Everyone is having sex in the library, but me....

December 30, 2007 11:57 AM

25 year old girl that hasn't had anything past a 2nd date in 6 years, what is wrong (if anything) with me?

So I will try to give you some background in as few words as possible. I'm a 25 year old girl in grad school. I've only ever had one very short lived and intense relationship when I was 18. My ex was the only guy I've ever had sex with and because the majority of our short lived relationship was long distance, I've only had sex a few times.

Since then I've gone on a pretty large amount of first dates, a few second dates and really nothing past that. I hook up with guys maybe once or twice a year on average (although I admit it has been happening a lot lately, never sex just generally making out and little more sometimes).

I'm usually described as being cute and while I'm rarely the hottest girl in the room, I think I'm generally above average and that isn't really my issue.

I have a sort of unusual background and unusual interests, I've traveled everywhere, I'm really overeducated, my family is such a disaster that it's actually funny at this point. I’ve suffered from depression on and off my whole life, but I have it pretty under control now. I have a pretty extreme sense of humor and while this makes me a lot of friends, I don’t think it really attracts the guys. (the whole men want women with a sense of humor to laugh at their jokes, not make them laugh) I’m pretty smart and a really good debater, but these are also things I think are more valued in guys than girls. Although, I have to say some really hot lesbians have hit on me, so if anyone ever comes up with a pill to switch sexualities, I’m set.

I find myself relegated to the friend zone with a lot of the guys I meet. I used to have this self esteem issue where I assumed it was because I wasn’t pretty enough, etc etc, but now I realize that really isn’t the case at all. I tend to meet guys, befriend them and then they end up dating one of my friends. On the other end of the scale, I occasionally hook up with guys I meet at parties (generally I vaguely know them through a friend/school) and usually I will see them again, but generally it fizzles out pretty quickly. When I meet a guy these tend to be the only outcomes, the friendships never develop into more.

There are two guys who I have had intense friendships with that I can probably best describe as platonic relationships. The first was my roommate who was in a very unhappy long term, long distance relationship. And the second was an extremely promiscuous guy, who was in his late 20’s and had never had a relationship. I no longer talk to either, which I think is a good thing, but I’ve had this dynamic to a much lesser degree with other guys.

The guys that generally are interested in me for a relationship tend towards the very geeky/socially awkward. Unfortunately, I have yet to meet one that I was attracted to. I have tried with one guy this summer, who wasn’t my type, but who I thought I should give a chance because maybe my problem was that I was being too superficial. It had disastrous results (no idea what he was doing with women and didn’t understand the word no in bed). I don’t think he’s a bad guy, it was just really clear that he thought real life was like the movies and had no clue what he was doing. He then wouldn’t stop calling me for 2 months. So I think there does have to be some physical attraction. I have to say I’m not that picky, I’ve liked a wide range of guys, but I feel like I was the geeky/awkward girl in high school and now I’ve grown up and found myself and I would like to find someone that was the same more or less.

I've dabbled in internet dating on a variety of sites. I admit I've never gone more than a month on any site, but it would usually go that I would be flooded with messages from guys, I would then start messaging a few. Most of the promising ones would drop off quickly and I went on quite a few first dates that ranged from the guy being a total freak, to him being nice but boring to kind of cool with zero chemistry. Essentially none were even close.

So the question is: Am I doing something wrong? Is there something wrong with me? Or do I really just need to accept that this is the reality for a lot of professional/smart women nowadays? Throwaway email account: [e-mail]

posted by anonymous to human relations (43 comments total)

No, there is nothing wrong with you - you sound perfectly charming and well rounded. That said, it is entirely possible to make it to 25 without having any type of serious relationship. I don't know if it is the norm or the exception for most women, but it is certainly not abnormal.

A bunch of people will chime in later that you've got to put yourself in situations where you'll meet people. Coffee shops, online dating, stuff like that is fine, but I will say that if you're of the mindset where you want to do something about your relationship status (or lack thereof) then you really should engage it at every level. That means engaging guys you meet in places other than parties or bars. If you show genuine interest in other guys (not just guys who you think are your "type") then your bound to find guys who will reciprocate.
posted by wfrgms at 12:09 PM on December 30, 2007 [1 favorite]

No, you don't need to accept that your lot in life is loneliness. You need to accept the fact that you're young and IT just hasn't happened to you yet. It will. I'm can't predict the future, of course, but my guess is that you're the type of person who will find love through friendship (rather than through tons of dates with strangers). The fact that this hasn't happened yet says nothing about the future.

I think you've said some very astute things about what makes you unappealing TO YOUNG GUYS. Young guys are dipping their feet into the water of life, and they tend to get scared away by women who challenge them too much. That's not the case with (many) older guys.

I started noticing a big change -- towards maturity -- in my peers (and myself) at around 25, so I'm betting you're just on the cusp of things getting better. When I was 22, you might have scared me off. From my vantage-point at 40, you sound ideal. (Sorry, I'm taken and too geeky for you, anyway!) I'm betting that if you think about it, you know smart, barbed-witted women who are in long-term relationships.

Just keep living your life, getting involved in studies and activities. Keep making friends. It will happen. It's a numbers game, but the odds are in your favor.
posted by grumblebee at 12:19 PM on December 30, 2007 [2 favorites]

family is such a disaster
pretty extreme sense of humor
I’m pretty smart and a really good debater

I'd start by considering these things. Hard to say without more details or seeing your performance on a date. Have you talked to a friend about this? Someone who knows you in person might have some insights. Humor and debating are fine, if kept to a friendly level. I always get a funny feeling about people who self-describe as smart. Could ego be a problem here?
posted by DarkForest at 12:27 PM on December 30, 2007 [1 favorite]

Do you have a close friend - male or female - who could give you an honest assessment of your dating style? I agree with wfrgms - you sound like a fine catch. But maybe there is some annoying quirk that you don't see. For example, I've been told I come off as very aloof, when in reality I am shy and just never learned to smile much. So I have practiced smiling - not Stepford-ish smiling for no reason, but in conjunction with a friendly remark, and I can feel the difference in how people react to me.

