How do I overcome my lack of relationship experience?
July 23, 2012 3:15 AM   Subscribe

I'm a normal, well-adjusted, heterosexual, 30 year old male. And I'm a virgin. How do I get past this?

Forgive me, as this is very long. I sincerely would appreciate advice, though. This has taken me a couple of days to write, and has involved some fairly serious self-reflection.

I am a 30 year old heterosexual male. I am normal and well-adjusted. I am intelligent, funny, well-read, interesting, well-spoken, multi-lingual, talented, competent, and well-educated. (And, quite obviously, humble.) I am pretty average in appearance, but not, I think, unattractive.

Furthermore, I work in the service industry, and I interact normally with strangers of both sexes daily. I have many male and female friends and acquaintances, including close friends of both sexes. In my job, I interact with a large number of very attractive women, with whom I get along very well.

But I have never had a relationship. I have never been intimate with a woman. I've never been on a date, never had a kiss, never had a girlfriend, and never felt love.

(A couple of quick caveats. First, I am not entirely unhappy alone. I am happy with myself and enjoy my own company. I have a variety of interests which keep me engaged and entertained. I am somewhat naturally introverted, so spending time by myself doesn't bother me. And, I've been alone so long that I'm comfortable with it. It does, however, make me feel like I'm missing out on a vitally important part of life, and it's getting to the point that it's bothering me. I feel like I am missing out on life by not experiencing an emotion that is so widely discussed, written about, desired, and craved. Second, I would like to stress that I'm not as concerned with my virginity as I am with my overall lack of experience. If I was primarily concerned with my virginity, I'd hire a hooker and be done with it. I'm more concerned that my social development is deficient in some way, and that in the long term, it's going to be a detriment to my happiness.)

There are a couple of factors that play into this, I feel.

The first of these issues is self-perpetuating: The fact that I'm inexperienced makes it increasingly difficult to get experience.

I lack the experiences that everybody else started building when they were adolescents. That part of my social development simply never happened. My parents didn't allow me to date in middle school. I didn't date in high school. (Overall, I feel that this was probably a good idea, as I doubt that I was emotionally mature enough to handle adult feelings then.) I didn't date during college, either, for a variety of reasons, none of them very good. (I lived at home for a large part of my undergraduate experience, I was hung up on a girl who had a boyfriend, etc.) After college, I found my inexperience actually hampering my chances. Awkwardness and inexperience is expected among 14 year olds. After 25, though, it's weird. It's expected that you've had a few experiences by 25, and if you haven't, it's twice-weird. First, because you're expected to not be an awkward freak, and second, because of the underlying implication that somebody who is inexperienced at such an age is inexperienced for a reason; that is, something must be wrong with him. If he was normal, someone would have banged him by now.

The inexperience manifests itself as a problem in a couple of ways. On the purely mechanical front, I don't know how to kiss. Never done it. Nor do I know how to have sex. I mean, I understand it in theory, but that's about as far as it goes.

More importantly, though, is the social front. I don't know how to make a girlfriend. I make friends easily and well. But I've never gone from meeting a girl who I find interesting to being in a relationship with her. I simply don't know how it's done. In fact, I think part of my problem is that I meet a girl who I find interesting, and I make a friend out of her, because it's what I know how to do. I am "friend-zoned" often, and it's probably in large part my own doing.

I don't know how to indicate my interest to a girl. My general M.O. is to hang out with a girl until she gets the idea that I must be interested. So far, that hasn't worked out for me--we usually wind up being friends. Similarly, I don't know how to tell when a girl is indicating interest to me. I was hanging out with a group of friends a while back, and after everybody left, one of my friends asked me why I hadn't spent more time with a particular girl in the group. I asked him what he meant, and he told me that the girl had been flirting with me the whole night. I had a very slight feeling she might be interested, but I never picked up on the flirting. This is even more confusing when combined with my propensity to end up in the friend-zone, since I can never tell if I'm already there, or if I'm still in the ballgame.

Furthermore, I have no idea what to do when I'm alone with a girl. None. There have been a few instances in my life where, I am certain, if I had known what to do, I would have ended up having sex. I was with a girl to whom I was attracted, and who was attracted to me. But I didn't know what to do. Once I am in a situation where it's just me and the girl, I don't know what to do. I don't know where I should sit; if I'm sitting next to her, should I touch her?; if I touch her, how should i touch her?; how does the conversation change from "wow, that's some crazy weather we're having" to "how's about we fuck"? I don't know how to learn these things. It doesn't seem like there's a class you can go to that will let you role-play these situations.

The other factor, and almost certainly the most important one, is that I have some self-confidence issues.

Most of these are related to body image problems. In high school, I had pretty severe acne. (This was mostly cleared up by a couple of courses of Accutane, so it's no longer a concern.) After high school, I gained about a hundred pounds. I've recently lost about 70 of that, so I'm looking better now, but the self confidence issues remain.

If I try to look at myself from an outside perspective, I know that I'm an intelligent, interesting, and funny guy. But inside, I feel like I'm not deserving of an attractive girl. I constantly tell myself that an attractive woman wouldn't be interested in me--she's just talking to me to be friendly; or, she just keeps touching my hand by accident; or, she's not going out of her way to hang out with me, it's just that we happen to be out at the same time and she's got nothing better to do, so she has a drink with me.

This, I feel, is an important part of why it's easier for me to interact with girls on a "friends" level than on a "potential partner" level. After all, if we're just friends, she doesn't have to be attracted to me, so it doesn't matter if she thinks I'm a schlub.

My self-confidence issue manifests itself in a couple of ways. First, it makes it difficult to interact with a girl to whom I'm attracted. I'm always thinking that she's not into me as much as I'm into her. It's hard for me to tell if a girl is hanging out with me because she enjoys my company, or because she's not willing to tell me to go away. (I realize that it's more likely that she enjoys my company, but, empirically, the outcome has always been that I don't end up with the girl, so the other option is a very real possibility.)

Second, it makes it difficult when a girl explicitly shows interest in me. When a girl hits on me, my anxiety soars. I get nervous, I clam up, and I withdraw. In fact, the more direct a woman is in expressing her interest, the more anxious and nervous I get about it. My job requires me to dress up, and be around attractive, drunk women on a regular basis. A couple of nights ago, one woman--in so many words--offered to take me back to her place and show me a good time, after I got off work. She was a little older than I'd normally be interested in, but she was hot, and friendly, and interested. But I get nervous and withdrew, and turned her down. In retrospect, I'm not sure why. I'm afflicted with a strange emotion that I can't really define. It's a weird mix of embarrassment, anxiety, and shyness.

Third, if it comes to a situation wherein I'm competing with another guy for a girl's attention, I lose. More accurately, I concede. This has actually happened a couple of times in the last several weeks. I've been hanging out with a girl, and another guy starts showing some interest. The little voice in my head tells me that she's clearly going to be more interested in him, so I pull back, and tip my king. I don't know how to tell the other guy to fuck off, and, more importantly, I don't know how to convince myself that I should tell the other guy to fuck off.

