The trouble with me...

November 10, 2008 7:52 AM

Two frustrating issues about me that keep coming up, in the context of dating/relationships. (sex talk, so maybe NSFW)

So I've been dating this girl for about a month, and she's raised two issues about me. These two issues have come up with regularity in past relationships, and I'm at wits end trying to deal with them, mainly because I feel I can't control these things.

1 - Compatibility: "I'm not sure I'm right for you. I do like you but not in exactly the same way (I don't think). Know that there ARE feelings there, I'm just not sure what they are yet."

I don't know, it's like I can't find anyone that is remotely like me, so I've developed this psycho-defense that goes like this: any two mature people can have a relationship, it's not about some abstract notion of compatibility. I'm almost certainly wrong about this, but tell me why? how? Who am I supposed to date? How do I know who to look for? Where do I find girls who are like me?

I know I know, just do the things you like to do, right? But I'm an introvert! I read and write in my spare time. I do a lot of things by myself, and I'm really comfortable with that. But I want intimacy, it's calming and comforting just to have someone of the opposite sex that I can touch and will touch back. So I go on okcupid or something and compromise all of my interests so that I actually get some results, and I date whoever, and so far it has been a really mixed bag (sorority girl, super-christian girl, soccer player girl, bohemian girl, single mom, much older, etc. etc.), but not any of them have stuck. I almost always feel I become their "pet", their pseudo-virgin, over-intelligent, over-thinking, wisdom seeking, hippyish, frugal, techie, geeky little pet that they get tired of after a while.

Where do I find pseudo-virgin, over-intelligent, over-thinking, wisdom seeking, hippyish, frugal, techie, geeky girls?

2 - Sex: "The sex... I'm glad you liked it. That was the point... it wasn't as satisfactory for me."

When the hell did everyone go and become sex masters? Seriously. What can I do about this? Do I have to pay a prostitute to work up experience? Arghhhhh.

I have had sex a total of less than 10 times. I get really nervous about sex, it scares me in a way. But at the same time I really do desire it. I have a tendency to take longer than the girl does to get off (due to the nervousness), and sometimes I can't even finish. Another thing is I never feel as if I can get into a good hip movement rythym. Compared to masturbation, sex is hard, and it doesn't even feel as good (not as much friction, makes it harder to get off too). I would almost rather just sleep with the girl than have sex, just because it's a more steady intimate feeling, and there aren't any "standards" or expectations for that. I've never had sex with a girl more than once, things always seem to end right after or soon after our first time. Am I really that bad at it?

I'm not necessarily looking for answers to any of these questions per se (although that's fine), I'm looking more for general situational advice.

posted by symbollocks to human relations (33 comments total)

I've never had sex with a girl more than once, things always seem to end right after or soon after our first time. Am I really that bad at it?

I would say it's not a matter of your being bad at it -- I'd say it's about 40% you getting anxious to the point that you're second-guessing yourself all over the place and tying yourself in knots. But -- it's also 60% you having dated INCREDIBLY selfish women.

If your only sexual experiences have been with women who slept with you once, and then said to your face "hmmmm...you know, that maybe wasn't so great, see ya," then either they have unrealistic expectations and they're not cutting you some slack or you're all having sex way too soon. Any woman worth her salt knows that the first time having sex with ANYONE is rarely transcendant -- you don't know what makes each other tick, it's a fumbly sort of affair because you don't know how all the gears mesh. It's DOOMED to not be that great.

But the women who are actually into you as a person will forgive this and take it in stride rather than breaking up with you just because the sex wasn't great. The only women who DO do that were never into you as a person anyway, they just wanted to get off. They're expecting perfection from the get-go, and ignoring the person.

You don't want to be with women like this. Just like I don't want to be with men like this.

But I'd also say that you've also been working yourself up into such a state of anxiety about this that it's hobbling you. Let me ask -- how soon do you start sleeping with someone? First date? Third? Maybe waiting longer and getting to know the person better would help -- it would weed out the women who are treating you like a piece of meat.
posted by EmpressCallipygos at 8:04 AM on November 10, 2008

Am I really that bad at it?

I seriously doubt it. It just takes more practice, with one person that you're comfortable with. Once you get a chance to experiment with someone and get to understand what you like and what they like, it gets much better, and that translates to future partners, too.
posted by cabingirl at 8:29 AM on November 10, 2008

1 - Compatibility: "I'm not sure I'm right for you. I do like you but not in exactly the same way (I don't think). Know that there ARE feelings there, I'm just not sure what they are yet."

sounds like you're getting one-night standed. if she's not interested in a real relationship, there's not much you can do about that. it's a shame if you've never been in one, but i wouldn't worry about that. try dating a different type of girl (or guy - you never know).

2 - Sex: "The sex... I'm glad you liked it. That was the point... it wasn't as satisfactory for me."

so put the chick on top. you don't put a student driver in NASCAR and expect a decent performance. she wants it her way, let her drive for a while.