Good luck and don't lower your standards or change into something you are not.
posted by SuperSquirrel at 12:28 PM on December 30, 2007 [4 favorites]

You sound pretty normal to me. I wouldn't obsess over this too much (although I'm sure I did when I was in a seemingly very similar state!). For some women, and I think this is particualrly true for smart, well-rounded, active women, it just doesn't happen until later in life. Enjoy your freedom!
posted by otherwordlyglow at 12:54 PM on December 30, 2007

"...I’ve suffered from depression on and off my whole life, but I have it pretty under control now..."

Well there's yer problem!

Anything I say here is gonna look bad no matter how I word it, so I ain't gonna mince words. Even if you're a little depressed now and then, and who ain't, it's gonna show. You think no one notices, but they do. They may not know what it is but they know something's off. Depression is a loud obnoxious bird hanging around your neck and it puts people off.

I've suffered from depression on and off my whole life, and I tell myself I pretty much have it under control now. That's a lie. That's how we who suffer from depression get from sunrise to sunset. We lie to ourselves that we got it licked and we move on with our lives, but it's still there. Squawking.

The reason why the guy goes for your friend instead of you is cuz compared to you, she's more appealing. Less baggage and more fun.

So what do you do about this? Nothing.

I don't recommend you try to change for some guy. No man is worth you not being you. You don't need a guy to make you feel less depressed. Hell. We tend to make women MORE depressed, more often than not. He's not gonna complete you. He's not gonna ride in on a horse and kiss you and make it all go away. You're not gonna be able to hide from your own problems by solving his.

It's when you stop looking that it comes after you, and it'll happen when you least expect it and probably when you don't want it to happen. Cupid's a friggin bastard.

Accept yourself for who and what you are. If you can't do that, how can you imagine anyone else will? If he can't do that, whoever he is, why the heck would ya wanna hang with him anyway?

You can't make it happen. It either does or it don't. Anyone who says otherwise is trying to sell you something. Probably a self-help book on how to make 'it' happen.
posted by ZachsMind at 12:55 PM on December 30, 2007 [9 favorites]

You sound like a perfect candidate for Dale Carnegie's How to Win Friends and Influence People. As cliched as this sounds, take a look at this book. It really works, and there are plenty of transferable lessons if what you really want is to Win a (boy) Friend.
posted by Mr. Justice at 12:56 PM on December 30, 2007 [1 favorite]

Student of Man, I really think your comment was uncalled for. I don't understand what gave you the impression that the OP is stuck up, besides her mentioning that she had a good sense of humour, is intelligent and good at debating, all of which give us an idea of what kind of person she is and does not seem irrelevant to the question at hand.
To the OP: You sound like you would be a wonderful girlfriend. While it is true that being intelligent and unafraid to show it can be offputting to some guys, you could think of it as a filter that keeps out the ones you wouldn't be interested in anyway. Granted, you don't seem to have had much luck with that so far. I think part of the problem could be the self-esteem issue you mentioned. It is possible that since you believe that you are unattractive in some way, this leads to your behaving defensively on dates, leading to your date not liking you as much as he might have and so on in a vicious circle. Don't know if that really makes much sense. Anyway, just wanted to say you sound like a really interesting person and I'm sure there's a guy out there who'd want to be with you, so don't lose heart.
posted by peacheater at 1:02 PM on December 30, 2007 [1 favorite]

I’m pretty smart and a really good debater, but these are also things I think are more valued in guys than girls. Although, I have to say some really hot lesbians have hit on me, so if anyone ever comes up with a pill to switch sexualities, I’m set ... The guys that generally are interested in me for a relationship tend towards the very geeky/socially awkward. Unfortunately, I have yet to meet one that I was attracted to.

You said you haven't been with many guys? It shows, because at that age, the guys who exude the sexual confidence of a 40 year old CEO on his lunch break are few and far between. Because outside a few very attractive, outgoing (promiscuous) guys, at that age, most have not had a lot of experience with girls, despite what you might believe. I don't mean experience in a 15-year old fumbling with a bra way, but experience in the category of, "Oh shit, finally! I haven't got anything in 5 months, so excited, so excited what do I do, what do I do."

You don't have to slut it up to find a guy that clicks, but you definitely have to put yourself in a position where awkward things happen. Smart, outgoing, sort-of-geeky guys also have the same problem. They want the charismatic, good looking girl in the room. Usually it takes until 25 or so until they realize the handful of make out sessions a couple times of year is sort of lacking and embrace other people's foibles.

I am not saying find a guy you aren't attracted to, but find one who you are kind of attractive to. Ask him out for coffee/lunch/drinks. Don't start a relationship out with an awkward, drunk makeout session and wonder why you can't find any guys. You might find some guys are a lot more interesting and entertaining. It is a lot easier to train a guy to be good in the bedroom than train them to not be a bore to talk to.
posted by geoff. at 1:05 PM on December 30, 2007

I'm usually described as being cute and while I'm rarely the hottest girl in the room, I think I'm generally above average and that isn't really my issue.

Are you sure that isn't an issue for guys?

*ducks behind wall*

Sorry, I'm sure you really look fine, but in general if women are getting less attention than they want, it can be because they aren't projecting an image of attractiveness or availability. This has less to do with your actual appearance (no, you probably aren't fugly) but the way you dress or hold yourself has an effect.

Also, you need to give online sites more than a month. OkCupid is an AskMe favorite for good reason. (also, I met my honey through there). Look for people who are highly compatible. If you don't find the person attractive at all, you're not going to be turned on very much, and that's going to make it hard for you to enjoy sex whether the person knows what he's doing or not. You really won't know until you meet them in person, though, since some people do not photograph well (I look horrible in most photos, but look okay in real life).