Other complicating factors:

I have fairly strict standards. I require a woman who is intelligent, interesting, and at least somewhat attractive. My standards are probably too high, but I am unwilling to compromise on them. I'm just not attracted to dumb, dull, or ugly.

I'm not completely opposed to casual sex, but it can't be completely casual. In order for me to be seriously attracted to somebody, there has to be at least some emotional connection. That is, I'm generally more attracted to a girl that is a friend than I was to the same girl before she was my friend. If Mila Jovovich came up to me off the street and offered to take me to bed, I don't know how I'd respond. Generally, I have to know somebody, and have some level of emotional attraction to her, before I'm sexually attracted to her.

Finally, I am pretty risk-averse. I am the kind of person, who, when faced with a challenge, prefers to research everything about it, work out every possible outcome, research each of those possible outcomes, and then make my decision about a course of action. If the girl I was hanging out with were to say "okay, now it's time for you to kiss me," then I'd probably be okay, but that kind of situation doesn't seem to present itself very often, and the uncertainty makes it that much more difficult for me.

So now, my question. What advice do you have for me? How do I fix this? I can't really ask my friends about this, because, with the exception of one close female friend, nobody even knows about my situation. (I mean, I'm sure some of them have probably put it together based on the fact that for the whole time they've known me, I've never been in a relationship, but it's never been explicitly discussed.) So I turn to you, anonymous strangers whom I will never meet--how do I get past this?

TL;DR: I'm a normal guy, but I've never had a relationship. I'm inexperienced, and have some self-confidence issues. How do I get past this?
posted by ann on a mouse to Human Relations (58 answers total) 40 users marked this as a favorite
 
This is a well thought out question. It's got multiple parts, so I'll take the easiest one.

My general M.O. is to hang out with a girl until she gets the idea that I must be interested. So far, that hasn't worked out for me

There's a much easier and more effective way. Go to the woman of interest and say, "I'd like to ask you out on a date. Would you like to go with me to [activity] on [date]? I can pick you up at [time]."

You don't have to wait for some secret sign that she's interested, or for her to pick up on your subtle clues. Just ask. Sometimes a woman will say no, and that's ok. Sometimes a woman will say yes and that's better than your current results.
posted by Houstonian at 3:32 AM on July 23, 2012 [19 favorites]


Finally, I am pretty risk-averse

I'd work on overcoming this in low-stakes ways that are outside of the relationship / sex question. In other words become more comfortable with taking a risk. Not every outcome can be known and some things can be missed or ruined by too much research or being hesitant. Re-learn some fearlessness. Then bring that perspective to bear on your relationship concerns.
posted by safetyfork at 3:42 AM on July 23, 2012 [3 favorites]


Following what Houstonian said, if you're uncomfortable/anxious with the idea of asking a woman you are interested in out on a DATE (in so many words), why not invite her along to something you both might enjoy, even if it involves a larger group of people, and if that "works," then escalate to a more "date-like" encounter.
posted by kuanes at 3:51 AM on July 23, 2012


You say you're not specifically hung up on the virginity thing, but many of your examples of disappointing interactions with women seem to fast-forward past the bulk of the encounter to focus on your inability to close on sex at the end ("how does the conversation change from "wow, that's some crazy weather we're having" to "how's about we fuck"?).

If you're at some level entering every single encounter with a woman expecting that it might (in one fell swoop) be your first date and first kiss and first love and first intimacy and first sex.. well, that's a lot of pressure on yourself, and on her. I can totally see chickening out of that at the last minute, or standing aside and waving some other guy in. You're doing that rope-climbing thing where you look all the way up at the top of the rope, when you're really just supposed to focus on the next foot you have to climb.

For that reason, I really like safetyfork's idea of focusing on incremental low-stakes goals at first, even in the realm of relationships. If you think about the "average" way guys learn this stuff in high-school/college/postcollege, nobody gracefully selects a woman who's the perfect combination of physical attractiveness, intelligence and personality, then woos her in a whirlwind week of perfectly executed dates and beds her that Saturday night. Seems like people just pick someone nearby that they kind of like, then focus on getting into some sort of interaction, THEN focus on getting to hand-holding, and only THEN think about maybe a kiss, etc. What if you put sex (or even making out) off the table altogether for now, and just set yourself the immediate goal of getting a woman one-on-one in some sort of romantic context? Then, when that goes well, maybe try to repeat it with someone else you like, and so forth, and then after a month or so you won't be the guy who's never been on a date or kissed or had sex, you'll be the guy who's been on several dates but has never kissed anyone or had sex. At which point, raise the bar, rinse, repeat.
posted by Bardolph at 4:11 AM on July 23, 2012 [29 favorites]


I second explicitly bringing up the date option to the target of interest. But yeah, it's tough to phrase it like that, especially since you're risk-averse - I'm the same way when it comes to women. That's why I tend to prefer dating with strangers, where it doesn't matter as much if the date turns out to be a disaster or you are rejected.

Also, have you tried dating websites? Everyone's there for the same reason, so no one's going to beat around the bush - If they are into you you will know right away, and vice versa. It would allow you to start up a friendship through the net (since you said you would prefer dating friends to complete strangers), and you both can proceed at your own leisure before you feel comfortable enough to meet. You can also bring up the fact that you're not experienced if you want, so you can specifically target women who would be okay with that.
posted by Kamelot123 at 4:12 AM on July 23, 2012


Dating is high-stakes. Nobody likes rejection, but you need to get to a stage where the potential for rejection is not a referendum on your self-worth. I would suggest Rejection Therapy.

Second of all, were I you I would seriously look at online dating simply because it removes the ambiguity - it isn't called Online Friends. Sure some people become friends after a date, but the default setting is Not Friend Zone. It would also give you some more experience, both with rejection (online dating is a numbers game) and with actual dates - having coffee wit someone is actually pretty low stakes.

I wouldn't worry about being freaked out by really aggressive, and particularly aggressive and drunk, women. When what you're looking for is fundamental driving lessons and what someone is offering is "drive around the track in my Ferrari, baby!" it is perfectly logical to panic. I would - that's way too much way too fast. You need to acquire skills and confidence incrementally.
posted by DarlingBri at 4:19 AM on July 23, 2012 [4 favorites]


I'm not completely opposed to casual sex, but it can't be completely casual. In order for me to be seriously attracted to somebody, there has to be at least some emotional connection. That is, I'm generally more attracted to a girl that is a friend than I was to the same girl before she was my friend. If Mila Jovovich came up to me off the street and offered to take me to bed, I don't know how I'd respond. Generally, I have to know somebody, and have some level of emotional attraction to her, before I'm sexually attracted to her.

ann on a mouse, I don't think you're being honest with yourself. I get where you are coming from, but really man, you're taking this all too seriously and doing yourself a disservice.

I think you need to get laid without any emotional strings. Get that "virgin" thing out of the way and I think you'll be in a better stance to start the sort of relationship you want.
posted by three blind mice at 4:21 AM on July 23, 2012 [3 favorites]


I have fairly strict standards. I require a woman who is intelligent, interesting, and at least somewhat attractive. My standards are probably too high, but I am unwilling to compromise on them. I'm just not attracted to dumb, dull, or ugly.