I have a tendency to take longer than the girl does to get off

many would not consider this a bad thing.

Any woman worth her salt knows that the first time having sex with ANYONE is rarely transcendant -- you don't know what makes each other tick, it's a fumbly sort of affair because you don't know how all the gears mesh. It's DOOMED to not be that great.

oh! but on TV they have glorious, ineffible, golden orgasms at first touch and fuck like bunnies all night long! you mean that doesn't happen in real life?
posted by mr_book at 8:31 AM on November 10, 2008

Where do I find pseudo-virgin, over-intelligent, over-thinking, wisdom seeking, hippyish, frugal, techie, geeky girls?

I don't know what a pseudo-virgin is, or why you would want to find one if you haven't had a lot of sexual experience. Finding someone experienced, but patient (someone to show you the ropes, so to speak) might be a better idea.

Generally, I think your desires for a woman who's just like you (I mean, really, frugal?) are a little silly. Instead, focus on someone you have fun having conversations with. I guarantee that the sex will feel more comfortable if you can talk to a person generally.

But I'd also say that you've also been working yourself up into such a state of anxiety about this that it's hobbling you. Let me ask -- how soon do you start sleeping with someone? First date? Third? Maybe waiting longer and getting to know the person better would help -- it would weed out the women who are treating you like a piece of meat.

I think this is excellent advice, and second it.

Compared to masturbation, sex is hard, and it doesn't even feel as good (not as much friction, makes it harder to get off too).

Try masturbating with lube to get used to the sensations of sex. Also, stop defining sex as coitus--it can encompass a whole range of sexual acts. Cunnilingus, for example, does wonders for satisfying women.
posted by PhoBWanKenobi at 8:32 AM on November 10, 2008

Where do I find pseudo-virgin, over-intelligent, over-thinking, wisdom seeking, hippyish, frugal, techie, geeky girls?

1. MetaFilter, seriously. I have had the same feelings that you describe when I'm looking at an online dating site and thinking "geez, if I describe myself accurately, I am going to be appealing to exactly no one" which may (or may not) be true of Nerve.com but is definitely not true at, say, a MetaFilter meetup which is, incidentally, where I met my current squeeze. So, I totally synpathize with you being an introvert and yet wanting affection. And, at the same time, maybe you need to sort of hang out online without necessarily doing a dating-specific activity online. Granted it's much easier to be in this sort of situation as a female since we're underrepresented in geeky online places generally but sometimes putting yourself out there a little [indicating that you're single and straight, for example, in any social sites you happen to frequent] is a nice and simple way to hang out the "available" sign without the myriad of checkboxes that is online dating.

Again, none of the interests you are describing seem offputting at all to me personally. If I were twenty years younger, you would be my target guy.

2. Those women are rude. If you're having sex and your partner is getting off, you're already head and shoulders above a lot of the early-20's guys I fooled around with. That said, that's not helpful. Communication is generally the key to good sex but for more cerebral types, especially anxious ones, this can be not the simplest advice. Again though, you not being a total horndog works in your favor with at least some women, so I wouldn't look at this as a failing, I'd look at this as a bad fit so far and go looking for a good fit.

This is not to say that a good sex partner will automagically be able to establish a perfect sex rhythm with you and all will be wonderful but that a good partner will be understanding and responsive and you can both work on your sex thing and make it better together. Generally speaking sex doesn't exist except as the product of two people doing it together so while it's too bad that you haven't clicked with your current partners, I don't think [at all] that it means you are bad at anything, just that the chemistry/physics were bad.

So, think about sexytime things that maybe aren't the old in-and-out if you feel that your hips don't do what you want them to, or see about positions where it's not all about you and your hips [her on top, mutual masturbation, 69, whatever]. Also attitude matters at least a little. Your anxiety may be palpable and may put a damper on what should otherwise be fun and playful times so see what you can do to get yourself at least a little outside your own head so that you're not just overthinking yourself out of a good time.

Also, I can't stress enough, for a lot of geeky girls who may also be a little awkward or twitchy about sex, saying "hey do you want to just play video games and snuggle?" can be very hot indeed, plus one of the best ways to have hot non-overthinking sex is to wake up in the middle of the night in bed with someone....
posted by jessamyn at 8:33 AM on November 10, 2008 [4 favorites]

You sound kind of down on yourself, which is too bad. I don't think there's anything you're doing wrong, you just haven't found the right person yet. You sound like a great, perfectly datable guy, and I think the sex you want will follow from having a mutually caring relationship with the right person, so I wouldn't worry too much about that right now (easier said than done, I know...)