Don't just wait for people to contact you on the dating site, go ahead and contact the ones you like. Try to be a bit mysterious/flirty (don't say things like "I really liked your profile" or "You sound awesome") and try to move straight to a meet as soon as possible...don't get involved in a lot of back and forth messaging. Just get a feel for whether the person is psycho or not, then meet them at a public place.

I say this as someone who has been lousy at dating in general but has never managed to have a second date with someone and not get involved in a long term relaionship.

Oh! Right! I nearly forgot! The first night is always going to be lousy. Just give it another go and it should improve.
posted by Deathalicious at 1:11 PM on December 30, 2007 [1 favorite]

I agree that you sound pretty terrific and you'd probably be a great girlfriend. You don't seem to have a shortage of first dates, but maybe you're having trouble signaling that you are available and want a little more. I have friends like you, every single one is a hot, smart woman but they can't close the deal. One is the most gorgeous woman I know (a graduate student, like you) and she hasn't had a boyfriend in six years. Please take heart, and know that there is nothing wrong with you. Just know that being the hottest girl in the room is nothing compared to feeling like the hottest girl in the room.

First, stop being so down on yourself ("I'm rarely the hottest girl in the room"). It's really hard to attract another human being when your own opinion of yourself is "meh." Sometimes, new clothes and a hair cut are all that is needed to make you walk with a little confidence. Also, if you are usually a conservative dresser, try going just a little out of your comfort zone, a skirt an inch higher or a blouse just a little lower can change your frame of mind.

Put yourself out there and think of what a great deal everyone you date is getting. You are a smart, responsible, hot woman and a catch. You are merely weeding out the losers who can't recognize that.
posted by Alison at 1:17 PM on December 30, 2007 [1 favorite]

I don't think it's possible for a bunch of strangers to answer this question based one what we know. I second the advice that you ask your friends (male and female) about this. I also second the advice that you ignore Student of Man.

It's a tough thing. It's hard to know what you want from a relationship without having the experience of going through a few relationships that don't work (at 25, I was just starting to get a clue).

Other than that, just keep at it. Internet dating in particular is characterized by a lot of first dates and relatively few second dates, so don't think that's about you at all. During the time I was doing the Internet-dating thing, I went on dozens of first dates, a handful of second dates, and three third dates. But I also met my now-wife through Internet dating.
posted by adamrice at 1:17 PM on December 30, 2007 [1 favorite]

it was just really clear that he thought real life was like the movies and had no clue what he was doing.

Did we date?

Anyway, here's the thing, most (young) guys don't want a woman who will challenge them. I'm willing to be you think you're smarter than most people, which you probably are, but fellas in their early/mid 20's ain't generally pleased by that. You keep attracting dorky/socially inept guys because they're the ones lookin' for a dominant/challenging woman. Not to say you should attempt to change your personality, or settle, but you need to accept the difficulty of the situation. Some people are widely compatible and widely accepting with the general population. You're not one of them.

In short, it ain't anything you're doing or not doing (at least from the detail given in your post); you're just swimming against the tide of your age group. My one active piece of advice is to watch the line between challenging/holier-than-thou. There's a difference between being smarter and acting superior. Other than that, keep being social, keep your feelers out. I'm willin' to bet the odds of you finding a spark will only increase with time.
posted by Roman Graves at 1:19 PM on December 30, 2007 [2 favorites]

I agree with the suggestions upthread that you should ask a trusted friend, one who is willing to be painfully honest, the question you asked us here.

I have a friend named Karen who could have written your question. She is smart, pretty, funny... and can't get into a serious relationship.

What Karen has a hard time seeing from the inside, but which is readily apparent from the outside once you've come to know her, is that she inadvertently broadcasts a strong signal of clingy desperation when she is on a date or otherwise interacting with a man in whom she's interested. She also has a bit of a tendency to become conversationally competitive when a subject comes up on which she has knowledge. For whatever reason, Karen doesn't seem to read the verbal and non-verbal cues coming from the other person with whom she's interacting, at the point where he is becoming turned off by what she's saying or how she's saying it. She simply doesn't receive those signals... and then the conversation ends and she "wonders what was wrong with that guy, amirite?" And, she used to have terrible halitosis (mostly due to a smoking habit she's now kicked).

I'm not saying that you have bad breath and the dreaded whiff of desperation, Anon -- but I am saying that, as with Karen, there could be other factors blocking you that you can't possibly see from where you sit. And if you can't see them, you can't describe them to us to help you solve. Someone who knows you personally, on the other hand, could be a big help.

Another possibility, albeit one I recommend with hesitation, would be to look for a personal coach. If you don't want to put a close friend in the understandably difficult position of having to answer the question "What's wrong with me?!?", you could hire someone to fill that role. But, I am skeptical of most people out there who call themselves "life coaches," since anyone can claim that title and take someone's money for it -- you'd have to look very critically and carefully for a service provider that was reputable and wasn't just a swindler.
posted by pineapple at 1:20 PM on December 30, 2007 [3 favorites]

i've said this before and i'll say it again: meeting someone you click with is a complete crapshoot. you could be putting yourself out there or you could be taking a break and not looking, you could have an awesome personality or you could be a psychotic bitch, you could be smart or you could be dumb, you could be supermodel gorgeous or you could be a troll, etc. you get it. none of that stuff matters. not really.

you sound a lot like me and my girl friends (smart, funny, great careers, nice cars, cute houses, etc) for years i'd wondered what was the matter with me. and for years all my friends, guys and girls, had no idea why i couldn't find anyone either. i would look. i would not look. didn't matter. then right before my 35th birthday this past fall i met the perfect guy for me and we hit it off right away. it's not that anything's changed with me or my situation that made me any more attractive (in fact, actually, i'd been having a pretty crappy year trying to deal with a major recurrence of my depression) but that my number finally came up in that lottery.

so, sorry, there's no advice here really that will make you feel better (believe me, i'd heard it all). you might meet someone tomorrow, you might not meet him for another 10 years. but you're 25–enjoy your 20s. have fun with your friends, make out with cute guys, do your thing.
posted by violetk at 1:38 PM on December 30, 2007 [3 favorites]

I'm a guy. A real honest-to-goodness Guy. And I'll be your contrarian voice today.