Nor should you be. However, guys who say this are pretty consistently ... not great. You've never actually dated anyone, so you don't have any idea what those standards mean, and its very hard to tell if someone is right for you until you've had some experience with the wrong people. Dating is, in many ways, a series of negotiations, and you sound like you might be acting in bad faith.
posted by modernserf at 4:32 AM on July 23, 2012 [49 favorites]


I'm not quite sure what kind of experience you are looking for but I find it concerning that you would ask 'How do I get past this?', is that what you want, to get past it? The whole relationship thing is meant to be enjoyable, it doesn't sound like you expect to enjoy it too much if you want to just get it done so you can tick a box. You don't have to conform to an arbitrary social norm however pervasive it may be if you don't actually want to.

Here's something a little more practical: try looking and smiling at one of your female friends for a little longer than usual and see if she smiles back, baby steps and all that.
posted by freshfish at 5:04 AM on July 23, 2012 [1 favorite]


I don't know how to indicate my interest to a girl. My general M.O. is to hang out with a girl until she gets the idea that I must be interested. So far, that hasn't worked out for me--we usually wind up being friends.

I know you flippantly suggested saying 'how about we fuck'... but my first boyfriend was a guy who I met at a party, and as soon as we were alone he sort of blushed and said "Uh, I really want to kiss you now." We dated for three years!

You describe many instances in which you could have had a date/sex/a kiss, if you had just asked for it. Yes, even if you didn't 100% know what the outcome would be. If you start asking girls out when you think there may be interest, you will almost certainly be rebuffed a few times. But your success rate now is a big whopping zero percent, so screw it. Just start asking. That is all you need to do. Journey of a thousand miles starts with a single step, etc.
posted by showbiz_liz at 5:18 AM on July 23, 2012 [4 favorites]


I am thinking of what I'd tell my friend N, who I'd guess is around 30 and not sexually or romantically experienced. I can tell he's interested in me, but I have NO interest in or attraction to him. It isn't his physical looks, it's that he has no idea how to stimulate another person emotionally or physically (especially emotionally) because he completely lacks experience. Me, being an attractive, nice, intelligent, etc person... I have options and really will probably never be attracted to him, unless I suddenly have no options. What I would advise N is this:

Trying to get closer to your single female friends is really unlikely to bear fruit. What you probably don't understand is that even for people who are experienced and skilled at the arts of seduction (whatever that means), it's STILL the case that generally 99/100 people you fancy do not like you back. It's not personal. It's true for most people... it's not like in the movies where oftentimes you like your friend and they like you back. (Maybe in college, unlikely with inexperienced 30 year olds.) Don't waste your time thinking about or aiming for the impossible.

To get a hit, or multiple hits, you really need to go where the chances are better, and have the bravery to show your imperfect self to lots of people. Don't try to fit your round peg into square holes. (Ahem.) Which means: online dating. Women of all shapes and sizes. Push your attractiveness boundaries. Consider poly women. Lots of activities. Work the numbers. Tentatively and ineffectively approaching one woman for months (like N did with me) is just such a giant waste of time. You need to not fear rejection and have the goal of getting some experience, if you so choose. It's what I would tell N to do. Do it ethically and honestly, but aim to build up your confidence. Realize that there will be lots of rejection and it's not the woman you choose who will want you and sleep with you - it's that 1 woman in 100 who is drawn to you for a random and inexplicable reason.

Also know this. Dating isn't like that for you because you're broken or inexperienced. It's like that for everyone. I am attractive, and the guy I've had my eyes on and liked has not liked me back (ever). Dating, for me, means bracing myself for rejection and getting out there to find a match for a random and inexplicable reason. In the process, building up my skills and attractiveness so that maybe connections will be more frequent rather than less (or more lasting rather than less).

If I were you, or N, I'd set a short term goal of just getting some experience, which means having an attitude/intention somewhat like I described above. Don't fear the short term, the numbers game, and the imperfection. Finding real lasting romance and love can come after that.
posted by kellybird at 5:21 AM on July 23, 2012 [8 favorites]


Would you consider retaining a sex coach (subset of sex therapy) to help you gain a little experience with constructive feedback? They are skilled at working with novices in a caring and nonjudgmental way, both on "the mechanics" of how to kiss, touch, etc. as well as the interpersonal dynamics of flirting, reading nonverbal signals, etc.
posted by carmicha at 5:30 AM on July 23, 2012


And another idea... to become accustomed to relaxing when touched (another plus of working with a sex coach, by the way), what about getting regular massages? I'm thinking that it might help to become more attuned to your body, especially given your recent impressive weight loss.
posted by carmicha at 5:35 AM on July 23, 2012


Online dating is made for your situation. You will have your first date. Eventually you'll have your first kiss. Some time after that, you may have your first girlfriend and your first sex.
posted by J. Wilson at 5:44 AM on July 23, 2012 [6 favorites]


Seconding carmicha: You really need somebody to show you the ropes - but there are two distinct sets of ropes. The first is about having sex for the first time - and hence removing that elephant from the living room. The second is how to have further, longer term, relationships with women - which is actually more important. You could look around (on-line would be a good place) for a woman who was willing to to work with you on the first problem - and then consider seeing how things turn out after that for a possible deeper relationship. But how things would end up would be a big unknown for her (and you) - I think many potential partners would be put off by that proposition. My guess is that, while you may feel you are an extreme outlier - sex coaches deal with people like you regularly. So sort out the sex, the body language and the anxiety first - then get dating.

On the specifics of how to behave on dates I would recommend having a look at "Would like to meet" - old BBC series. Look at what the "expert panel" advise for their various subjects and see if any of that could apply to you.
posted by rongorongo at 5:46 AM on July 23, 2012


I have fairly strict standards. I require a woman who is intelligent, interesting, and at least somewhat attractive. My standards are probably too high, but I am unwilling to compromise on them. I'm just not attracted to dumb, dull, or ugly.

This makes me wonder if you give people a chance--a chance to get over their nerves or awkwardness and share what's authentically interesting about themselves, and a chance to become attractive to you.

You may be setting your sights too high, expecting perfection when you don't have perfection to offer. Imagine a woman saying she has strict standards and would never go out with a man with no experience, or who is still 30 pounds overweight.
posted by parrot_person at 5:50 AM on July 23, 2012 [15 favorites]


There's no perfect script any of us can give you. Everyone has their own M.O. and pretty much the only similarity across the board is that you have to actually try to express interest in order for the person to pick up on it. Sure sometimes you'll screw up, but that happens with everyone. It honestly sounds like you're so concerned about being rejected or looking silly that you've opted to do nothing instead; but guess what, that leads to the same outcome: no dates.

Stop treating every woman you meet like a potential first everything. Stop hanging out with women as friends hoping that they'll magically get that you're into them. If you don't know all the body language cues, you're going to have to go for awkwardly sweet direct statements/questions. Yeah it's going to be anxiety inducing but that's part of the fun: the surge of anticipation, anxiety, the butterflies, the near freak out you have when you finally get the guts to ask someone out.