As for advice, I think you need to meet people in person - online dating obviously isn't working for you. You say you like to do things alone, but can you do them alone ... in public? Doing your reading or writing at a library or coffee shop lets you start to build rapport with other regulars. Are you anywhere near a university? If students are in your age range, I bet there are lots of intellectual upperclassmen or grad students who could be perfect you. Is there anything you have a passing interest in where you could join a club, go to events, etc (I'm thinking things like chess, community education classes or seminars, music and concerts...)
posted by robinpME at 8:36 AM on November 10, 2008

I've been formulating an ask.me question of my own that's similar to your #1 point, so I'm curious to see the answers here. Still, I'll take a crack at it:

You say you've developed the viewpoint that compatibility doesn't matter... a viewpoint that you yourself are suspicious of. You then proceed to date women who you are not particularly compatible with and then wonder why they say that you're lovely but just aren't right for you.

Do you see where I'm going with this? They aren't compatible with you, but you're willing to squash your whole personality to be with them. Putting aside the face-value incompatibility, by squashing your own personality, you're placing yourself in a submissive, subservient position. And then they treat you accordingly.

There is a fine balance required for us introverted, nerdy types. We have to fight our anti-social tendencies if we ever want to make true connections. But we also must develop our better, more interesting parts of our personalities if we want to be loved for who we are, not just how well we can contort ourselves to the needs of someone else.
posted by specialfriend at 8:38 AM on November 10, 2008 [1 favorite]

it's like I can't find anyone that is remotely like me, so I've developed this psycho-defense that goes like this: any two mature people can have a relationship, it's not about some abstract notion of compatibility. I'm almost certainly wrong about this, but tell me why?

Because people don't want to have a relationship with just anyone; that's not fulfilling. They want to have a relationship with someone who they're enthusiastic about, who they actively want to spend time with... not someone that's a chore to spend time with.

That means they need compatible personalities. Note that compatible doesn't mean "exactly the same" -- there are some outwardly opposite people who have great relationships with each other. It just means they have to mesh well enough that they are happy spending time with them. My husband, for example, is an introvert, and we agree on pretty much everything politically and have similar interests in a lot of areas, but he's more of a math/science geek whereas I'm a literary geek. We're both receptive to learning about those things once the other has distilled the basics of something for us, but it's not something we're inclined to check out otherwise. I'm more outwardly emotional and if I didn't know him better, I'd probably think he was aloof. It works well in practice. You have to be careful you don't look for something too specific; considering that I'm so opinionated about literary things, I think I would be miserable dating a fellow literary geek. It's really less about hobbies than it is about personalities; they can be completely uninterested in your favorite hobby and it might not be important in practice.

You just need someone who is your complement, where you both enjoy spending time with each other. There's nothing wrong with striking out a lot along the way. It's harder for introverts to find someone they want to spend time with, I think. It takes a lot to find another person whom you could actually have more fun with than you could by yourself. The sooner you accept that instead of fighting it, the better. If you go in thinking it should be easier than this, why isn't it working, you're just going to be disappointed. You're not an extrovert who has a wider range of people they're happy being around, and that's the breaks. It's not insurmountable, just deal with it.

But I'm an introvert! I read and write in my spare time. I do a lot of things by myself, and I'm really comfortable with that. How do I know who to look for? Where do I find girls who are like me?

Me too. I'm not sure if this is going to be comforting or depressing, but I've never had trouble finding prospective relationships; I've had to turn down offers again and again while I was dating, and now I'm married.

How would you rate your social skills? Even introverts have to have them. If you rate them poorly, that's the first step.

First, you have to make the effort to meet people. This will be less agonizing if you go to something you would enjoy regardless of whether you meet someone there; I know I don't like going to anything for the sake of meeting people and will skip it unless there's another compelling reason to go. This will also be easier if you're still in school, since there are more opportunities for events like that.

Second, make sure you're going places where the type of girl you describe might hang out. As a girl who fits a lot of the criteria you listed, I can say with some authority that you'd be very unlikely to find her at a club, for example. It could happen, but it would be a disappointing use of time on the whole. Go places that involve things you enjoy, and you can know that other people there enjoy the same thing.

Failing those first two things, there's nothing wrong with using online dating services and putting a lot of what you wrote here, there. For example, I love reading and writing, but joining a book club or writer's club or anything like that makes me cringe; it's not something I want to do in a group. When your interests are largely things you prefer to do alone, online dating is one of your best options. I think the reason you've had problems is because you've "compromised all your interests" on okcupid. Of course if you do that you're going to get crappy results. You seem to want quality over quantity, so why are you setting yourself up for the opposite? Be honest on your profile and be glad you don't get bad matches. If it takes months to get a good match, so be it. You don't get any special medals for having the most number of failed relationships. It doesn't matter if you get a lot of responses if they all suck.

There's another thing you should be sure to do in the meantime. Most of the times I've been asked out, it was by friends or friends-of-friends. My introvert husband started out as a friend from school. Hopefully you have friends that share some personality traits or interests with you. They might know other people who share some of those as well, and those people might be "compatible" with you. Your geeky friends might know other geeky people you don't yet know, for example. That's a lot easier than trying to navigate a sea of strangers. That means when they say, "Hey, wanna go do Activity with Person You've Never Met Before?" you might actually say yes. As a fellow introvert, I suspect you turn those offers down; mixing groups of friends can turn out awkwardly, and it seems easier to just avoid it. Learning to accept invitations anyway is valuable.