I will focus only on the "can't get a second date" issue, as the long-term stuff is generally too complicated to deal with via AskMe. Too many variables.

I think I'm generally above average and that isn't really my issue.

No, you're not and yes it is.

OK, it's part of the issue. Sometimes ... OK, most of the time ... guys want sex first and questions later. So, your level of hotness and perceived sexuality factor is not enough to overcome your relative level of hotness. Guys will stick around for more than one date with a hot girl, or stick around for more than one date with an average girl if the sexuality quotient is significantly high. Note that I'm not saying, "guys want easy girls." Guys want sexual girls. Note the difference.

The guys that generally are interested in me for a relationship tend towards the very geeky/socially awkward.

You're giving off the wrong vibe and are therefore attracting the wrong guys. In other words, you are choosing the wrong guys, likely unconsciously. This may have something to do with self-esteem issue.

Prescription: Exercise. Makeover. Build confidence. Break out of your shell and go looking for guys in different places: You like books? Go rock climbing. Own a cat? Borrow a friend's dog and visit the off-leash park. Coffee drinker? Hit a martini bar.

Go be astonishing.
posted by Cool Papa Bell at 1:39 PM on December 30, 2007 [4 favorites]

I have friends who could have written this question, too. What's funny is that I see the opposite of the problem pineapple describes- I see people who are too good for anything and everyone (of course, they're not- they're insecure and use it as a wall), and they don't want to do X, Y, or Z because "eh, whatever", and they hate everyone they meet, and then they wonder why they're alone. If you haven't met anyone you click with, you haven't met anyone you click with- it's not because you're too smart or too cute or whatever. That's just life. It is kind of a game, and it stinks to be rejected, and it stinks when things don't work out, but you have to be able to pick yourself up. When you begin to be even a little bitter (i.e. "men want women with a sense of humor to laugh at their jokes, not make them laugh"- what a crock of horse poo, put all that out of your mind immediately), people can smell it, and it's really unattractive.
posted by ThePinkSuperhero at 1:44 PM on December 30, 2007 [8 favorites]

Take the initiative. Don't wait for relationships (or sex) to happen because a guy takes the lead. Take the lead. Most guys are so shy and victim-oriented today they need a leg up to get a leg over.
posted by A189Nut at 1:47 PM on December 30, 2007

Let me second Deathalicious' suggestion: OKCupid is a fine dating site. Moreover the outcome of their personality test was way more on the mark than I was prepared to admit.
posted by willem at 1:52 PM on December 30, 2007

I was single for ages before I met my current BF and I am smart, charming, fashionable, etc. (and obviously quite modest). I agree with pineapple that there may be some sort of social dynamic happening that you're not aware of. In my case, my friends all told me I was coming off as extremely "intense", which I didn't understand at all. It took me several years of therapy to understand that "intense" meant "argumentative and aggressive". Now, we can debate the gendered nature of "aggressive" as a negative personality trait, but it's not something you look for in someone who you're flirting with.

Overall, don't get down on yourself and try to take the whole dating thing as lighthearted fun, not an endless hopeless referendum on your worth as a human being (I was very bitter by the end of my singlehood). I hear women all the time talking about how they loved playing the field, and I wish I had had that type of confidence when I was single. But honestly, it's a crapshoot, totally. I tried online dating, Craigslist ads, blind dates, getting set up by friends, going to every social event known to humankind, and none of those things worked. And don't freak about your appearance, regardless of some of the clumsy answers above; look around you, there are plenty of very average looking girls in relationships and being a "10" or a stunner isn't any sort of prerequisite to having a boyfriend. Just keep putting yourself out there; if there was a magic formula for getting a boyfriend, it would be bottled and sold in the back of Cosmo and advertised on late-night TV.
posted by alicetiara at 2:16 PM on December 30, 2007 [2 favorites]

It's when you stop looking that it comes after you,

Yup.

You know, I've never been on a "date" in my life, but I've had a fair amount of great sex, a few enduring relationships, and even a couple of instances of real live honest requited love.

I met these people at school, at events of common interest, in the course of normal life when I was doing all those other things that don't involve trying to get laid, and I was never looking to meet any of them - or anyone at all, actually.

You're too hung up on this, and people can tell, though probably not consciously. People are attracted to people who don't need them because people who don't need other people tend to be pretty self-sufficient. And self-sufficient people are the ones with the best stories. (I'm certainly not saying I'm a model of self-sufficiency, but it's interesting that those aforementioned folks have always come in to my life when I've been most deeply involved in my work, my art, my studies, my engaged play, etc.)

Living your life for it and your sake also has the added bonus of being a great salve for that depression you mention.

People can be happy single. We are built to flourish in the right relationship, but we're also built to be pretty powerful on our own. A new intimate relationship should be a lovely surprise, an intensification and confirmation of existing happiness, not something you need to be happy. If you're not happy single, it's because you're not happy, not because you're single. Deal with that, not with your "dating technique" or whatever.