Honestly, I'd focus on the relationship side before the sex stuff. If you have an understanding partner and you're willing to listen to what she tells you, sex will be easy enough to manage (though awkward at first). Try online dating to go on a few low stakes dates. Ask out the girl you like (you'll probably be awkwardly blunt here and that's OK). Stop coming up with reasons not to do it and dive in.
posted by buteo at 5:51 AM on July 23, 2012 [1 favorite]


One other small point that may have other ramifications... in your post, you refer to all of your prospects as "girls." Yes, that's a little icky: they are women. However, it dawned on me that in this aspect of your life you are, from a development perspective, still a teenager. That may mean you should also expect, and be ready for, some of the other things that bedevil teenagers, including inappropriate crushes, confusing sex with love, etc., all of which can do a number on you. For this reason alone it would be helpful to have a sounding board as you navigate these new waters.
posted by carmicha at 6:09 AM on July 23, 2012 [2 favorites]


When a girl hits on me, my anxiety soars. I get nervous, I clam up, and I withdraw. In fact, the more direct a woman is in expressing her interest, the more anxious and nervous I get about it. My job requires me to dress up, and be around attractive, drunk women on a regular basis. A couple of nights ago, one woman--in so many words--offered to take me back to her place and show me a good time, after I got off work. She was a little older than I'd normally be interested in, but she was hot, and friendly, and interested. But I get nervous and withdrew, and turned her down.

So here's what you do. Since this probably happens to you every once in awhile, take the next woman up on this. You're very hung up on being inexperienced, but inexperience doesn't always equal bad. I think you think it's way more complicated than it is, especially kissing. Kissing takes about 15 minutes to get right, especially if you're aware of what your partner likes.

Sex takes longer, but it's about listening and paying attention to what she likes and what you like, and what's good for one partner isn't always what's good for another, but the basics are the basics.

Overall, being scared of kissing and sex is going to be the biggest turn-off. Once you get the idea out of your head that you need a Master's-level course in the art of seduction to be worthy of a sexual partner, you'll be much closer to having a dating life.
posted by xingcat at 6:09 AM on July 23, 2012 [3 favorites]


I would address your lack of confidence by finding some area in which you can genuinely challenge yourself and succeed. For example, for a period of time I was rock climbing with a group of friends, despite being unathletic and afraid of heights. Directly confronting this phobia (and the more nebulous sense of "I can't do sports") for 10-20 hours a week had a huge effect on my confidence in other, completely unrelated areas of my life. When I met my future wife during this period, I found that I didn't need to think about how to be act confident -- I simply was confident, and everything just progressed spontaneously and easily.

Worrying about some idea of a "friendzone" is only going to make you more self-conscious, as is worrying about your virginity. More strategizing and rumination about your behavior is only going to make the problem of self-consciousness worse. Getting more comfortable with yourself, and with taking risks in general, is going to help get you get out of your head here.
posted by inkfish at 6:18 AM on July 23, 2012 [2 favorites]


The question you should ask yourself is how do *you* want to "get past this"?

Now forgive me for possibly overanalysing your choice of words, but since written language is all that's on display here, I find the way you choose to express yourself on this very interesting and perhaps a clue in itself - for instance:
I feel like I am missing out on life by not experiencing an emotion that is so widely discussed, written about, desired, and craved. Second, I would like to stress that I'm not as concerned with my virginity as I am with my overall lack of experience. If I was primarily concerned with my virginity, I'd hire a hooker and be done with it. I'm more concerned that my social development is deficient in some way, and that in the long term, it's going to be a detriment to my happiness.
What I notice very clearly here is your use of the passive and impersonal - "an emotion that is so widely discussed, written about, desired, and craved"... by? "widely", ie. by other people, not by you? You are posting this, but you don't sound a bit like you actually desire and crave a sexual relationship with a woman, the sex in itself or the emotional connection and all that. You say you are "concerned" about your development being "deficient". This is language that sounds very unemotional for such an intimate issue. It goes through your whole post, this sort of emotional distance and remove. This and your list of qualities and the fact you clarify you're happy enough alone and the list of caveats and "high standards"... it all gives an impression of something you're sort of pondering and considering from a theoretical perspective only, or from the point of view of thinking only about the absence of this experience as a piece of an otherwise perfect puzzle.

What I get the feeling is missing from your text is something very basic, the one requirement to get kissed and/or laid the first time ever, at any age, for everybody... a real desire and a real interest in women in general (since you're a straight guy, of course, else it'd be men!), and in some women specifically... like, oh wow that girl I saw at the party/in class/at work etc. makes me drool/go weak at the knees, rawwrrrr, etc. (sorry for silly language, first thing that comes to mind) - all the physical and emotional reactions you get from fancying someone. The attraction itself!

Do you feel that? How do you feel it? what kind of fantasies pop into your head when you feel attraction to someone? Because that's where everybody starts from, at 12 or 18 or 25 or whatever age...

It sounds like you're treating this in a "clinical" way, in a way that removes all your own personal feelings and desires from the equation. Maybe it's just your choice of words in posting on a public forum. Again apologies for possibly overanlysing language (and repeating myself - writing this quickly off the top of my head). But you have written a lot and it sounds like you thought about it a lot, so if that reflects your approach to this "issue" that you want to "get past", well, I'd ponder a bit more on that approach first and foremost. Open up a bit with yourself first, and ask yourself those questions about what you want, what you feel, what you crave for yourself - nevermind what others crave or notions of what "social development" should be.

- Anecdote which may or may not be interesting or useful: I've known someone, a friend of a friend, who was a virgin up to his early 30s. He'd never had a girlfriend, relationship, kiss, nada. I remember he was an extremely polite guy, formal but friendly, sort of "old style gentleman" almost, easy going enough with his mates and well liked by them, successful in school and then work, he just had this sort of hang up about women or something, I don't know. He wasn't really shy or insecure. He was perhaps a bit too precise and fastidious I guess, at least based on other things about him, the way he dressed, that kind of thing - not in an unpleasant way, but you could see this was not the sort of guy who'd gone through the classic teenage experiences of getting awfully drunk, or stoned, or smashed at least a couple of times; it wasn't the kind of guy who'd have a crush on a celebrity or singer or actress; or gone through being a heavy metal fan or discovering punk and getting matching hairdo and clothes etc. (all stuff I'd seen his close mates go through at some point). You'd get the impression he wasn't the type to just "let go". Then, when he moved out and away from where he'd been born and grew up in, he got a better job and met a lot more people and maybe had the chance to become a bit of a different person or at least unlock something that was a bit too contained before. I am only guessing. But basically he had a series of long term relationship including living together with the girlfriend of the time. Anyhow, last I saw him - with the girlfriend - the change was noticeable even in his appearance and it wasn't just the years - he'd put on a bit of weight, looked a lot more relaxed, had the same politeness and formality about him, but in a way that looked a lot more comfortable and at ease, like, mellower. And in a way that gave the impression he really is interested in other people. And in women. And in his girlfriend in particular. I don't know (or care! tmi!) at which precise moment and how he "got past" being a virgin and having no relationships at all for so long, but well, I'm happy he did, he looked happier and his girlfriend looked happy and comfortable with him. He somehow got out of his own "box" and made himself and someone else happier. Whichever path he took to get there, I think that is the primary impulse - openness, risk taking, genuine interest.
posted by bitteschoen at 6:22 AM on July 23, 2012 [4 favorites]


You've bundled up so many issues into one big lump of anxiety that it is hard to know where to begin.