As for sex... right now, focus on finding someone whom you're excited about who is also excited about you. Yes, someone you're "compatible" with. If they don't feel compatible with you, the sex isn't going to be that great for them, so don't be so hard on yourself just yet. Plus, if you find someone who's really into you, they're going to be more willing to make you feel at ease and work through your nervousness. That's nothing unusual. If you get a good relationship going and still have problems, then post about that specifically. I doubt your partners are sex masters. Right now, it sounds more like "Unenthusiastic Couple has Mediocre Sex: Film at 11." Unsurprising.

Aside from that, though, most guys find it easier to come faster when they haven't masturbated in a while. I think this is especially worth exploring in your circumstance since you feel masturbation is easier than sex. I'm not saying you're wrong, just that it may relieve some anxiety if you stop masturbating a bit and then find it easier than expected to come next time you have sex.
posted by Nattie at 8:49 AM on November 10, 2008 [1 favorite]

it's also 60% you having dated INCREDIBLY selfish women.

He'd be better at sex if he had. No quicker way to improve than on-the-job training from someone who just wants to get off. Try making her teach you.
posted by bonaldi at 8:57 AM on November 10, 2008 [1 favorite]

1) Quit compromising your interests and you'll find a girl who likes you.
2) Quit masturbating (so much). It seems to be getting in the way.
posted by rhizome at 9:23 AM on November 10, 2008

I could have written this myself 3 years ago.

I haven't fixed the relationship part, but the sex part, I realize, is as much their problem as it is mine. I've gotten together with several women in the last 2 years who could really appreciate (worship) the fact that it takes me a long to get off. It's not nerves, it's just the way it is. Anyway, it's no longer a problem. I had a girlfriend for a while who was into sex for about 2 minutes worth, and would be annoyed that I'd want to go (significantly) longer. She was a nice girl but made me feel really weird about that.

Then I had a sort of one night stand with a woman who was so psyched about the same characteristic. She said what I still consider to be the nicest thing that anyone has ever said to me, "you ruined me for all other penises". I mentioned my previous girlfriend to her and she was incredulous.

Then I had a friends with benefits situation with someone else that matched me sexually (not intellectually at all, which is sad and a whole other story). But we had lots of great sex over a few months.

It's weird, I went from being pretty weirded out about sex to feeling totally comfortable and confident about it in about a year. Mostly due to that one night stand.


Getting sex in the first place, and moreso, the relationship I desire, that's still going pretty awful. I don't have much advise for you there...
posted by sully75 at 9:38 AM on November 10, 2008

1. "Where do I find pseudo-virgin, over-intelligent, over-thinking, wisdom seeking, hippyish, frugal, techie, geeky girls?"

In my experience? Cons. Sci-fi, fannish, general spec fic, gaming, anime, even serious flat media cons.

If you feel like you can filter out the scammers and pros, there's also Craigslist...but that goes more to your second question.

2. You've already figured this out, but, yeah, sex takes time and experience to really get the most out of it. Since many other people are starting out earlier and earlier, they've just had more experience by the point you're meeting them at *and* they're probably not having to deal with the issues caused by over-analysis.

I don't think you need to go so far as to hire a prostitute. I also don't think you need to (or should) skew your interests in the matching services, since that presents a facade that's never going to really match up to who you are in real life and will generally lead to ultimate disappointment until you get insanely lucky and meet the girl of your dreams who happened to also skew her results and...well, it's more likely to happen in the movies, is all I'm saying.

At those cons I mentioned above, you can meet people who may be in the same situation you are - not a lot of experience, wanting to get it without being judged, not necessarily knowing what you want to commit to yet...I'm not saying that cons are like geek meat markets, but maybe there's a little bit of that at a number of them. I just think they might work as a safe place to meet people of a similar bend and see where that leads.

Being up front with whomever you get a chance to consider intimacy with and seeing if they're interested in taking an actively instructive role during at least the first few times might have a better pay-off than you think - just know that you'll be learning what that woman likes, which may or may not translate to the next woman.

You could also use the premise of just learning how to be better lovers together and remove the layer of responsibility from your partner, like asking to try techniques from various books and other sources. Even watching other people doing things and trying those with your partner could lead to better experiences for both of you (as long as you pick something to watch that meets each of your sensibilities, of course).

Books like "The Intimate Couple" and "The Joy of Sex" make it easy to read through on your own and then bring up the things that interest you most or seem helpful to your partner.

