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Tuesday, August 19, 2008

Savage Love Letter of the Day

posted by on August 19 at 12:09 PM

Another letter that’s way, way too long for the column. It’s all below, after the jump.

But my advice? This frustrated after-the-jump straight girl needs to play to her strengths—the tomboy thing—and stop regarding/presenting her lack of experience as some sort of millstone that she will one day hang around the neck of some unlucky guy. There are guys out there that are actually into tomboys; and inexperience, when it’s properly presented (think “a sexy opportunity for a more experienced partner to blow someone’s mind and mold someone sexually,” not “a horrible, horrible burden for the more experienced partner”), can be a major turn-on.

Also, people who rule out bars and internet personals and rebuff the assistance of their friends can’t complain about how little action they’re getting. Don’t like bars? A large percentage of the people in them feel the same way; they’re there looking for someone they can never go to the bars with again. Internet personals make you feel gross? Yeah, well, being single is making you feel worse. And if your friends offer to drag you places, let ‘em.

I am a 26 year old straight girl, and unfortunately, I am not writing to you about my sex life. Rather, I am writing about the total lack thereof. I’m 26 and have never had a boyfriend. There’s lots of reasons for this—I am horribly, painfully shy; I never outgrew my “tomboy” phase and spend an inordinate amount of time correcting peoples’ mistaken impression that I’m gay (I am aware that many gay folks have to spend inordinate amounts of time correcting mistaken impressions about their not being straight, and I’m sorry for that; also I wouldn’t mind people thinking I was gay if I felt like my straightness was also perceived and respected some of the time [or if I was getting laid], but since my straightness is apparently invisible, my perceived gayness is aggravating); I don’t feel comfortable hanging out at a lot of the places where my peers/friends seem to hang out (ie, bars), so I don’t really meet a lot of people (and even when I do go out, my shyness takes over, and I don’t talk to anyone I don’t already know). Maybe I’m just profoundly unsexy and unappealing. I don’t know. I don’t know why guys are never interested, I just know that they’re not, and as I get older, I am less and less okay with my perpetual chastity.

I have had a couple of “near misses”—guys who were friends of mine which then moved beyond plain ol’ platonic friendship. In one instance, the guy was the one who initiated the making out, in the other it was me, but both times it was the guy who backed off. Both guys cited my lack of confidence as an issue (though not the sole reason they ended up being uncomfortable with the change in our friendship). I think my lack of confidence is entirely understandable and predictable if you spend more than ten seconds thinking about it—in a situation where someone else has lots of experience and I have none, of course I’m going to feel out of my element and hesitant and intimidated, no matter how well I know and trust the boy I’m getting naked with. I can’t just pull confidence out of thin air. I have to build it. To build it, I have to have experience. But it’s no fun to get naked with a girl with no confidence, and thus, the vicious cycle continues. And it just gets worse and worse as I get older and it becomes less likely that I’ll meet a guy with either as little experience as me, or a guy who doesn’t mind that I don’t have any experience who also isn’t creepy.

I’ve tried, in my own socially awkward way, to put myself out there. My friends try to take me places and encourage me to be outgoing. I tried one of those online dating services once, but the endless perusal of profiles made me feel like I was grocery shopping in a gross sort of way. I have thought about calling a male escort service, to get some experience if nothing else, but I don’t know how to find one and I’d feel even more shy and stupid than usual trying to explain this situation to someone who has sex for a living. I’m aware that I’ve painted myself into a corner here, and that I haven’t given myself any sort of out. The reason I’m writing now is that one of the near-misses I described just happened a couple weeks ago, and I feel a new sense of futility about the whole issue. A year or two ago, I just figured I was a late bloomer (which I always have been, my whole life) and was a little frustrated but mostly okay with it, but now I have trouble believing that any guy is going to want to spend any time getting past all my awkward shit and want to be with me, and I have more trouble envisioning a scenario in which I’m willing to let a guy in on all this. I don’t want to have unreasonable expectations about a guy’s ability to solve all my problems for me, but I’m noticing that those expectations are creeping in anyway.

