date: you start to get to know them as a person. Third date: this could be when it starts coming together.

As for flirting at work. I live in a country where it's basically an avowed pasttime (France). Being a sensitive, serious sort as well, and having been burned badly by a first experience, I took it upon myself to learn how to differentiate flirts from interest. Herein I share my wisdom in the hopes it may help you, fellow sensitive, serious woman. (In my nearly 40 years on this planet, I have never been interested at first. A man can be the most chiseled Apollo who ever existed and I'll be like, "yeah, whatever. What's his character?" With time, I have fallen in love/crushes with a wide variety of men if you only look at appearances.) There are people who totally go for flirty flirts and that's okay. They're different people, though.

First off, it's okay to flirt at work. Everyone has their own preferred degree; so long as you're aware of the risks of your degree of it, are honoring others' boundaries, and consent and all that good stuff, it's all good.

Men who flirt with you right off the bat are flirts. Cross them off your "potential interest" list. You don't want someone like this in a relationship anyway – in time you'll notice that they're either a well-paid salesman (which, again, if salesmen are your thing, that's cool), or known for being flighty. Or both.

Men such as those you have met who treat you like an office girlfriend, are looking for an office girlfriend. For me these can be the most heartbreaking. Some are so well-practiced at it you can see past the veneer easily. Others, especially those who aren't quite aware they're doing it, can make life really difficult. The best defense against office flirts is a good offense: ask about their life outside the office. If they don't share much, or change the subject, or never get past "I went to X, and did Y," they're an office flirt. If they do share, and pull something like your first example, it may have been genuine interest that fell through who-knows-why.

Then there are the very rare, genuinely interested men. The problem, when you're a serious sort, is that they're likely to be serious sorts as well, which is not a problem in and of itself, but one of working together. A seriously interested man at the office is going to look at it seriously: "shit, what happens if this doesn't work out? what could be the fallout? is she able to keep work and life separate? is she the sort who takes revenge on people when they disappoint her? does she communicate well with others?" These are all questions you should be asking too, obviously. The last two are possibly the most important: anyone who takes petty revenge on people who get on their nerves, is not someone you want to be in a met-at-the-office relationship with. They will do the same to you, only it will be multiplied by heartbreak. "Does he communicate well?" One reason the office can be a good place to meet people is that you see what people are like in all sorts of situations. Does the guy talk things out? Does he take responsibility for his actions and their consequences? Does he appreciate people and keep quiet when he doesn't, or does he gripe a lot in a way that contributes to office rumors? (There is a difference between private griping that doesn't leave a room, and public griping.)

You will find with these hints that the pool of potential office suitors is reduced to approximately nil. Sorry. I'm a consultant who meets with loads of people at all levels, and have worked in several dozens of offices over the last decade. And that's been my lived experience. On a more heartening note, I do know a few serious, sensitive people who've met one another in the office, and have wonderful relationships. They make it work by communicating, and keeping work and personal life separate. At the office, they work. No one would think to question their uprightness about it, and that even includes managerial couples I know (managers within the same company).

After reading all that you've probably come to another conclusion too: as you're able to get first dates outside an office context, that can be less fraught.

Also, I don't think it's you. I see this a lot with serious, sensitive women – most of my friends are just that sort. The happiest ones I know are those who ended up meeting the right person; one who honors their sensitivity, thinks their seriousness is a treasure, and finds them all-around adorable. It can take time. Serious, sensitive men go through a lot of the same experiences too, and can be just as wary as a result. As for me... I'm still single. I'm cool with it.
posted by fraula at 4:00 AM on July 18, 2015 [6 favorites]

This is going to sound unhelpful at first, but bear with me.

I used to be you. I was intense about crushes. I was a late bloomer. I had very few relationships and none lasted more than 2-3 weeks, tops. I'd always break off because I wasn't into the person I was dating. People who were into me? Nah. Then a longtime internet friend pretty much knocked me sideways when he declared a romantic interest. We have now been together ten years. Ten happy years.

So, what gives? I have acknowledged to myself that I need to know a person before I can get emotionally involved. I need to have an established friendship before I allow myself to be emotionally available. You going on one date and then crying off rings true for me.

Rather than going on internet dating which is explicitly about seeking a relationship, try to involve yourself in activities where you meet new people/make new friends. Try to establish a friend connection - this will allow you to be emotionally available in a way that going on endless First Dates will not. Find activities where being serious and sensitive is seen as a good quality - some sort of volunteering or maybe an outdoors activity that'll make you laugh and relax (again, I am projecting myself upon you).

I think the issue here is not that you are OMG!intense but rather that you need an environment that'll let you relax your guard and allow you to make friends that could segueway into be serious romantic partners.
posted by kariebookish at 4:30 AM on July 18, 2015 [7 favorites]

Where are you? Some cities have a relatively low single male : single female ratio and that makes dating there a lot more difficult for women.

Nthing going on more dates with a guy before deciding that you're definitely not feeling any chemistry. If you're not feeling the urge to kiss him by the end of the third date, *then* cut him loose. Also go on more active/exciting dates than the typical dinner-and-a-movie thing since excitement helps attraction along whereas if the date activity is boring your brain will associate that as the guy being boring.
posted by Jacqueline at 5:29 AM on July 18, 2015

So I'm not going to sugarcoat. You remind me of a friend of mine. She's smart, funny and fun. But she has terrible, terrible luck with men. Here's why:

1. She can be very negative, specifically about men. Probably a self-fulfilling prophecy or cycle. She often comments she'll just have a kid on her own, or that she'll marry someone who works all the time on purpose so she doesn't have to see him. These comments

2. She doesn't make an effort to look nice and doesn't seem to have learned the standard feminine grooming stuff like makeup, etc. It's not really that she has some kind of idoelogical opposition to it, either- she complains that others "look prettier" sometimes- it's that she either doesn't know how or won't make time.