It's when you stop looking that it comes after you.
posted by poweredbybeard at 3:01 PM on December 30, 2007 [5 favorites]

Follow-up from the OP

geoff: I'm not talking about only being attracted to suave/whatever guys, when I say these guys are geeky, I mean the geeks of the geeks. I hang with a group of people who by definition were not the cool kids in school. I have no problem with awkwardness, I think it's unavoidable in the beginning, but that really isn't what I mean. I mean what happened to me this summer was one step above date rape, I had one guy friend who thought I should report him (it wasn't quite that bad, but it really wasn't acceptable either). I'm fine with shy and a little awkward, but there is a limit.

deathalicious, Alison, Cool Papa Bell: I don't think my problem is looks, I didn't want to come off as a total bitch, but I dress very very well. The years in Europe are good for something.

Also, I wasn't very clear in the original post, but I would say 3 times out of 4, I turn down a second date, so it's not so much that I'm not asked, but I'm not interested. I think this is mostly the result of me going on a lot of first dates with guys I know I probably am not interested in (or have just a little bit of interest/attraction) because I feel I need to give more guys a chance if I'm going to get anywhere. I don't think this is because I'm so awesome, I just think most of the time they think I'm nice enough and want to sleep with me.

My problem is more getting first dates with the kind of guys I want and I definitely meet a fair number of guys I would be interested in, I just usually end up their friends after a polite brush off (I'm not throwing myself at them, it's more I flirt a little, they make it pretty clear it isn't reciprocal and we all pretend it never ever happened and stay friends, as is life).

Someone I'll keep anon emailed me saying that while it wasn't PC, part of the problem may be my sense of humor makes me seem too masculine and girls just can't get away with the types of things guys can. I think this is really true, unfortunately, and may be a big part of my problem. I don't know if it's something I'm willing to change, as it's a pretty major part of my personality, but I may try a little experiment, like just shutting up and looking pretty for a month and see if things are any different. Maybe I need to hold back until I really get to know someone, I'm not sure. Of course I kind of feel it's a crime to not tell a great joke when you have one, but then again I also like sex, so it's probably a choice I'm willing to make if that's really the issue.

Thanks for all the advice, even the brutally honest stuff!

posted by jessamyn at 3:04 PM on December 30, 2007

I just want to nth all those who noted that your (and guys') age group makes a difference. I know it sucks to be told "just wait," but IMO as a fortymumble woman, there is a vast, VAST gulf between twentysomething and thirtysomething guys. Really, it's like night and day. And I think the same goes for women, too. Maturity makes people less picky and demanding, gives them social skills, and makes them easier to get along with. Twentysomethings can have lots of rough edges that only life can sand off. Maturity means mellowing - not always, but often enough that it's become my rule of thumb, that somewhere around twenty-eight to thirty, what astrologers call the Saturn return, is something of a magic moment.

For those of us who are "different" in some way - quirky or intellectual or spiritual or not conventionally attractive or what have you - the twenties, especially the early twenties, can be a real dating wasteland. Life gets better as you get older. Really.

Three pieces of advice for the here-and-now: One, don't let yourself get crushed or embittered by your lack of dating success. Repeat after me: Lots of good women (and men) are in my same boat. Ask me about the dating wastelands I've gone through (and survived)! There is nothing to be ashamed of. Two, learn to love your own company. This will not only get you through dating wastelands, but will make you a much more appealing person to any man worth having. And three, keep your horizons broad; don't be too picky about superficial qualities like race, age (within reason - you don't have to date 70-year-olds!), income, or height.

Good luck - and remember, yours is a common situation. "Sex and the City" exists only in fiction. Far more terrific people are wondering where all the good men/women are than are out there club-hopping in their Manolos and dating Mr. Big.
posted by Rosie M. Banks at 3:33 PM on December 30, 2007 [1 favorite]

Someone I'll keep anon emailed me saying that while it wasn't PC, part of the problem may be my sense of humor makes me seem too masculine and girls just can't get away with the types of things guys can. I think this is really true, unfortunately, and may be a big part of my problem.

I have never in my entire life had a problem finding guys to date and I have aggressiveness and masculine qualities in spades (and I am neither a supermodel nor dating total losers). I don't know what is causing you dating difficulties, but I really do not think this is your problem. Perhaps you do not know how to flirt? Masculine humor and aggressiveness can actually work quite well in flirting, so long as you know where to draw the line.
posted by ch1x0r at 3:35 PM on December 30, 2007 [1 favorite]

I think you need to keep meeting people. I get along quite well with guys, especially geeky guys, but it's really hard for me to click with someone - romantically, intellectually and/or sexually. I'd say it's only happened about two or three times in my life and even then it was just one or two out of three of the above. The only time I was able to connect with someone both sexually, romantically AND intellectually was with my husband. And until I met him I was pretty convinced that for whatever reason, I was meant to be friends with guys only, never as a romantic partner, because I wasn't like other girls.

But I feel really lucky to have found him because we are both total weirdos and can be completely ourselves with each other. A lot of women in my husband's past think he's a total loon (in a good way!) and I know that, while I don't come off as intimidating to guys, I'm a woman who doesn't like to dumb herself down or just bat her eyelashes and look pretty. And my husband loves that about me.

Are my standards wicked high? Probably. But I'm not willing to be someone I'm not for the sake of a long-term relationship. Causal sex, maybe, but for long-term companionship - well, this me, this is what you get.

My husband and I met online, btw, on Friendster.

I think you sound really cool and I think you shouldn't change a thing. But I also think if you meet more guys the chances you find a guy who likes you the way my husband likes me will increase. I liked online dating because at least it was getting me out there, meeting people. If that feels too contrived to you, I'd just start doing more activities you like - is there a photography course you've been thinking about singing up for? A painting class? Take it. Not just to meet people but to do something and explore yourself a little bit.
posted by sutel at 3:47 PM on December 30, 2007 [1 favorite]

I think this is really true, unfortunately, and may be a big part of my problem.