I know I have no self-confidence but I do have some self-respect. I’m smart and I’m caring and loyal, people seem to laugh at my jokes, I’m fun to be around once I’m over my initial awkwardness. I’m not drop-dead gorgeous but I’m not ugly either. I know I have a lot to offer to the guy who’s lucky enough and persistent enough and patient enough to get past the shyness and the lack of confidence and the lack of experience. It’s just that the confidence issue and the shyness have, in this particular area of my life, reached epic proportions, and I’m starting to feel like it’s unfair to lay all that at the feet of any guy. Do you have any ideas? Do I just keep waiting not-so-patiently? See a therapist? Grow a new personality? Invent a time machine?

Please don’t try to make me feel better by saying, “I know this guy, So-and-So, who didn’t get his first kiss until he was 37,” because the thought of having to wait another 11 years for this part of my life to get started is kind of unbearable. I say this preemptively because it seems to be my friends’ favorite way of trying to make me feel better. It doesn’t work.


Tired of Being Single

RSS icon Comments


Forget this for now--go listen to today's podcast. It's fabulous! I laughed and cried--see if you can figure out which caused which. Seriously Dan, great responses today.

Posted by Beth Fuller | August 19, 2008 12:18 PM

Anxiety therapy! If you never relax, you're screwed. Get out of your head and into the world around you.

Posted by robo | August 19, 2008 12:36 PM

Shit, I get to give some advice?

I'd say -- first and foremost -- try to take some pressure off yourself. Skip the therapy and agree to help yourself. Relax and enjoy your own personality. You have as much a right to be you as everyone else has to be themselves. Don't worry about how much self-confidence you have, just concentrate on doing things that you like to do and acting how you really like to act. Be brave about it. Guys like that, and there's every kind of guy out there for every kind of girl. Someone's gonna dig what you're all about as long as you can let it out. Everybody takes a different trip; go ahead and enjoy yours.

Posted by Lloyd Clydesdale | August 19, 2008 12:39 PM

You do have confidence. You're quite confident in your ability to fail at relationships. But you don't have experience and thats what you need.

Throw yourself at people and get rejected. Ask guys out on dates and get turned down. Start conversations with strangers and talk about lame, dumb shit. If you fuck-up a whole lot, you'll get plenty of experience, then you'll get better at realtionships.

Sounds like fun, huh? No? Well, that's too bad. Everyone has to go through the fucking up phase. Better to do it when you're 16, but doing it at 26 is still better than doing it at 36.

Posted by blank12357 | August 19, 2008 12:42 PM

Between the long length of this letter and the self-defeating tone, this reeks of someone who is over-analyzing everything.

Rather than tell her to suck-it-up and go to bars or internet personals, I would tell her to fucking relax. Reading her letter stressed me out, and I imagine her "near-miss" suitors felt the same way.

This is something you normally notice (at least, on your podcasts), Dan, so I'm surprised you didn't on this one.

Posted by Mahtli69 | August 19, 2008 12:44 PM

I can't decide if it's a perk or a drag of a job that people can feel completely comfortable sending you crazy long letters.

Posted by Gloria | August 19, 2008 12:44 PM

I was exactly the same way, except for the perceived gayness, a couple of years ago. blank12357 @4 is right, just start making mistakes. After a while you get over not being able to talk to people and then you'll be able to talk to guys without caring what they think of you, which I think is the problem.

As far as the personals go, I met my current girlfriend of 2 years via Craigslist, so it can work. Start simple, trade emails with someone who seems interesting, then meet for coffee or a drink in the late afternoon. You have to start somewhere. The best way to gain confidence is to just stop caring about it anymore. Stop letting it bother you. Go in with the assumption that nothing will happen, essentially assume the worst and be pleasantly surprised if anything comes out of it. I think that's a good philosophy for life in general.

Posted by pragmatic | August 19, 2008 12:49 PM

TOBS, you're 26 years old. You're grown woman. And yet you apparently have not yet learned that getting what you want in life almost inevitably requires stepping out of your comfort zone.

You want to get laid. You want male companionship. But you also want these things to happen while you continue to wallow in shyness and self-loathing. Honey, it don't work like that.

Posted by Hernandez | August 19, 2008 12:52 PM

If she's a tomboy she should take that tomboyness and use it to meet men. Play sports? Join a co-rec league. If it's more nerdy forms of tomboy, like a gamer...join a gamer group. As for confidence, do what the rest of us do. Either fake it until you make it, or drink until it isn't an issue.