Number one is that if you are feeling anxious or unhappy about something, that's all the reason you need to chat with a therapist. Unless you get head into a happier place, I don't think the rest will follow.

Number two is I kind of agree with the person above who pointed out that although you say it's not about the virginity, it comes across pretty clearly that it is indeed about the virginity. There's nothing wrong in my book with visiting a competent and professional sex worker (ideally in a legal setting, as in this ask-me-anything on Reddit; that person says she even gives discounts to first-timers) to get the first time out of the way, and then move on to dealing with all the relationship questions separately. Wear a condom, and just say you had a "one night stand" if you ever need to say anything.

As a side-note, though, your use of "hooker" instead of something more neutral like sex worker is kind of like your use of "girls" and your odd emphasis on "high standards" -- taken all together, it isn't exactly a glowing expression of respect for women, you know? If some aspect of this is coming across in person, it might explain some of your problems; a dispassionate outside observer could hopefully see if this is the case and suggest alternative ways of handling things.

Which gets me to number three. There have been several FPPs over the years on sexual surrogacy, the (controversial) use of intimate contact for therapeutic goals. You don't need that, but you would be an outstanding candidate for a dating surrogacy service -- someone who could work you through various scripts and how-tos for everything from flirting to asking out to being on the date. I'm know I've read about these kinds of dating acting coaches before, and if you could find one it would be money very well spent.

But lastly, I'll just say straight up that this stuff is hard. I don't care how many relationships you have had, it is still hard to figure out whether someone likes you, whether or not it is appropriate to ask someone out, and what to do when you get there. I think it's a lot more about being willing to put yourself out there and risk rejection (including setting up situations where things are clear enough -- "Would you like to go on a date with me?" -- that the other person can say yes or no) than it is about having previous experience.
posted by Forktine at 6:32 AM on July 23, 2012 [8 favorites]


You brush it off as not the solution, but I would pay for sex and take virginity off the table. It will give you more confidence.
posted by JohnnyGunn at 7:01 AM on July 23, 2012 [1 favorite]


Advice I've given before:

Have high expectations for who you'll be in a relationship with, but low expectations for who you'll go on a first date with.
posted by no regrets, coyote at 7:48 AM on July 23, 2012 [15 favorites]


I think you're thinking too much on the sexual aspect of dating. By focusing so much on this end goal - and attributing such disproportionate importance to it - you create a lot of performance anxiety for yourself.

Personally, when I date, my focus is not on sex but on trying to get the other person to fall in love with me. I think this is far more important because:

1) Once somebody is in love with you, she will tend to overlook your shortcomings, so your nervousness will become an endearing quality rather than a negative trait.

2) Learning the psychology of attraction is a useful life skill that can help in all sorts of other contexts, even in business. (Developing platonic attraction isn't that different, you know.)

3) The sex is much better.

It's OK when you're dating a woman to pull back and say "Sorry, I'm really attracted to you, but I just don't want to move too quickly." Granted, a woman who is just interested in sex may be turned off by that, but a woman who is falling in love with you will be intrigued and may actually respect you more, in fact.

Hopefully this helps take the pressure off you, at least a little. Also, I don't recommend mentioning how inexperienced you are until after you're hooked up with somebody. When you do bring it up, I recommend just saying it is a mildly joking way, like "I'm not sure if you guessed this, but I'm a little inexperienced at this... so if you could give me a few pointers on how to improve, I'd really appreciate it."
posted by wolfdreams01 at 7:59 AM on July 23, 2012 [3 favorites]


It gets recommended around here all of the time, but if you haven't read it yet, the SIRC Guide to Flirting is a quick read and it lays out the basics of how to flirt (and likewise, how to recognize when someone is flirting with you).

The super-condensed version of the SIRC Guide: if you are at a loss for a topic with a cute girl, say something inane about the weather, because they've proved that works just as well as anything else, and if someone touches you a lot and gets into your personal space alot (that is, less than 18 inches or so) and doesn't move away when you touch them or get into their personal space, then they are attracted to you. Ask them out on a date! Or if you're already on a date, kiss them!

Also: you might feel like there's an ideal version of yourself who can make a move on a woman perfectly smoothly, and that might be holding you back from making a move on anyone, because you can't live up to the idea in your own head. But no one else can see inside your head, and plenty of people will be okay with it if you are not perfectly smooth.
posted by colfax at 8:16 AM on July 23, 2012 [2 favorites]


A few things:
  1. Risk aversion has to go. Start taking risks. Not stupid risks or spectacular attention-grabbing moves, but not merely symbolic risks either. You have to learn to evaluate and push through low-grade habitual fears that are pointlessly holding you back from things you want.
  2. Whenever you find yourself entertaining Othering beliefs about women, reject these beliefs and whoever fed them to you. Repeat to yourself: women are (only) human. You're just dealing with people. This includes any dating advice you read that's based on a gender-vs-gender model of tricks and manipulation. Even if such things get you laid, you'll have years of toxic thinking to wash out of your head after. Stop thinking of women as prizes go get, things a person deserves, etc. They're people you may or may not manage to connect with. That's it.
  3. You're conflating "flirting", "asking out", "having a date", "kissing", "sleeping together", "being someone's boyfriend", "having a relationship", "being in love", etc. These are all different activities, especially in the mind of a 30yo. You're burdening each with all your ill-formed beliefs about the others. This will not serve you well. Treat each event as its own event, that might be all you do with a given person.
  4. Swear off the "I'll just hang around and she'll get the idea" strategy. It doesn't work for anyone, men or women. People generally like direct signals, so long as they're delivered with tact. This means flirting. Flirting is just "direct signals" condensed to a subtle and tactful enough level that they're deniable by each party. There are explanations elsewhere, but it's a simple language that's pretty unambiguous once you can hear and speak it.
  5. Forget your damn "standards". They're part of your bi-modal self-image, it's pure self-absorption. Get over yourself. You swing between speaking highly of yourself and trash-talking yourself. This is a strategy to avoid reality in favour of fantasy: you're either the king of the world or a gutter wretch. Bad news: you're neither. You're a guy who wants more connection than he's had. So go work on connecting more. That's an activity and you've a clearly-stated desire to to do more of it. Activities happen in reality; standards and judgments (about self and others) happen in your head.
  6. When you get around to a part with physical mechanics you don't really know, the phrase you're looking for is "I'm a little new to all this". Everyone's new at some point. Don't overthink it. Just admit it and let her show you what she's into. You'll probably get it wrong a few times anyways (extra reason why your standards don't, at this point, matter much). You can figure out what you're into later.

posted by ead at 9:16 AM on July 23, 2012 [21 favorites]


As others have said, online dating takes the whole "is this a date or not?" thing off the table from the get-go. Start there.
posted by Sidhedevil at 9:20 AM on July 23, 2012


Following what Houstonian said, if you're uncomfortable/anxious with the idea of asking a woman you are interested in out on a DATE (in so many words), why not invite her along to something you both might enjoy, even if it involves a larger group of people, and if that "works," then escalate to a more "date-like" encounter.