Coming from a guy's point of view, I disagree entirely. Sure that kind of humor can land you directly in the "friend zone" if it encourages more of a commradery relationship (I suppose in a lesbian friend kind of way). But it's not the issue if other factors are not present...one of them is a sense of sincere (read sincere but non-desperate) interest. Guys love attention just as much as women do, but often in a different way that I think could seem foreign, a lot of it is simply feeling respected or admired (kind of a power status...without it many males new to dating will be too agreeable/wussy, and thus interest and chemistry plummets)...while jokes are great, too much emphasis on them can build a barrier (this is a funny cute girl, instead of this is a girl I want to get to know more of and be closer to). Part of that is simply figuring out how to send the right signals...if you get those down it really matters less what you say if a good chemistry is there.

You're in luck however, as this is comically an easier task for women than men. We lack the female equivalent of wuss-dar in many circumstances which can end things before they start, it's simply a tougher game all round for us. Use that to your advantage ;)

Also if you find a guy you find a guy that you think tells funnier (or equivalent) jokes than your own...pursue that! Most of all have fun, open up, and put yourself out there. Too much focusing on what might be wrong will work against you like a self fulfilling prophecy (speaking from experience).
posted by samsara at 3:56 PM on December 30, 2007 [1 favorite]

Keep rolling the dice. They'll come up sevens soon enough.
posted by Ironmouth at 4:30 PM on December 30, 2007

I doubt there is anything wrong with you, but you are not getting what you want, and that sucks.

We can't really know you from this thread. But many people don't come off the way they think they do. I'm not saying that you probably aren't likeable and that you might have serious problems. It sounds like you are likeable. But you may well be sending off signals that you don't mean to. I think it might be worth talking to people-- friends, people you trust, perhaps even a counselor-- to see they have any insight. DO NOT ASK WHAT'S WRONG WITH ME! Ask them if you seem like you want a relationship, or if you seem open to guys, or if their first impression of you was misleading. I say this because it sounds like you want more than you are getting.
posted by gesamtkunstwerk at 4:54 PM on December 30, 2007 [1 favorite]

For a second I thought I wrote this question, except I just turned 26. I've had some serious relationships, but the last one ended over two years ago. I lived in Europe for a while and other places abroad. My family is great, but they are also a disaster. I've also suffered depression on and off from the time I was a teenager and tend to gravitate to geeky guys.

What I've found that has worked for me is going outside the scope of what makes me comfortable. Meeting people whether it be friends or guys that are "not my type," or that I think I won't click with. I've found that I do click with people that are very unlike me.

For example, a while ago I met a guy through a friend that I thought I could never date. From a superficial perspective, he seemed like a "bro" (complete with white tank top & lifted truck). After getting to know him, we started dating, and although we didn't match for other reason (each of us have our own problems to deal with), we're really good friends. Although I know this isn't the outcome you're looking for, we did go on many dates and he introduced me to different groups of people, which led me to other people

As someone said above, it may be a possibility that you might come across as intense, many people have told me the same thing. It doesn't meant you have to change who you are. My friends tease me for being a smarty-pants world traveler, I don't care. That's who I am, and there are men out there who like smarty-pants word travelers like you and I.

So, basically, just step outside your comfort zone a little bit and meet people who you might think you won't click with, if you do, that's great and they might introduce you to some really great guy who will want to go on date and after date with you.

Drop me a me-fi mail, if you want to commiserate and I can let you in on some other things I've learned from my own dating fiascoes.
posted by wilde at 5:05 PM on December 30, 2007

Someone I'll keep anon emailed me saying that while it wasn't PC, part of the problem may be my sense of humor makes me seem too masculine and girls just can't get away with the types of things guys can. I think this is really true, unfortunately, and may be a big part of my problem.

again, you're looking for a reason when really and seriously there is no real rhyme or reason. i've had ppl tell me i was too intimidating, too smart, too pretty, too this too that, not enough this, not enough that. i have had a majority of male friends all my life and have been told i had a strongly male perspective on sex and relationships and a masculine sense of humor, and i've also been told that i am too girly about other things. like i said before, it's a crapshoot. accept it.

I don't know if it's something I'm willing to change, as it's a pretty major part of my personality, but I may try a little experiment, like just shutting up and looking pretty for a month and see if things are any different.

stop driving yourself nuts. stop thinking that if you changed your sense of humor or something else about you that is perfectly fine, you'll find a guy. seriously? get over yourself. do you really want to be with someone who wants a girl who sits there, looking pretty and is too afraid to say anything lest her personality drive him off. because, ew. it isn't about trying to turn yourself into someone else because you think that's how you're gonna get the right kind of guy. stop looking for a reason and start really being okay with who you are.
posted by violetk at 6:12 PM on December 30, 2007 [3 favorites]

the friendships never develop into more

I'm getting a vibe that you're trying to turn your friends into your boyfriends. That works for some people, and then for people like you, it doesn't work at all. You need to get more dates in places where people don't know you yet. Don't start off as friends and then try and switch gears into something more.
posted by 23skidoo at 7:17 PM on December 30, 2007

I don't think my problem is looks, I didn't want to come off as a total bitch, but I dress very very well. The years in Europe are good for something.
I think you might be misreading this: people aren't saying you're not pretty enough, they're saying (I think) that good looks and very very good dressing can be intimidating to a 22-year-old mope. And to the kind of guy they're not intimidating to, he's looking for something a bit different than lots o' chatter.