Posted by J | August 19, 2008 12:57 PM

Seven lines of text should never be contained within parentheses. If she talks like she writes, she’s not getting enough oxygen to her brain to fully utilize it in the process of attracting a mate.

Posted by PDX_Paulie | August 19, 2008 1:02 PM

re-fucking-lax! my little sister was in a similar boat, until she got to college. i realize that's younger than you but that doesn't make it irrelevant. the point is that she had a change of environment, lost a little weight, met some new people who had no previously-made opinions of her, and she was able to no re-invent herself, but become a better version of herself. she met a couple of guys, and is now, at 19, in her first relationship, which is rocky as hell, but it's because they are both learning how to be in relationships the way that i was doing when i was 13. my advice to is find some new hobbies, get used to meeting some people outside your normal social group (turning friends into lovers is not always the best way to go), accept help from your friends, and CALM DOWN! you already said you have a lot to offer people, work on believing that, because honestly the choice is yours. and as dan said, many people, myself included, love breaking in a rookie at the love game. present it as something exciting and not a hindrance to yourself and potential mates, and it will become exciting and sexy. but don't take my word for it...

Posted by tobes | August 19, 2008 1:04 PM

LOL with 10. All this navel gazing means she's missing the people checking her out.

Which is a kinder statement than my original reaction: tl; dr.

Posted by Emily | August 19, 2008 1:06 PM

This letter describes me to a tee five years ago; in my case, you would add a religion clause and abstinence until marriage, but it was a moot point. I had my first boyfriend, and my first kiss, when I was 28 years old. I never had vaginal intercourse with the guy, but there was plenty of foreplay and oral sex. Despite my inexperience, shyness, and lack of confidence, he made me feel amazing, and he taught me what I needed to know to fill the gap. He was an ass and we broke up; I met my husband shortly after that. In between I had a great sexual relationship with a platonic friend who I still hook up with for amazing sex when I'm in town. There usually seem to be some awkward moments to get over in these situations, but the bottom line is that you can't worry about whether you're doing it right or whether you look funny; take your clothes off and do what feels good and forget your inhibitions. And if you haven't started masturbating (I sincerely hope you have), it's about time. You need to know what makes you feel good and be willing to show/tell with a partner.

Posted by Isla | August 19, 2008 1:14 PM

So you're a tomboy -- big whoop. At try to look like you care about yourself, so other people will think you're worth the effort. Try getting a good haircut, wear a t-shirt that's not 10 sizes too big and not from the bottom of the laundry pile. Mabye even wear something someone could consider "cute."
Sit like a girl, and have good manners. Be open to what comes your way.
If that all seems like too much work, stay home alone with your cat on Friday nights and watch "What Not to Wear."

Posted by Your mother | August 19, 2008 1:20 PM

Aspergers. Just because it needed to be said.

Posted by Bellevue Ave | August 19, 2008 1:21 PM

@2 Yes. I agree. I had a problem with anxiety as soon as I got to college. I'd be lying if I said that the therapy sessions helped a lot, but going through that forced me to look at my problems and get over them.

@9 If she's a nerdy tomboy, she could be striking gold here. There are loads of gamers that are as awkward as she is.

Also: online dating.

Good luck to her!

Posted by Kim | August 19, 2008 1:34 PM

Honey. You can't always get over being shy, but you can put yourself in situations where the shyness is not a factor. My suggestion is to take a class. You could even take one where there are sure to be few women, like welding or brass casting or something like that. Then you have a common experience to break the ice with, joke over, and over the course of the class you can warm up to your new friends, and maybe find someone who appreciates a scrappy tomboy who's good with her hands. Also, shyness doesn't have to hold you back. A lot of people find it sexy! And I agree with Isla above. Masturbate. A lot. You'll figure it out.

Posted by icky | August 19, 2008 1:37 PM

First, about the tomboy thing. Don't worry about it. Plenty of men like tomboys. If being a tomboy means that you are interested in things that are typically male (games of various sorts, nerd pursuits, NASCAR, woodworking, archery, guns, outdoor recreation or something like that) this means that rather than being off-putting, you are instead a valuable treasure. The guys who are into those things want you desperately. They can't find women either, and boy do they want to meet you. All you have to do is go to where they congregate for their activities and they will be all over you.