This is what I generally do, but it seems almost counter-productive. In that situation, I don't know if she's hanging out with me because she's interested in me, or because she just doesn't have anything better going on and wants to hang out. There's so much ambiguity in "hanging out."

But the flip side, asking somebody on a "date," is almost even worse for me. I get that same, weird feeling--the mix of anxiety, embarrassment, and shyness. It's like a small child being caught somewhere they're not supposed to be. I feel like I have no place in the dating world--it's a completely foreign environment for me.

More responses to follow, later.
posted by ann on a mouse at 9:42 AM on July 23, 2012


I get that same, weird feeling--the mix of anxiety, embarrassment, and shyness.

I shit you not the first time I ever asked anyone out, I got so lightheaded I almost fainted. Tunnel vision. The sweats. I walked into a display cabinet at the department store she was working in. It was rough. And, yet, I rode through it being rather giddy at the fact that a) I actually had the balls to do this and b) she said 'yes.'

Having been, like every other man out there, in situations where I was rejected, I can tell you that you need to do is concentrate on that part of yourself that feels damn proud for having tried, regardless of the outcome.

You can either spend your time thinking about how weird it all is and how hard and how you can't bear to do it, or you can use that time to convince yourself that no matter how poorly it goes, you will not explode, no one will ridicule you, no one will hit you, and the rejection will be mercifully quick and to the point.
posted by griphus at 10:05 AM on July 23, 2012 [3 favorites]


It's like a small child being caught somewhere they're not supposed to be. I feel like I have no place in the dating world--it's a completely foreign environment for me.

This is what it feels like until you dive in. I was a late bloomer like you, and honestly felt like a little girl, absolutely out of place among adults with sexualities. The only way out of this was to put myself out there regardless, ignore that feeling, and allow myself to feel vulnerable. A lot of people are mentioning sex therapy and hiring a sex worker, etc, but that seems kind of counter-intuitive. You don't want to feel like you have to perform some special transaction or hire an expert just to do what you're trying to make feel natural for yourself. Online dating really is your answer. It might lead to your feeling confident enough to ask women on dates in the offline world.

But. Also know that if you're in it to get something out of it (ie. gotta have sex at all costs), you're either going to get hurt or hurt somebody else. If what you want is a real relationship, you should be in this with a generous heart, prepared to connect with another person. Maybe you should do more than just start dating. Maybe you should really explore yourself, your capacity to give, and what you want.
posted by Miss T.Horn at 10:07 AM on July 23, 2012 [4 favorites]


In your situation, you've got to ASK -- explicitly -- for everything you want.

If you see a woman (not a "girl") approximately your age, and you have talked to her for 5-10 minutes and find yourself attracted to her, then ASK for a date. Not to hang out, or to be e-penpals, but actually say "date".

If a date goes well and you both seem to hit it off, you can wait for the perfect moment of where she is in frame so you can slowly lean over to kiss each other....and maybe it will happen or maybe it won't. Or you can ASK her to come here and physically put her in proximity where you can kiss her.

If you are sitting with the woman in one of your living rooms on the third or fourth date, and it is 11 PM at night, and you are wondering, hmm....what next? Simply ASK her if she would like to go to the bedroom.

The magic spontaneous moments you see in movies sometimes happen, but don't wait for them or rack your brain for ways to artificially manufacture them. It is a much better strategy to ASK for what you want.
posted by 99percentfake at 10:17 AM on July 23, 2012 [1 favorite]


So... as a straight woman, over 30, fairly shy in romantic situations and drawn to fellow fairly shy people, I admit that I tend to wait for the guy to make the first non-platonic move. And wait. And (sometimes) wait. Thinking... "OK, kiss me now. Now. NOW." Which I'll readily admit, isn't terribly effective. But I think that if I were hanging out with a guy who told me, "I'm not hugely experienced, so sometimes I don't pick up on cues when I'm interested in someone and they're interested back..." I'd either 1) chat with you about how *I* tend to show interest [if I saw you as a friend] or 2) feel emboldened to smooch you, or 3) if I was feeling particularly shy but still interested, chat with you about how *I* tend to show interest and then proceed to do those things. A lot. That might be too subtle for your taste, but if you're anything like me, then I know subtle would feel less scary than coming out and saying, "Hi, let's go on a date!" Which... holy cow, I would faint if I had to say that to someone.
posted by pammeke at 10:17 AM on July 23, 2012


Although I agree that your talk about your standards (no dumb, dull, or ugly) sounds a bit callous, I also understand where that kind of sentiment comes from. It doesn't come from chauvinism or disdain, it comes from loneliness and a whole lot of confusion about what you deserve. Translated it means "I have waited so, so long to find someone and it is extremely important to me, and since my life's success rate in this area is a perfect zero percent, and I have no experience and especially no feedback about myself as a dating human, I am scared that the only people who will be able to like me will be people I am not attracted to."

Which is a legitimate feeling to have.

But whatever standards you construct for yourself in your mind will have no bearing at all once you find someone you have a connection with. Standards only describe surface features, both of a physical body and of a personality. The hottest and strongest fires start burning when you meet the human attached to the face and demeanor. All of the women I've had relationships with have been totally different from the kind of woman I have thought I would end up with.

You'll see. I thought I was picky too but I was just lonely and overthinking things.
posted by TheRedArmy at 10:18 AM on July 23, 2012 [9 favorites]


Oh, and for the record, the Big V thing wouldn't bother me particularly if I were interested in you. I was a late-bloomer myself and remember how much fun it was trying out new things.
posted by pammeke at 10:22 AM on July 23, 2012


Online dating is made for your situation.

Agreed. It's been a real boon for my introverted self, allowing me to do the asking/message writing at my initiative. It's also virtual, diminishing somewhat the panicky feeling of doing it in person. Once you've exchanged a few messages, suggest meeting up. Somewhere close to you, coffee perhaps. Unless the stars have aligned, she may not be the one, but it'll have been a first (and a nice cup of coffee).

It helps that you both have the same ultimate goal going in (dating), but also relatively little invested (if one party isn't feeling it, they can kindly demure a second date). After having gone through the process of e-asking out, meeting up, and mentally assessing things afterwards, I started to feel much more confident in my ability to, well, date. It also helped me start to hone what I'm really looking for in a partner/relationship.

Is it the most traditional, romantic way of meeting someone? Maybe not, but it's certainly worth a shot.
posted by Mr Yak at 10:46 AM on July 23, 2012 [1 favorite]


So you don't want to just hang out because it's too ambiguous, don't want to ask anyone out on a date because it's too anxiety-inducing, and don't want to do the losing-virginity thing only with a 'hooker' because you want some emotional connection, and on top of that you have "strict standards" about how intelligent, interesting, and at least somewhat attractive the woman in question should be.