The best thing to keep in mind, regardless of what you choose to do, is that sex is like dancing - the more you learn how to do it without caring about outcome or what other people think, the better it gets.
posted by batmonkey at 9:45 AM on November 10, 2008

When the hell did everyone go and become sex masters? Seriously. What can I do about this? Do I have to pay a prostitute to work up experience? Arghhhhh.

Okay. Stop. Breathe.

It sounds like most of this is being built up in your head. Take your time and don't expect everything to work perfectly the first (3rd or 12th) time. You mention your partner is satisfied and you are not. I think you've gotten too used to your own hand, and possibly way too tight of a grip. When you start seeing someone, try to take a break masturbating. Build up the desire so being with the other person will be the release you need. With the rhythm issue, let her take over. Have her be on top, see how she moves. Something may click, physically or mentally, and this will probably be a lot less intimidating as a whole.

If you still can't finish, explain it. Don't be overly apologetic, just say something to the effect of, "This all feels really great, but I don't think I'm going to get there tonight." Make sure it felt good for her, take a break, try again later. It's not a contest, orgasms are not required 100% of the time.
posted by piratebowling at 9:52 AM on November 10, 2008

In my experience? Cons. Sci-fi, fannish, general specific, gaming, anime, even serious flat media cons.

But I'm not into that scene? I'm not really into any scene, and I can't really make myself be interested in those things purely to meet people, or can I? should I?

I'm feeling sort of trapped between two worlds: academia and the working poor.

I don't go to school, but I'm very focused on learning. I don't like the expensiveness, beauracracy, or career focused attitudes of the university.

I work, and I don't make a lot of money, and I like it that way. But there aren't a lot of people that like to learn or are interested in anything besides "making it" among the working poor because so many of them are constantly in crunch mode, barely making it in tough shitty jobs. All they can think about is vegging out in front of the TV for a few hours before bed.

Where do these worlds collide?
posted by symbollocks at 10:10 AM on November 10, 2008

Where do I find pseudo-virgin, over-intelligent, over-thinking, wisdom seeking, hippyish, frugal, techie, geeky girls?

INTJ forums. We're over-thinky techie geeky nerds who need our alone time. MetaFilter also seems to have more than its share of geeky introverts. Are you in school? Any nerdy groups you can get into? Lecture series? book club?

Then again, you don't need to date someone exactly like you, just someone who complements you. I recommend dating a fellow introvert, but it does take a while longer to find us.

When the hell did everyone go and become sex masters? Seriously. What can I do about this? Do I have to pay a prostitute to work up experience? Arghhhhh.

Hey, you like research and you're on the internet! Bonus!

alt.sex User's Manual
Everything at AskMe tagged with sex

Disclaimer: This course has optional reading assignments, but the hand-on experiments are essential.
posted by heatherann at 10:27 AM on November 10, 2008

To put it another way, partners 1-7, mostly were 1 event people, and the sex was generally not all that great. 8-10 was getting there but oftentimes not stellar. 11-13 have been totally mind blowing.
posted by sully75 at 10:36 AM on November 10, 2008

I work, and I don't make a lot of money, and I like it that way. But there aren't a lot of people that like to learn or are interested in anything besides "making it" among the working poor because so many of them are constantly in crunch mode, barely making it in tough shitty jobs. All they can think about is vegging out in front of the TV for a few hours before bed.

Where do these worlds collide?

At the anarchist bookstore, generally. Are you at all politically active? Consider volunteering for something like Books to Prisoners or Food Not Bombs where you'll meet other people who are similarly interested in social justice and learning while at the same time having enough free time to help people. They're usually [though not always] tolerant of new folks and while it may not be the perfect way to start going about dating, it's a great way to get out there and be useful. I've also found -- your experiences may vary -- that being a social misfit is not actually any sort of handicap in this type of crowd.
posted by jessamyn at 10:37 AM on November 10, 2008 [1 favorite]

any two mature people can have a relationship, it's not about some abstract notion of compatibility. I'm almost certainly wrong about this, but tell me why? how?

I can tell you why this is wrong and how it's dragging you down -- it's not a particularly romantic notion. This basically says, "Anyone will do, as long as neither party particularly objects to the other." And if you express this to her, either outright or merely unconsciously, I doubt it makes you seem like a very special person to be in a relationship with.

If she has the glimmerings of feelings happening but doesn't know what they are, this is essentially an opportunity (and maybe even a request) for you to step up to the plate and demonstrate why she should pick you out of all people. Those embers are unlikely to blaze unless someone fans them, and you can't count on her to do all the work.

As for the sex, are you just grunting and fumbling through it, pretending like you know what you're doing? It's not a threat to your masculinity to let her take charge, or to break the silence and ask her to help you by taking over or trying different things. Try to lighten up the mood so you don't feel like there's some sort of capital-E experience you're supposed to be plugged into.