The only thing I would say you might consider on the tomboy front is your hair. Make sure you don't have a distinctively lesbian haircut (flat-top, mullet or so on.) Short is ok, but there is a difference between short and girly and short and lesbian. This is the main thing that will set off the gaydar you are trying to avoid.

If you have contemplated getting an escort this means you are open to casual sex. If this is so, all you have to do is post an ad on one of the many internet sites saying so. "Shy 26 year old virgin seeks normal man to deflower her. No strings. Relationship only if we click." Let's think about how many responses this ad will receive. There are 6 billion people on Earth. Just over half are women, some of the men are gay or too young, some don't have internet connections. Hmm....carry the three....ah yes, you will get approximately One Billion responses.

Women don't understand this, but all you have to do to get us to have sex with you is ask us. We will. Seriously, any of us. Just don't ask someone with his wife or gym card in hand.

Another thing you should know is that men have the same standards for who they will be friends with as they do for who they will sleep with. I can only think of one woman in my entire life with whom I was friends who I would not have slept with if given the chance. (I am 40 if that gives you any way to gauge how many thousands of women I am talking about). I can guarantee based on your self description that you would not have been one them.

I will now tell you something you will have a hard time accepting, but I absolutely guarantee it is 100% true. You have known or met literally hundreds of men who have masturbated thinking of having sex with you. Hundreds. Probably thousands. Had Dan included your picture with the letter, you would have picked up another couple thousand. As it is, you are certainly up by several dozen. I assure you, men want to sleep with you just as much as you want to sleep with them.

Now, you don't have to hang out in bars to meet men. You do have to leave the house however. If you are actually interested in stuff men are typically more interested in like I mentioned earlier, all you have to do is go to those places. Become a regular. By your fourth visit or so you will have men start to circle around you. Respond to one of them and there you go.

If you are not into one of those manly activities, get into some sort of activity. Go dancing (organized dancing like swing dance, not just dance clubs - it will be easier to fit in naturally for you), Get into some politics committee, join a local chat room that gets together IRL sometimes, or anything else that interests you.

If all else fails, go to church. Those places are full of people looking to hook up. There are more women there than men for that purpose so it is not foolproof, but millions of people meet that way every year.

Posted by Jim | August 19, 2008 1:39 PM

Good advice, Dan.

The other thing is to make the first move - it doesn't have to be a lot, just brushing someone's arm or saying "oh, did you want to buy me a drink?" when you're talking with someone attractive.

Posted by Will in Seattle | August 19, 2008 1:47 PM

If you're with a guy and don't feel confident, he's going to read that as your not being into him/the situation. So say stuff that makes him feel like you DO want it to continue. "I'm so turned on by you" or "Wow, you are a great kisser. Can I have another?" Use your brain and mouth to overcome the bad body language you're giving off because you lack confidence to convince him you want him to keep going.

Posted by Yo there | August 19, 2008 1:49 PM

Life is too hard and complicated for you, TOBS: Advice .

Posted by Mr. Poe | August 19, 2008 1:49 PM

I'm touched by your story. I feel much the same way.

Lust was designed to overcome our inhibitions, otherwise the human race would probably have died out long ago. Izla @ 13 is right, cultivate your horniness and leap in with your legs spread.

Yes, the hard part is the sense of not being wanted which will overpower even the best sex. That's the conversation you will be taking up with yourself. Here is some advice from Rainier Maria Rilke which I've found helpful:

...Let everything happen to you, beauty and terror
Just keep going
No feeling is final...

take care

Posted by John | August 19, 2008 1:52 PM

@ 18, Jim scared me. Relax, thousands of men jack off about you? Soothing stuff.

Posted by robo | August 19, 2008 2:01 PM

I'm a straight guy. I had no confidence with women my whole life. I was a virgin until 21. I went to bars and drank heavily to overcome my lack of confidence for years. Finally, when I was 28 I decided I had enough. Confidence or no confidence, I decided any time I met an available woman I was attracted to, I would ask her out. I was shot down a lot, went on a lot of first dates that went nowhere, had a couple of relationships that lasted a month or two and then about a year into it met a woman who would become my fiancee six months later, my wife 6 months after that and I'm still married to her 9 years later. And to echo Dan's advice: I don't go to bars anymore. I went to meet someone, I met her and I'm done. My advice: at no time during this process did I ever have confidence, but I sure pretended like I did.