Also: it's not the humour. Guys kill for a girl who can make them laugh. At least, they do here in Europe. Come back.
posted by bonaldi at 7:17 PM on December 30, 2007

I think you sound great, too, and you remind me of a lot of women I know. What struck me about your question was describing your intense friendships with two men as "platonic relationships", and I could be way off (obviously) but you strike me as the type of girl who is not actually looking for a relationship. Because it's incredibly easy to hook up with guys you aren't particularly interested in, while secretly pining within the safety of an "everything but" friendship with guys you fixate on. So many girls do this, and the longer it goes on, the harder it is to grow out of. If I were you, I'd question why there's such a divide between men you're attracted to who put you in a "friend zone", and men who are attracted to you who you put in a "friend zone". Because despite what the kinds of people who use terms like "friend zone" would have you believe, there isn't some secret, perfect hierarchy of attractiveness that dictates some scientific level of mutual attractiveness. If the men who you want to be with invariably wind up considering you to be friend (and not girlfriend) material, it's probably something that you're doing. Either you're working up crushes on guys who "reject" you because it feels safer, or you're presenting yourself in a de-eroticized way to men you're attracted to because it feels safer. The fact that lesbians hit on you with greater frequency, probably has something to do with how, as a straight woman, you aren't bringing your spooked baggage into those interactions.
posted by moxiedoll at 7:59 PM on December 30, 2007 [1 favorite]

Nthing the "you sound great" sentiment... maybe your "problem" is a lack of confidence? Or maybe you're looking too hard? I know that once I gave up, my girlfriend of 3 1/2 years practically fell into my life.

If I were single, I'd ask you out...
posted by fvox13 at 8:10 PM on December 30, 2007

I'd say give more guys a second chance. You might think they're not for you, but push yourself a little. I mean, don't go on a second date if it's a disaster, but if it's just unobjectionable meh, give it another try. If nothing else, consider it practice for honing the way you present yourself (whether it's about your sense of humor, debating, or anything else). It's safer to reject them quickly, before they reject you. Look for their good points and find something endearing about them. Get out of your comfort zone a little.

I've been in a similar situation, and I know it's hard and frustrating. You sound great. But there really is a point where logic ceases to help. Good luck and don't give up.
posted by bassjump at 8:25 PM on December 30, 2007

I think you sound great; when I was single, I was looking for someone just like how you describe yourself. In fact, rereading your initial post, in many ways it could have been written by my now-partner, down to many of the details. I don't think you need to worry that "something is wrong with [you]" or that you are making all the good guys run away. There's no such thing as too funny or too pretty or too smart (although someone who thinks they are any of those things can be pretty unbearable to be around).

But that doesn't mean that everything is peachy and you should just bide your time because true love inevitably shows up when you aren't looking. For example, I think that the guys you are describing sound like incredible duds. Really, really, not in your league. You need to start finding, approaching, and dating guys of your own caliber. Just because you were geeky in high school, and like hanging out with smart people, doesn't mean that you need to settle for dating guys who are socially awkward to the point of needing to be arrested. You need to start finding guys who are self-confident, who have at least a bare minimum of social graces, and who can connect with you on the experiences and ideas that make you who you are.

You write:

I'm not throwing myself at them, it's more I flirt a little, they make it pretty clear it isn't reciprocal and we all pretend it never ever happened and stay friends, as is life

I think you need to be much more forward. There are a lot of ways to do that, from going up and saying "hey dude, how about drinks on Thursday?" to following those Rules-style guides; either way, the key is that you take on a much more proactive approach than just "flirt a little" and back off before anyone is forced to say "no" or "yes" explicitly. On-line dating is great for this, especially as a woman, because there are so many possibilities, and you can keep looking at new ones as you sort through the last batch. But if on-line dating doesn't work for you (I didn't like it at all when I tried it; it's not for everyone), try something else. Break out of your comfort zone, since what you are doing now sure isn't working for you.

But like others have said, it sure is possible that you are giving off serious "I am not interested vibes," or you maybe have some weird quirks that are off-putting, or something like that. I mean, "confident" is great and sexy, but "up yourself" isn't. There are similar fine lines between "funny" and "mean," for example, as well as "can tell cool stories about my travels and family" and "talk all the damn time," etc. So if there is someone who you really trust, and know in person (not on the internet where someone like you who is really good with language presents really well), who would give their honest opinion of what is working and isn't for you, that might help.

And we all know people who say all day long "I'm looking for a partner!" but really they are doing everything they can to insure that such a thing will never happen -- they date people who clearly will never work out; they cut off relationships that look positive; and so on. There's no way to know if that is you or not from what you wrote here -- for example, are you dating such duds because you can't find better, or because it is a really easy way to self-sabotage?
posted by Forktine at 8:58 PM on December 30, 2007

Take one part Cool Papa Bell, 2 parts ThePinkSuperhero, mix well, and you have your answer.

deathalicious, Alison, Cool Papa Bell: I don't think my problem is looks, I didn't want to come off as a total bitch, but I dress very very well. The years in Europe are good for something.

See that right there? Whatever motivation made you make that statement, you need to suppress. Even if you are beautiful, that sort of attitude would come off as violently unattractive to most guys I know.

There is an, admittedly, very fine line between confidence and arrogance, but that statement blows over it pretty handily. Also the multiple references to your intellect and your "sense of humor" seem a bit belabored.

I don't know you so I'm not suggesting you are not intelligent and funny, but you sure seem to be bringing it up alot, which could be because you are either arrogant or insecure, and either are a liability come date time.

I think you need to spend some time deciding who YOU are, and that will help you immensely in finding the right kind of guy.

Most guys in their early/mid 20's will like you just fine in jeans and a sweater. The kind of guys you would want, anyway.

And of all the reasons I've ever heard for a guy to not pursue a girl in the last 20 years, I've yet to hear "too funny", so you would be wise to abandon that pretty quickly.
posted by Ynoxas at 9:39 PM on December 30, 2007

2nd or 3rding the recommendation to look for slightly older men, for the same reasons given above. I could have written a similar question a couple of years ago, and look at me! -- now I'm married.
posted by liet at 9:52 PM on December 30, 2007

3rding or 4thing slightly older man, are you in LA area? Keep trying, you'll meet your match someday.
posted by zengargoyle at 11:26 PM on December 30, 2007

One more from the OP:

Thanks!