3. She DOES crush on and pick men who are out of her league. In particular she's very focused on looks. When I started dating my wonderful loving boyfriend, she made some comments about how I was the more attractive one and he was lucky that I found pretty hurtful, actually. The implication was that she would never consider "dating down." She is also focused on hyper-masculine types who are "cool" or superficially charming. Basically, she doesn't consider the good hearted guy in the corner.

4. I think a lot of it is that she's hung out with her brother and his friend so much she acts like "one of the guys" a lot. She tends to act competitive and all "hey bro" with guys, which means they give her friendly attention but not specifically romantic attention. She's even proud of this, like "I drink beer and not girly cocktails" which has more than a whiff of internalized misogyny sometimes.

No idea if you're her, a lot like her, or I'm reading into it. But these things are certainly possible.
posted by quincunx at 5:43 AM on July 18, 2015 [7 favorites]

Give more men who are interested second and third chances. Give the guys who pay attention to you whom you don't know a first chance!

Ascribe little or no import to the friendliness of men at work. That's how you're supposed to act at work.
posted by MattD at 7:32 AM on July 18, 2015 [1 favorite]

Seconding ferdydurke. What jumped out most for me in what you wrote was that it's hard for you to find attraction in people you don't already know.
posted by rhizome at 10:29 AM on July 18, 2015 [1 favorite]

You remind me of me. I also had an extremely hard time with mustering attraction for people I met on dates, and though I didn't crush on people at work, I did wind up dating my way through my male friends until, at one point, I literally had zero straight male friends I had not dated at some point. I realized I had to stop just falling for any guy I was friends with, particularly because the aspects of a person that make him a compatible friend with me are not exactly the same aspects of a person that make him relationship-compatible with me, so I was frustrating myself and making drama and nothing good was coming of it. So I got older and I fixed it, and now I have advice for you. Here it is.

Keep going on internet dates! BUT: add something in your profile stating that you are looking for a low-pressure, friends-first type of scenario that, if both parties find themselves interested in time, could slowly, eventually lead to dating/a relationship. This will filter out fast-attracters: guys who have to get datey/physical right away or stop being interested. This is a lot of guys. But there ARE guys who are slow-attractors, who are less like this and more like me and you, and they will read your profile and be interested.

I met my boyfriend on the internet years ago, and while I didn't have a go-slow stipulation in my profile, circumstances were as such that we moved very, very, very slowly (he didn't kiss me until the 8th time we met--he thought I just wanted to be friends, because I'm stand-offish on dates because I can't muster the attraction right away, and I thought he just wanted to be friends, because he didn't try to kiss me). This was the only time a date-with-stranger ever worked for me and became a real relationship. Ever. So it can happen. You just have to set the pace. I recommend doing it explicitly and on your profile.
posted by millipede at 12:55 PM on July 18, 2015 [5 favorites]

You might have a self-esteem problem or some fear of intimacy if you regularly find yourself not attracted to those who are attracted to you, which seems to be the thread running through all your examples.
posted by kapers at 1:18 PM on July 18, 2015

You're disappointed because you keep blaming yourself and you keep thinking and telling yourself there is something wrong with you. Look, in the past couple of years (after leaving a very long relationship and engagement), I've dated a lot. Every elderly woman I've met tells me you have to kiss a lot, a lot of frogs. Because there are an infinite amount of frogs out there. And honestly, lots of accomplished and very attractive women are in relationships that they've settled for and their love and loyalty make them bear through it. They sometimes tell me, "Just don't get married" even though they love their husbands. Their husbands are good guys who love them so much.

Don't despair or beat yourself up. You kind of have to look at it all realistically and realize it's not your fault, you aren't doing anything wrong. It's not a failure. And it's not something that can be figured out.

Because having a boyfriend or partner is not a prize you win or get rewarded with for being great and perfect in all facets of who you are, how you act, etc. and a lot of women in "happy" relationships aren't as happy or not-lonely as they profess to be. Some are miserably in love and settling for so much less than they hoped for, and telling themselves that they're still happy.

The best you can do is to treat yourself with compassion and love. I think it's great that you're not making yourself date guys you're not attracted to---you not being attracted to them is not your fault. You don't owe anybody any chances.

I caution you against thinking you're better off in a romantic relationship than single or that a relationship can solve those feelings. And continue to be careful, because some guys are masters of manipulation, even the ones you're letting have a chance that you're not attracted to. Kiss frogs, if you feel like it, but not because you desperately want a relationship. You can find love and happiness in non-romantic relationships with friends and yourself.

Loneliness and despair is natural, please remember, it's natural. It's okay. Because letting loneliness and desperation drive you into finding a partner might put you in an extremely bad dating situation, or worse, in a horrible relationship. And there are lots of trapped women in those who are scared of the pain of having to detach from even the worst partner.

You'll be fine, honestly. It's not your fault you've dated guys that were wrong for you or that dates didn't turn into relationships and true love and happiness ever after. We'll all understand better much later in life why many, many women are staying single. But take solace in knowing that it's perfectly normal and you're not alone and it's not your fault or anything you're doing wrong that can suddenly be changed by a new hairstyle or dating boring guys who you don't find attractive.
posted by discopolo at 6:49 PM on July 18, 2015 [4 favorites]

I agree that trying to meet men in situations where you can let the relationship develop without pressure is a good idea. And I also agree that you may be reading too much into workplace flirting.

If you wanted to keep up online dating, I wanted to suggest posting a question here about that, maybe linking to your profile for critique. Also, I don't know which site(s) you are using, but different sites have pretty different demographics, and that makes a difference.
posted by mermaidcafe at 4:53 PM on July 20, 2015

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