(Oh, and she should learn to give a really good blowjob.)

Posted by fribster | August 19, 2008 2:09 PM

If simple advice was going to help you it already would have worked. This level of shyness is most effectively addressed with a therapist. Cognitive Behavioral Therapy for a quick (but not necessarily permanent) fix. Insight based therapy if you want to get to the bottom of it and have the will to do so. Medication might be very beneficial. I've seen it work with people who have this issue (yes there are others) very quickly. Finally, exercise, especially of the team sort, might help teach you to interact with others utilizing your body without actually having to talk about much of anything. The confidence you develop might transfer over and at the very least will put you out there.

Posted by LMSW | August 19, 2008 2:13 PM

I hope this doesn't sound like too much of an ad(and I have no connection beyond being a user. 'sides, it's free.), but try You answer a bunch of multiple choice questions, then see who in your area you have a high match percentage with. I would be willing to bet that at least half of them would find you interesting.

Most dating sites focus first on the picture, then on the profile, or focus on unimportant traits rather than preferences. You have to slog through tons of profiles, just to find one person even remotely interesting to you. That really IS the meat-market approach. So don't give up just because the dating site you tried happened to suck.

Posted by Clay | August 19, 2008 2:17 PM

I was like her when I was 26. Not quite a virgin, but close enough. It lasted until after 30, actually, and I can instantly summon up that pain.

Confidence comes from not trying too hard, I think. People can smell the desperation on her. She needs to take the advice above -- not necessarily bars, but OUT IN PUBLIC -- classes, activities, hanging around parks and art galleries or bookstores or whatever the hell -- but first she needs to convince herself "today doesn't matter; I am comfortable with who I am and not dependent on anyone else". Then, when she meets people -- and she will, she's probably meeting a dozen people every day and doesn't realize it -- she'll be able to communicate with them from a calm, level plane. The goal is not "get laid right now", it's "have a conversation with a potential partner, if that's what we decide we'd like to try". Once you're relating to people evenly, the next steps can follow.

One thing about the ads is that there might seem to be some pressure there, which might be hurting her style a little. But again: don't think of every person who calls as "this might be the one"; think instead "let's hang out with this person for an hour and see how we get along".

And PLEASE set your mind at ease, darlin'. There are MILLIONS of guys out there who go bonkers for tomboys. It's not all about the giant inflatable boobs, really it isn't.

Posted by Fnarf | August 19, 2008 2:20 PM

i used to be a lot like you, as you describe yourself. went to a single sex high school and didn't do anything but study. then went to college with the dating experience of a 12 year old (ie, none). the things that worked for me?

1. online dating. my first few dates were all guys i met online, as was my first serious boyfriend. after first having dates with guys i met online, finding out they didn't scream and run in horror at the sight of me even if there were no repeat dates, and then progressing to a long term boyfriend, showed me that yes, i am dateable. hooking up with guys i met online after first boyfriend dumped me showed me that yes, i'm fuckable too.

2. getting drunk, going to parties in college, and hooking up. i don't know about you, but when i'm drunk, my shyness and inhibitions go away and i'm close to a normal person in terms of willingness to talk to strangers/hit on people. seriously, start drinking until your inhibitions go away, talk to some guys, and then grab one and start making out with him. i highly doubt he'll mind (unless gay, of course).

Posted by shy lush | August 19, 2008 2:22 PM

Join a coed softball/volleyball/bowling team. Join it with a girlfriend if you need moral support. The casual interaction with guys will make you feel comfortable and build your confidence. Plus there will be many occasions to laugh -- just don't join one that's hyperserious about winning. Teams usually end the evening by going out for pizza and beer -- another way to get comfortable.

Let the guy make the moves, but let him know if they're making you uncomfortable.

Posted by take it slow | August 19, 2008 2:26 PM

In your situation you just can't afford to get squeamish about internet dating. It is a great way meet people and make mistakes in a fairly anonymous setting. Hitting on people in person is much more difficult and requires a healthy dose a self confidence that you don't seem to have yet. Plus EVERYONE is doing it. I know many people who have had great sex/relationship luck in the past but are still turning to online dating because it simply works better for them than lurking around bars all the time.