And just keep trying, with other girls as necessary. Everyone wants to be good at sex and relationships, but few people get to be that way without making a lot of mistakes and experiencing a lot of heartbreak. Accept that as the price you pay for playing and dive in.
posted by [NOT HERMITOSIS-IST] at 10:43 AM on November 10, 2008 [1 favorite]

But there aren't a lot of people that like to learn or are interested in anything besides "making it" among the working poor because so many of them are constantly in crunch mode, barely making it in tough shitty jobs. All they can think about is vegging out in front of the TV for a few hours before bed.

Whoa! Super judgy! Those are some really unkind sweeping generalizations about a whole lot of potential dates. Maybe working on your attitude here will open up some new prospects.
posted by robinpME at 10:59 AM on November 10, 2008

>it's also 60% you having dated INCREDIBLY selfish women.

He'd be better at sex if he had. No quicker way to improve than on-the-job training from someone who just wants to get off. Try making her teach you.

Respectfully disagreeing with you, Bonaldi, here: I don't necessarily consider "someone who just wants to get off" to be the kind of selfish I was thinking about. Someone who is just wanting to get off, but is willing to teach her partner what to do, isn't really selfish, to my mind -- I'm talking more about the women who just lie back and get ready for their world to be rocked, and when that doesn't happen, toss their partner off as a "loser" because he wasn't magically able to read their minds.

There are women who do just want the sex, but also get that it's a team effort, and that it starts with some basic respect.
posted by EmpressCallipygos at 11:17 AM on November 10, 2008

I think #2 is well covered above - find a kind-hearted person with whom you've feelings beyond lust and persist It's about relaxing and exploring and getting out of the over-thinky mode, and in my experience, even sleeping many times with someone who puts you on edge (judgmentally, not tantalisingly) can still be difficult and weird and unfun.

jessamyn is onto something with #1:

At the anarchist bookstore, generally. Are you at all politically active?

Where do you like to go out? What gets you out of the house? Compatible people, and - even better - people who have the same idea of fun will probably go there too. Meeting people through activism could be a good way to make friends, and more friends means more potential partners or introductions, as well as intimacy of the friendship variety. Not everyone involved in politics is necessarily introverted but it's struck me as a place where plenty of introverts can socialise and even go to parties, making their own kind of fun.

If you don't find the kind of thing you'd like to be involved in, maybe you could organise it? Something frenzied like a writing challenge or a 24-hour zine project might be fun and will definitely bring new people into your life, and it could be a one-off if a regular gig is too much to imagine. If it's geared around your uncompromised interests, the audience/participants will probably share them

I fit a lot of your self-description (not so much pseudo-virgin, not really techie, but otherwise) and tend to be a sociable introvert. Reading and writing and making stuff is good and I find lots of downtime essential, but I'm also happy to go out sometimes when it means spending time having good or fun conversation with people whose company I enjoy. While it's not a magic answer and I am currently single (not really by choice, but not frotting constantly either), I keep meeting interesting people through friends and I feel better about myself for all the interaction, and both of those increase the odds of the right kind of relationship.
posted by carbide at 12:05 PM on November 10, 2008 [1 favorite]

not really by choice, but not frotting constantly either

fretting. Good grief, that's a champion typo.
posted by carbide at 12:07 PM on November 10, 2008 [1 favorite]

At the anarchist bookstore, generally. Are you at all politically active?

Indianapolis is completely lacking in anarchist infrastructure. No bookstore. No FNB (though their website says otherwise it's because it hasn't been updated in a while). There is critical mass, but it's only sport bikers that do it, no radicals (I try to show up most of the time just in case they do show up, but I'm losing hope quickly).

It's a great opportunity, right? Except that people have tried and failed so many times before to get something started here that it's depressing (2 bookstores have failed in the last decade), and I've flyered the whole north side to no avail (well, I made one contact for the 500 posters I put up + the 200 'fighting for our lives' that I distributed, all by my lonesome).

Frustrating, to say the least. This city might be killing me. No one knows what a "zine" is here. The only friends I have are old high school friends, and none of them are anarchists or politically motivated at all (as previously mentioned). Maybe if I had friends that were more like me I wouldn't even be thinking about girls so much? There aren't many people like me here, let alone girls, which is why I've developed that psycho-defense that I mentioned up top.

Will it be different elsewhere? I really am at the point where I want to move, but where? Bloomington, IN? Or, as I asked before, Springfield, IL? Chicago? Farther? I've felt all this time that it was just me, and I just needed to try a little harder to reach out, to find those people like me, but now I'm beginning to doubt that assumption a little more with each passing day. It's just that moving seems like such a cop-out! Like I wasn't up to the challenge or whatever.

look at me derailing my own thread, weee!...
posted by symbollocks at 12:54 PM on November 10, 2008

Hee! Best typo ever!

You might want to think about how your issues are likely to be seen by the girl in question.