Wilde: I think the "intense" thing was definitely true when I was a lot younger, but I've mellowed a lot and I don't feel the need to win (or begin) every debate that is thrown in front of me anymore.

Moxiedoll: I think you really have a point. It's hard to really see subtle things like that in yourself, but I think it is possible that I act differently when I like a guy. I used to be really shy when I was younger and maybe I sort of retreat to just being friends because it's safer or I don't know how to relax with them.

Bonaldi: yes the non Americans out there have always been good to me, of course part of that is probably the novelty of being the American girl also.

Ynoxas: Here's the thing, it's very hard to give any sense of what sort of person you are, unless you give only negative traits (in which case you will be called out for not having any confidence), without coming off as arrogant. I don't walk around proclaiming how nice my shoes are and how simply charming and precocious I am.

Is my perception of myself entirely accurate? Almost certainly not, especially when it comes to degrees of things. And come on I threw that in while admitting to not having had sex in 5 years, life long depression, a screwed up family, and nearly getting date raped.

And with the funny thing I don't think its so much guys going oh she's too funny I'm not interested, I think its more of a subconscious turnoff. It's great if you can turn it into a flirty thing, but I think my humor is a lot more random and in the spur of the moment than that, I think trying direct it towards some purpose would be really forced for me.

Also, I should say just by virtue of where I live and my sort of work/school group that I mix with, most of the guys I date are somewhat older. But say under 34 or so. It's funny because I've actually found that it's the younger guys who are a lot less cynical and bitter about relationships and women in general. A lot of the older single guys seem to have sworn off relationships and just want to sleep around. Of course this may have something to do with the kind of 30 something guys I know, rather than just 30 something guys in general.

posted by jessamyn at 7:30 AM on December 31, 2007

You are, according to your own words, an intelligent, funny, pretty woman who can debate well. There are many men who would be entranced by that set of guidelines. The 'intelligent' and 'debator' qualifiers, in addition to the geek background from your youth which you describe, does tend to skew you a little towards the "attractive to geeks" quotient.

I don't think you're wrong to believe that physical attraction is necessary. These are not friendships but romance. However, if the man pleases you in other ways, you may wish to see if physical attraction develops secondarily or as a result of emotional bonding, as opposed to using it as an initial qualifying agent.

My own two cents on the situation, and I will admit to a ton of bias on this, is that you need to find a slightly saner version of the guy from the summer. By any set of requisites, someone who doesn't understand nor accept the word "no" when said either in the bed or at the end of a relationship is not a person with whom a functioning adult romantic relationship can really be made. (Not knowing what to do with women, that can be taught, either from books or by the woman if she is so inclined and he doesn't think he knows it all already.)

I suppose the reason I am having problems parsing your statement to give you is advice is that it seems that the entirety of your post is more a set of negative requirements. This is not what I want, nor is this; I've tried this and discovered that this doesn't work for me, and so on. My suggestion would be to start looking at the situation from positive requirements. What attributes -- both physical, mental, and emotional -- are you looking for in a man, and how important are they to you? For example, you might say, "A man I meet MUST be 6'2", blond, and ripply, but MUST also have black hornrimmed glasses." Of course, that would severely limit the dating pool you've got to select from. Or you might just say, "Physical fitness is a sort-of requirement but not necessarily a dealbreaker. Blond hair and tallness are not requirements at all, but are definite pluses if the guy has those attributes."
posted by WCityMike at 9:46 AM on December 31, 2007

This caught my eye: "I have a sort of unusual background and unusual interests".

People of both sexes with unusual interests find it hard to meet other people with both similar interests AND mutual attraction. Also, as you've noticed, those with unusual interests tend to be on the more geeky/awkward side of things. So I'd say cast your net out wider.

Just as it's extremely hard to find beautiful, intelligent women with unusual interests, so too is it hard to find hot, smart guys with quirky pursuits.

Oh, and regarding the whole "guys are scared of girls who challenge them"; I call bullshit. There's been a lot of twitter on the web and in the press that guys only go for dumb beautiful girls. That's just a stereotype that belongs in the 50s just like the one about wives in the kitchen. I know LOTs of guys who find intelligence fiercely attractive. And some who run towards more intelligent and more successful women, not away. Regarding the blokes who Ms Journalist meets at speed dating and refuse to talk to her because she has a PHd: you don't think those guys are even worth talking to even if they did show interest. They're the self-absorbed scum that just perpetuate the stereotypes and make life miserable for the rest of us. Bah humbug and all that!

OP: Go find a real man, they're out there. You just need to keep looking and look wider.
posted by whycurious at 2:51 PM on January 1

Hi. I asked almost the same question before under the cloak of anonymity ages ago, and got pretty much the same answers. Oh, for the record, I'm about to turn 33, and I've been single for 9 years. (Mercifully, I've had sex in the interim. Thank god for Casual Encounters.) It is frustrating because with every year I become a better potential partner. I become a better person and I feel more and more ready. But? Violetk is right: total crapshoot. Disregard the "stop looking" business. It'll happen on its own time whether you are looking or not. Letting go of the idea that there is something you can do is actually very freeing, because it lets you off the hook of the feeling you're doing something wrong or not doing something right. You might have to let go anew every day -- I often have to mentally step back this way -- and I won't tell you it's always easy or fun. But it's possible. In the meantime, just make sure you're living your life the best way you can for your own self. There have been no easy answers for me but time passes anyway and you only get one go-round in life so I try to keep living for me and not for a partnership that doesn't exist yet. I have a hardcore unrequited crush so this is extra hard.

I honestly think we could start a club of us, for the number of rad-but-similarly-love-challenged women I've encountered through their threads and mine. If there's anything you get from my post let it be that you're not alone.
posted by loiseau at 11:22 PM on January 2 [3 favorites]