I used to be painfully shy as well, and I learned that you just can't wait for shyness to go away on its own (it won't). Getting some experience (and this applies for all of life) is really the only way to start changing how you feel about yourself. Now stop whining and go!

Posted by Ashley | August 19, 2008 2:48 PM

Until you're happy with yourself nobody else will be. Try masturbation.

Posted by Vince | August 19, 2008 3:03 PM

Oh, jesus christ, 24. Her problem is that she can't get near a dick, and you want to make her nervous about not knowing what to do with it?

You can't learn on a popsicle. You've got to have a guy responding to what you're doing.

There's good advice here. I think the best is just to set out to have a brutal couple of months -- approach everyone you're the least bit interested in. Don't go in assuming they won't want you, that will lead to your lack of confidence making them uncomfortable, but be prepared for them not to want you, and not to care. It's a couple of months of expressing YOUR interest, without undue regard for their reciprocity or not. Don't take the refusals personally. This is a learning exercise, that's all it is. You're learning that you expressing want, and someone else saying no thank you, does not have any real impact on who you are, and how your life goes. It's survivable. Somewhere in this, you'll get responses, and then you can move on to evaluating the responders.

And it can't be emphasized enough -- you can't get what you want if you don't dare move out of your comfort zone. I feel your pain, but you've got to. Classes, personals, sports -- you want a big pool to swim in.

Posted by Terry | August 19, 2008 3:05 PM

Men are way more nervous of you than you are of them.
Think about it - our culture tells them both that they have to make all the moves (several commenters above allude to "letting him make the moves), but also that if they make any moves in the wrong situation, they are sexist assholes.

Easiest way to get laid: ask. If rebuffed, ask just one more time (I'm serious about that; sometimes guys feel like they need to be Extra Respectful of your Virtue, but if you say, "I'm not sure you understand - I REALLY want YOU to fuck me," you tend to get good result).

Also, don't fuss about being a tomboy. How many guys out there have fantasies about being with dykes? And then there you are, outwardly a lot like a dyke, except totally hot for dudes.

Anyways, the thing is - it's this massive psychological barrier. If you've never had sex, it's easy to become convinced that there's some huge hurdle to get over and you don't know how.
But what is probably happening is that on some level, you haven't actually wanted to have sex. I know that happened to me; I was sort of vaguely discontented until I was 21, thinking that there was something wrong with me because I had never been in a serious relationship or had sex.
But then some things changed, and I realized that I actually hadn't been trying, at all. And as soon as I actually tried (you know, left the house, pursued men/did not evade pursuit, and was willing to actually go home with them if the pursuit worked rather than finding an excuse to bail), it happened.

So my more succinct advice to you is, if you really want it, go get it. If you don't really want it yet, that's okay too.

Posted by Sailor | August 19, 2008 3:48 PM

So Jim@18, everything he says is spot on.
Same with fnarf@27, actually. They just are emphasizing different points. Listen to both those guys.

All the recommendations people are making about alcohol, I dunno. It works for a lot of people, sure, but not everybody. Ask yourself if you have more fun talking to people when you (and they) are a little buzzed. If the answer is no, it may not be the way to go.

Posted by Eric in Boulder | August 19, 2008 5:14 PM

I am a tomboy, and have been mistaken for a lesbian. I am also a sci-fi nerd. I made friends with guys with much more ease than I dated, resulting in endless crushes and frustration. You need to be comfortable with yourself before anyone else will be comfortable with you.

How to do that? Well, I ended up in a place where men outnumbered the women by a fairly large margin (the military), and you know what? Not all of them were interested in me, but there were plenty that were, and that experience really helped the low self-esteem/depression/whatever that came with not being the prom queen girly girl I thought all guys wanted.

Whatever your type, there are guys out there who are attracted to it. Get comfortable in your own skin, enough so that you aren't putting out a desperate vibe, and put yourself in situations where men can notice you being you, and being happy with yourself.

Posted by RJ | August 19, 2008 6:02 PM

Perhaps her problem is not the lack of sex and dating but the desire to date and have sex. Focusing on having a fulfilling life without a man would probably be more... fulfilling.

Posted by Just a thought | August 19, 2008 6:43 PM

@33. I endorse this product or service.

Seriously, everything she says is correct. The business about asking twice is especial genius and an insight I would have thought you would have to be male to have.