If communication between the two of you is weak, it's easy for misunderstandings to occur. What you see as nervousness and a slowness in getting off may translate in her head as "He seems really uncomfortable in bed. He's clearly not enjoying himself. It's like he has to force himself to even finish. Am I that unattractive? What's wrong with me?" So then she slips into this swamp of self doubt. You pick up on it, then you get paranoid. The whole thing becomes a vicious circle which plays out over and over again until you eventually break up.
posted by the latin mouse at 1:05 PM on November 10, 2008

Compatibility:
I think you've already come to the (correct) conclusion that your thinking on compatibility is definitely the wrong approach. It sounds to me like you've gotten so worked up and stressed about finding (or forcing) the issue of compatibility - that you are mentally sabotaging yourself and the females are picking up on that. (perhaps they sense it as desperation, or immaturity, I dont know,...) but you arent projecting relaxed-confidence, and thats bad. Unfortunately, compatibility is not something you can force, create, or easily find. Yes, you can increase your odds by hanging out with whatever "scene" you are comfortable in, but even then you just need to relax and let it happen. Have you searched around your local area for a scene or crowd that you might feel comfortable with?.. Metafilter meetups?,.. MeetUp.com ?, some kind of underground anarchy crowd? There must be some forum or IRC chatroom or something online that would point you in the right direction. The "abstract notion of compatibility" IS important. When you find a person you are compatible with, the interaction between each other will be so easy and comfortable and intuitive (like finishing each others sentences) that it will blow your mind. The trick is being patient and having faith that IT WILL HAPPEN when its supposed to. Dont be so obsessed by finding "THE ONE". Focus on being the best "you" that you can, immerse yourself in your hobbies and interests, and get out of the house regularly. If you do this, at some point you'll meet a nice non-selfish girl who will ask you probing questions and your passion for your interests will show through and she'll see that as confidence, etc. Thats the kind of vibe your looking to build. It doesnt happen overnight. Additionally, dont let yourself get in a rut. Your growth as an individual requires new experiences and challenges (big or small) that you can overcome. Yep, you'll fail at some of them. Learn what you can from the failures and try to do better next opportunity. ( i realize alot of this is cliche advice, but I'm sharing it because I believe its useful. )

Sex:
The sex question is a lot easier to answer. I agree with a lot of what others are saying that it sounds like you are interacting with females who are either shallow, selfish or for some other reason not respecting you as a person. Course, if all you are having is 1 night stands, then that reaction is not totally unusual. Sounds to me like you've also come to the conclusion that this isn't working for you. So stop doing it. Yeah, I know, sex is awesome and we'd all like to have mind blowing orgasms 3 to 5 times a week. The reality is "good sex is worth the wait". My advice would be to focus on building a healthy relationship before jumping into the sack with someone. Make sure in your own heart and mind that the person you are close to really truly cares about you and will treat you with respect when you get in bed. Quality is better than quantity.
posted by jmnugent at 1:11 PM on November 10, 2008

Are you active, or more sluggish in general life--you know, desk/computer job, go home and watch tv/play video games/surf the 'net? Because in my experience, the hands down best thing about maintaining some actively physical hobbies is that sex automatically is better. You will have the endurance, strength, and coordination naturally; the rhythm will be instinctively spot-on once you're more in tune with your body in other parts of your life.

And dude, your experiences sound like mine right up until I was in my late 20s! I know I don't have a clue what The Kids Are Up To These Days, but try to remember that yes, you are very young. Take a deep breath; it gets better.
posted by ifjuly at 1:38 PM on November 10, 2008

Anarcho/hippy types?

Easy.
Start looking for Full moon drumming, fire dancing circles etc...

Google shows me here & also mentioned here.

And yep - consider moving.
Find a town where people are a bit closer to your vibe, and you'll find it far more comfortable to stretch to meet them.

I haven't been through much of the states, but wouldn't much of the entire pacific north-west fit your general vibe??
(Except for the pseudo-virgin. Once you find your tribe, it's far easier to be comfortable, and get laid).

Also - sex. I think everyone is assuming this is obvious advice you've seen before, but once you have gotten comfortable, friendly, and really in the mood (you're both nice and warm, maybe a little altered - a glass of alcohol, chocolate, pleasant surroundings and warm but dim lighting [ok, that's just what does it for me]), then maybe just kiss & make out, rather than sex. If you do, ask her what she likes, kiss your way down body, and try oral first (be clean from a shower before date/hanging out).
Ummm. IANA-sexpert? :P
posted by Elysum at 3:08 PM on November 10, 2008

As for sex:

#1) Relax. It's just sex. It's not brain surgery. Even if you do it "wrong," so what? Just use it as an excuse to try again. If you're not relaxed, consider waiting... or consider the possibility that if your partner makes you tense, you might be better off with a different partner.

#2) Tell a girl up front that you don't have much experience and you want her to tell you EXACTLY what she wants. Make it a game if you like, a sort of Simon Says. Good sex requires good communication, and if you're not ready for non-verbal signals, just have her tell you flat out whether she wants it harder, deeper, shallower, faster, slower, whatever. It also can be pretty hott to have someone telling you exactly what she likes.
posted by grapefruitmoon at 3:13 PM on November 10, 2008

Will it be different elsewhere?