I don't know if you realise it, but that sounds at best like you're putting yourself in a corner and ruling out all suggestions already. It's not clear what kind of advice you're looking for here, maybe like ead suggests above, start by separating all the things you're conflating, and ask for advice specifically on each of them? that may be more useful. Just a thought.

(btw again for what it's worth, I would disagree with anyone suggesting online dating based on this - maybe I'm the one not 'getting' online dating but I think it possibly adds more anxiety and insecurity to people already anxious and insecure, and, it offers a lot of room for bad faith or misguided communication if one is not managing to be honest and clear enough with themselves about their goals).
posted by bitteschoen at 11:00 AM on July 23, 2012 [2 favorites]


Seconding bitteschoen that you seem rather detached and ambivalent about actually having sex, and that you seem more hung up on its absence. Do you really want to have sex? Or is it just that you feel you are missing something? Are you really attracted to women? Do you feel that there is a sexual part of you? Do you masturbate? If so, what do you think about when you are? (Apologies if that is personal.)
posted by computech_apolloniajames at 11:18 AM on July 23, 2012


Honestly?

I think you need to ask yourself just what hump it is that you're trying to get over. If it was just losing your virginity, that'd be one thing. But even if you were to lose the BIG V tomorrow, it wouldn't change much, if at all. You got your dick wet. Great. So what? You'd still be the same guy you are today, with all the same worries and issues and everything else. And from reading your post, I'm getting this impression that you view yourself like you're some kind of a freak. Like a not-quite-fully-formed human being. Like an Other. In a sense, you're taking this label of yourself as a "virgin" and making it out to mean something about yourself, as if this label meant anything at all. It doesn't!

Believe it or not, being a virgin has nothing to do with your worth as a person. Plenty of people out there aren't fucking on the regular -- heck, some of them've yet to fuck at all -- and it doesn't change who they are. It's a completely natural thing to do, but if you haven't had sex yet, it's easy to blow the states of Having It or Not Having It out of proportion. But everyone does this sort of catastrophizing, even those for whom losing the big V is long behind them. So this feeling that you have now won't necessarily magically go away after you lose your virginity. It never really goes away. You won't be worrying about not having had sex anymore; instead, you'll be fretting over whether you're doing it enough. Or whether you're doing it with the right people. Or whatever.

Instead of getting hung up on arbitrary labels like 'virgin,' focus on getting to know people. Make it about them, not you. Remember that everybody has insecurities of their own. Focus on creating intimacy. And the sex will follow.

But the flip side, asking somebody on a "date," is almost even worse for me. I get that same, weird feeling--the mix of anxiety, embarrassment, and shyness. It's like a small child being caught somewhere they're not supposed to be. I feel like I have no place in the dating world--it's a completely foreign environment for me.

This is a GOOD feeling. I know that sounds like a weird thing to say, but believe me, I used to feel exactly the same way when I was younger. I'd feel like kind of an idiot whenever I was about to ask someone out. I'd feel like a fish out of water. In a way, I was -- I was way, way, way out of my comfort zone. But that's how you grow as a person -- by getting the hell out of your comfort zone. If you hear that voice in your head telling you that you're silly, that you'd be foolish to actually go through with this, take it as a sign that you're doing something right. Because you are.

While it'll take a lot of work, you can train yourself to work with that feeling, instead of against it. You'll be able to acknowledge that voice in your head, or the feeling, that's telling you that there's something wrong with you, or the way you're doing it, and just kind of set that voice off to the side, so you can get on with what you're trying to do, being confident that it's the right thing. She says no? Her loss. That's all you need to think about.

Awkwardness and inexperience is expected among 14 year olds. After 25, though, it's weird. It's expected that you've had a few experiences by 25, and if you haven't, it's twice-weird.

Well, once you have sex (and, yes, you WILL have sex!), you'll understand that awkwardness is pretty much the name of the game. I'm getting the impression from you that you have this image of you, as a sexual being, laying on the wrong side of the bell curve for sexual ability, with all the Casanovas and "regular people" on the right side. That absolutely isn't true. A lot of people out there, of both genders, are horrifyingly bad at sex, even if they've had a lot of sex before, and if you're going to be comparing yourself against them, you might want to keep that fact in mind. And just about everybody is terrible at sex the first time they do it with someone new -- that's just the way it is, so once you've found someone who you'd like to bone, and would like to bone you back, don't feel like you have to live up to some arbitrary standard, because there just isn't one. (Actually, there is one: being able to communicate with your partner. Bet you didn't have that in mind.)

Also, have you considered seeing a therapist? I know that's sort of generic advice that gets passed around here on the green, but I think it'd help for you to talk to a professional about how you feel, and to cast your feelings in a more normal light -- there are a lot of people out there in the same boat as you! Finally, please MeMail me if you want to get in touch, as there are some other things I'd like to have said, but I'm way too caffeinated to get them out of my brain.
posted by un petit cadeau at 11:52 AM on July 23, 2012 [6 favorites]


Just chiming in to agree that you should loosen your standards to explore the dating world. The only thing you should NEVER lower is an expectation of being treated with respect. You are right to hold standards - no one should feel like they have to put up with a bad relationship because you think you can't do better. However, those standards should be about being honest and respectful not hot and compliant.
posted by Gor-ella at 12:05 PM on July 23, 2012 [1 favorite]


(All this advice isn't good for much unless you have significant interest in being in a relationship, it's not clear to me that you do)

I think the most likely path to normalize your situation is to focus on getting into a relationship with long term potential. Get on some dating sites and let this become part of the personal current events you share with people, specifically, that you're experimenting with online dating, that you're interested in a potentially long term relationship, and that this is complicated by the fact that with one thing and another, strict parents and social discomfort as a youth, you've never been in a real relationship with long term potential. Obviously you don't have to get into the intimate details. If some nosy jerk presses you for specifics just say something like you never got past casual relationships that didn't go anywhere. If you don't want to really do internet dating you don't have to. The point is to get the basic fact that you are very inexperienced but relationship-minded on the table. I think your best bet is with someone who likes you, sees a potential future with you, and understands the true facts about your history and inexperience. Kissing is not rocket science, nor is sex for that matter. You just need a compassionate guide.

Like a lot of people (mostly younger though) online you seem to see relationships as a sort of game theory. My personal view is that this sort of "what's the winning strategy" thinking may be fine in college as a tactic for avoiding homework but honest and mature adults who are relationship-minded are looking for an honest connection, shared values, compatibility, the right one in a nutshell. For example, I don't believe there is any such thing as the "friend zone". In general people are interested or they aren't, occasionally they're not sure, but they generally know. Most of what people call the friend zone is just unrequited attraction. You're in the "friend zone" because they aren't interested in you that way and never will be. Another very real possibility is that they are interested or at least potentially interested but they can't figure out the signals from you. It's generally pretty easy to figure out: press for more intimate interaction in a conventionally date-y atmosphere, if they're not interested they'll demure, if they are they'll accept. Not it will not hold for 100% of situations but it works for the vast majority.