Guys are terrified of women. We also (especially the less experienced among us) really want to be sure you mean what you say. Guys will turn you down the first time because they think that either what they are hearing is too good to be true and is some sort of trick, or is a test that they can only pass by turning you down. If you ask again, their fears will be laid to rest, and something else will be laid as well.

When I was a teenager, I was in a girl's dorm room. The door was shut, and she told me "I don't think it is necessary to be in love with someone to have sex with them. I can just have sex with friends as well." I was quite attracted to this woman. My reaction? Freeze, wonder whether I fit that category, and hope she would elaborate more on this wonderful theme.

I did not get laid that night. From my perspective, I just wished she could be a little more clear in her intentions. From her perspective she got up right in my face and yelled "HEY, WANNA FUCK?????" I was left wishing I could have gotten some and wondering what I should have done, she was left thinking I had rejected her.

Posted by Jim | August 19, 2008 7:23 PM

This was me. I didn't have sex until I was 29 - I didn't even make out until I was 29, and I was the same as her with the tomboy/everybody-thinks-I'm-gay thing.

How I broke the jinx: I just had casual sex with a guy who was cute enough but I didn't respect him enough to have a crush on. I barely knew him. He hit on me [all those articles of clothing my brother told me boys wouldn't like, this fella cited - unasked - as things he thought were just so cute]. I didn't care what he thought, and just told him the deal straight up with the lack of experience. He was fine and dandy with that, and we even did this thing that was like a variation on the Antioch Rules, where he'd go "can I xyz?" and I'd say yes or no, and if I said no he'd ask if he could do something lower level until I said yes. And sometimes I'd offer, "you can now do abc..." or whatever. It was funny and fun. We were grinning the whole time. Then when the ice was broken we kind of went to town all summer. Also, there was an understanding this would be strictly a fling. He later tried to ratchet that up, but I politely declined. And after that I was self-confident enough to join the human race, get a boyfriend and a broken heart, all without any stigma about the inexperience.

Nutshell: low stakes!

Posted by Anonymous Female | August 19, 2008 7:43 PM

I'm sure you're not reading the comments on this, but seriously, I'd love the chance to go on a date with you. It's not a creepy obsession over the have/haven't been laid in x number of period y, it's that you sound like someone I want to meet and know more about. You're the type of person I want to respond to the personal ad, but you never do. :(

Posted by Where have you been all my life? | August 19, 2008 7:59 PM

Ok, I just read everyone else's advice and can heartily endorse Jim @18. The guy who hit on me [story at #38] I met volunteering at a cable access show. In other words, I was my geeky self, and somebody liked it. I'm not going to lie - it helped that he was ridiculously forward, because I was as shy as you are, but it really helped that I didn't have to pretend to be somebody I wasn't in order to attract a consenting adult. I very much think you don't have to, either. Everything Jim says is true. I am much older now and I know it.

But again - it very much helped that I didn't have a crush on him and didn't much care what he thought. This might be key, in fact.

Posted by Anonymous Female | August 19, 2008 8:01 PM

Girl, you are the reason the saying "fake it till you make it" came into being. The next time the opportunity presents itself, do NOT tell the guy you are a virgin, or any of your other insecurities and stuff. Just act like you know what you are doing, and let the moment happen. You are scaring the guy's off telling them I'm a virgin and I'm so new to this and I might screw it up and AHHHHHHHH!!!!!!!!!!! Then they run before you even get going. Just go with the flow, act like you know what you are doing, and let the sex happen. It probably won't be great, your first time, but then you'll have it over with and the next time you'll know a little more what to do and it will be better and so on. But you've got to let it happen and just get that first time under your belt.

Posted by ferretrick | August 19, 2008 8:42 PM

27 year old male virgin in similar boat. i feel her pain. if i wasnt about to head off to china (where i hope my exoticness will get me laid) i'd email dan asking for a hookup

Posted by fdsa | August 19, 2008 8:56 PM

I think letting lots of people respond to this letter is going to be counterproductive for this person.

You're clearly over-thinking things. Reading more than 40 responses probably isn't going to help you.