Yes, it will. Fortunately, the rest of the world is different from Indiana. Seriously, I think you need to go somewhere where the ground is fertile.
posted by bricoleur at 4:51 PM on November 10, 2008

I think it probably took me having sex 100 or maybe 1000 times before I got close to halfway decent at it. Honestly, I should go back and write apology letters to the first few women I slept with; my vigorous but inept fumblings were no doubt quite the letdown for them.

In other words, the solution is to find someone who reacts to your ineptness by giggling, rather than yelling, and the two of you practice practice practice. Some people are really good at the casual sex thing, and some people aren't. I'm not; if you are like me and need time to loosen up with someone new, don't think you are defective. But if so, also realize that the drunken-bar-hookup won't really make you happy, and you need to find a different route. Taking it slow can sometimes make the sex a lot better, because you first get comfortable with the other person, then can figure the sex out separately, rather than trying both at once.

About the compatibility thing: you sound a lot like me when I was younger (but a lot more self aware). I think I was conflating things that shouldn't really be conflated. I mean, I wanted the anarchist punk rock chick or whatever, without realizing that sometimes the most radical, far-out, self-aware women are dressed really conservative and going to school/working straight jobs/etc.

In other words, I was assuming that you had to look radical to be radical, when really a lot of the time it's the other way around, and you get conformists with blue hair, and amazingly cool people working at the library or sitting at the study carol in grad school. In retrospect, I missed out on some really good opportunities by having my head up my ass.

All of that to say -- maybe you are looking for the wrong signals, and in the wrong places. Those over-intelligent, over-thinking, wisdom seeking, hippyish, frugal, techie, geeky girls (I'm leaving off the "pseudo-virgin" part) are going to be found in all the same places that the people here on MeFi can be found -- in other words, pretty much anywhere.

But if you are going through life thinking "man, all these straights are so dull and boring, they don't get me, they aren't radical at all" -- how are you going to know that the cutie sitting at the cafe loves to read Bakunin? Would you have any idea that the woman next to you just got back from a summer working with a radical women's collective in Turkey? And you aren't going up and having conversations with an open mind -- where you are really listening and hearing where people are coming from -- you'll never make those connections because you are missing out by focusing on the wrong kind of surface signals. It's that old cliche about judging books by their covers -- the kind of girl you are saying you are looking for isn't going to go around with a flashing neon sign on her forehead asking for you by name, you know?
posted by Forktine at 5:06 PM on November 10, 2008 [1 favorite]

With your interests, being online is a good first step---and as a person who considers herself a nice market, I really endorse them as I've found some really compatible people to date there. You need to stop compromising your interests on there! It sucks to wait and feel like everyone else has an easier time of it . . . but if you want someone you mesh with, you need to hold out and keep looking. I have found the quiver feature on there really useful---both for seeing people I should contact, and for seeing how often I accept vs. reject people! It made me feel less like "oh man, I stink, it takes so long to meet someone I like" and more like "well, I like what I like . . . which is not in great supply, I guess."

As for the sex---how far into these relationships are you having it? If you're having it with women you don't really mesh with and having it soon, it's pretty much bound to be rotten. Holding out is a lot easier said than done when you are horny, believe me I know. Next time you have the opportunity and you like the girl and all of that is in place---spend a lot of time doing non-peen related things to get her off, let her get on top, or both. You'll feel better about yourself sexually to see her getting lots o' pleasure, and letting her on top takes the pressure off you.
posted by lacedback at 6:37 PM on November 10, 2008

Therapy will help. You are unecessarily raising the stakes too much.
posted by Ironmouth at 9:46 PM on November 10, 2008

I think you would like Wisconsin or Minnesota better. College towns have the best people in my experience and even in the middle of the Midwest in Illinois you have some places with awesome people like Champaign. I've worked on farms as a volunteer in all those states and met lots of hot anarchists (from anarcho-capitalists to anarcho-primitivists and everyone in between although the farm set tends to lean to the latter) and nothing attracts the frugal/hippy/intellectual set like organic farms. Working on a farm also gives you a nice body, I must say. Try localharvest.com (there are some programs where you work and get food as part of a CSA) or wwoof.org/. You could also try looking for an intentional community, since there are a few that are anarchists. In all these situations you'll meet tons of awesome people, get food (and sometimes free board), and get in shape. Even IT nerds can fit in...I met tons of programmers while working on farms, so I wasn't the only computer nerd and most farms were actually quite thankful I was a nerd because I fixed their websites.

Yeah, I always recommend working on a farm for things on MF, but I see from your librarything that you have read some books that are popular with myself and other farm volunteers I know.
posted by melissam at 6:36 AM on November 11, 2008 [1 favorite]