"I'm starting to feel like it's unfair to lay all that at the feet of any guy" You're right, and it isn't, and he doesn't care. All he wants laid at his feet is you naked. He doesn't want your baggage or your insecurities, he wants to bang you. Guys probably come on to you all the time and you don't even notice. You are expecting them to have some kind of discussion with you, they're just saying "hello" which means, "please smile and appear receptive so I know there's some chance I'll get to nail you."

Stop expecting that these guys are considering any of the stuff you wrote about, or that they care about it. They don't. Realize that most guys are walking penis's and if you can spend one night pretending you don't have these problems, the next morning will wake up, search for your clothes, sneak out of his apartment without waking him, then all of these problems will have disappear in the morning sunlight and you'll be able to move on and meet a guy who will care about you, and you will not have to burden him with this crap because it will be gone.

Posted by Fierinferno | August 19, 2008 10:26 PM

One thought about reducing the anxiety about meeting people: don't think of the people you're meeting now as potential dates/fuckbuddies/whatever, but rather as the people who will later on be introducing you to their cool friends. Get out there and meet people who have interesting friends and proceed from that point. Looking back on my own relationships, this is pretty much how all but 1 got started.

Posted by Monsieur le Fer | August 19, 2008 10:32 PM

@ 42:

Fdsa, sir, I don't care if you weigh four hundred pounds and have hideous facial scars. If you somehow fail to get laid in China, I will eat my hat. I live in China, had similar issues to the girl who wrote the letter, and it was easy getting some tail as soon as I got over here.

Perhaps that's not a bad idea for the tomboy in question. You know, there's a terrible gender imbalance over here, and Chinese dudes really go for foreign girls...

Posted by Another Dan | August 20, 2008 4:08 AM

I am a geeky girl who found my husband by going to an engineering school where the male/female ratio was 4/1. You say that you don't like bars, but you don't say what you do like. If you are interested in any kind of activity that can get you in with geeky males, I think you'll have good luck. Think Dungeons & Dragons, sci-fi conventions, computer programming groups, ham radio. You do sound a bit asperger-y and aspies usually have some kind of geeky obsession.

One other issue: might you be using the lesbian identification as an excuse? When I was in college I used to not study even if I had time. Then if I did bad on the test I could say to myself "well it's just because I didn't study". Looking back, I think I worried that if I studied and then did bad, I would feel like I was just stupid, which would be quite horrifying. Maybe you are dressing/acting like a lesbian so you can protect yourself by saying "well, it's just because people think I'm gay that I can't get a date, not because there's anything wrong with me." And of course there probably is no big underlying reason you can't get a date. You just need to let yourself be a little vulnerable and accept the fact that in finding a great relationship you will be hurt and rejected along the way.

Posted by snoozn | August 20, 2008 8:02 AM

I have the utmost compassion for you. I was the opposite: precociously confidant sexually, before I could handle, it b/c I was sexualized very young, resulting in an about face in young adulthood. As an adult you can learn to express this part of yourself at your own pace in a safe relationship. I'm sorry it's taking you so long to work your way to it. I would recommend putting an ad up in the activities section of craigslist or some other community message board. Look for new friends to do ACTIVITIES with, get to know new people, male or female, to flex that muscle, and in the process you may find someone you click with who gradually becomes something more. Lose the anxiety, it's hurting you and it isn't serving you in any way. You CAN get over it. Just keep flexing your social muscles by putting yourself in comfortable situations with new people (safe, people whom you've vetted somewhat.) Try finding companions for something you love to do: ultimate frisbee? Going to museums? Flea Markets? Good luck and may the force be with you!

Posted by FC | August 20, 2008 8:26 AM

Dan, send her my way. I can relate to a lot of the things she is feeling and I think I can probably help her out.

Also, I can score a cute tomboy chick in the process. It is a win-win situ.

Posted by Ryan | August 20, 2008 9:59 AM

What *do* you like? Sounds like you're using the "lack of experience" as a euphemism for your painful shyness and social awkwardness.

Try something new: take up mountain biking. Seriously. There's like one female tomboy with no social skills for every 100 mountain bikers out there. Start going to races. You'll get in shape, and you'll find loads of opportunities for meaningless cheap sexual experiences. Good luck!

Posted by ibc | August 20, 2008 1:13 PM

There's nothing physically wrong with me. I'm incredibly shy have no confidence and can't seem to do anything about anything unless it's an immediate problem

Posted by fdsa | August 20, 2008 7:27 PM

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