I will say there is a limit to how risk averse you can be if you want to enter the world of relationships. There's real emotional risks and they only get more pronounced the more serious you get. But in the initial phases a relationship-minded person who's into you and aware of your personal inexperience is probably your nearest bet. A person who's worth it relationship-wise will be willing to get past the oddness factor.
posted by nanojath at 12:11 PM on July 23, 2012 [5 favorites]


Everybody's giving good advice. I have a general tip. I have a friend (female) who picked up some palm reading, just as an excuse to flirt with and touch men she was interested in. You might find that an easy, flirty way to initiate physical contact and personal conversation. Plus, I personally find hand touching all sorts of intimate even though it's all very aboveboard and proper.

A woman who isn't interested in you will probably refuse to engage in palm reading shenanigans, but someone who does have a spark of interest will at least see it as an opportunity for a laugh or two and some touching.
posted by griselda at 1:04 PM on July 23, 2012


As nanojath goes, so goes my nation.

I think the single biggest factor in why you aren't getting dates is that you are not asking for them. You hang out with the object of your affections a lot in the hope that... she'll ask you on a date? If it's so big a risk that you can't be expected to take it, why would you expect her to? You're the one that wants the date.

That's like being the knight who sees the dragon and gets scareded and hides in the hope that the princess will slay it for him. Okay, gender stereotypes, but that's actually not what I'm talking about. If you display interest and she does notice it, but then you won't express it, it conveys that you are either not really that into her, or are into her but not enough to risk any emotional discomfort for her.

Not only is that a turnoff but it can suggest serious problems down the road. I've been thrown together with guys who had this courtship style, who I was not dating, for extended periods of time and their lack of willingness to have difficult conversations extended to more things than just romantic interest. It became very clear over time that if I had decided to help the shy boy out and do the asking, I would have ended up in the kind of relationship where you one day open a cupboard and two years of unpaid bills and a foreclosure notice pour out, because he didn't want to admit he'd lost his job. I also know that this guy broke up with his GF the same way he got together with her: first he didn't know how to ask her out so he sat there like a bump on a log until she figured out he was into her. Then he didn't know how to break up with her so he sat there like a bump on a log until she figured out she wasn't wanted and hadn't been for a while. It must have been extraordinarily painful for her to have been rejected in such a protracted, cruel way; but if this ever crossed his mind, he didn't show it. All he knew was that he was socially awkward and therefore it was her job to deal with it. Maybe my experience is unrepresentative, but consistently, the way a guy expresses romantic interest is the way he'll do everything.

I am sure you don't want to be that guy, so start by doing what he didn't.
posted by tel3path at 1:22 PM on July 23, 2012 [19 favorites]


It became very clear over time that if I had decided to help the shy boy out and do the asking, I would have ended up in the kind of relationship where you one day open a cupboard and two years of unpaid bills and a foreclosure notice pour out, because he didn't want to admit he'd lost his job.

So, so, so true. This why I won't do the asking for the first date, even though I am perfectly capable of doing so (but second dates and on, I'm more than happy to take action). I've learned it gets me someone who won't go out of his way to take risks for his own happiness/well being. I very much want someone who will actively pursue what is good for him, and by extension, the people he cares about.

Say you marry someone and down the line get really sick - you want someone who will get on the phone and harass the doctors for you, not someone who will ignore your situation because he is scared and hopes it'll get better without him engaging in reality.
posted by griselda at 1:38 PM on July 23, 2012 [9 favorites]


Third, if it comes to a situation wherein I'm competing with another guy for a girl's attention, I lose. More accurately, I concede. This has actually happened a couple of times in the last several weeks. I've been hanging out with a girl, and another guy starts showing some interest. The little voice in my head tells me that she's clearly going to be more interested in him, so I pull back, and tip my king. I don't know how to tell the other guy to fuck off, and, more importantly, I don't know how to convince myself that I should tell the other guy to fuck off.

You shouldn't tell the other guy to fuck off! Don't do that! That is not an effective way to get a date! This is bizarre and confused and wrong and makes me think that you have watched too many stupid movies!

Yes, in movies, men are always getting into fights over women. And the winner is always mysteriously Getting The Girl, as if her love was some sort of boxing trophy that was automatically awarded to the guy who won the fight.

In the real world, it doesn't work like that. I mean, if nothing else, imagine how you would feel. Suppose that two friends of yours started fighting with each other over your attention. (Imagine one dude friend of yours saying to another dude friend of yours, "Fuck off, he's mine," and then being like "Okay, Anonymous, now you have to be my friend and stop talking to Steve over there, because I won and he lost!") You'd probably think they were acting like idiots, right? Well, a lot of women feel the same way.

In general, this is a good rule of thumb: Women are people just like you, and dating is not fundamentally different from being golf buddies or study partners or part of the same book club or participating in any other human relationship. If you meet some guy and discover he has good taste in books and you want him to join your book club, what do you do? You ask him. You don't go around threatening all of his other literate friends in order to thin out the competition. You don't hang around him nonstop waiting for him to be all spontaneously "OMG I NEED TO BE IN A BOOK CLUB WITH YOU" without you ever mentioning it. You just say "Hey, we've got this book club thing, you should come along sometime," and either he says "yes" or he says "no," and that's all you need to do.

Dating is seriously the same way. It's not a prize which the cosmos awards you for exceptional manliness. It's not a boxing trophy. It's really just two human beings who decided to do a thing together because one of them asked and the other one said "yes."
posted by nebulawindphone at 3:42 PM on July 23, 2012 [12 favorites]


I'm a woman, and I'll tell you my take on your follow-up. You know what is totally compelling? It's when a guy is around me and I'm totally looking great and I think he notices but maybe not and then he kinda fumbles around and struggles with that...

same, weird feeling--the mix of anxiety, embarrassment, and shyness

...so that I know I'm looking so great, and I'm so witty that day that he's completely struck with me.

Just so you know, that's how it's taken many times. Whether you are embarrassed and shy because of inexperience or not.

Get on out there, tiger, and go ask a woman out.
posted by Houstonian at 4:06 PM on July 23, 2012


Also, the whole "friend-zone" thing? Total BS, at least in my totally anecdotal experience. Almost every woman I've dated started as a friend or an acquaintance. Being friends with a woman is not some dark pit you are stuck in -- it's just being friends with someone, which is awesome, and once in a great while something changes and the friendship turns into humping. (Mostly it doesn't, and it's super crappy and dishonest to pretend to be someone's friend in the hopes that they will one day see you and take off their pants.)

Just like with the whole competition with other guys thing that someone quoted above, this sounds like a vision of relationships based in movies, not in real life.
posted by Forktine at 4:18 PM on July 23, 2012 [4 favorites]


As someone else suggested - forget the "date" idea which is too intimidating and fraught with potential problems.
When I first went out with my husband it was a group thing to a Cubs game.
I arranged to next to him and, knowing he liked movies as I did, happened to just mention that a great, classic movie was going to be showing that week.
We decided to go see it together!! Voila!
Then, of course, we had to go out to dinner before the movie as we were both coming from work and then had delicious meal with a bottle of wine and then we went to our the movie ("The Searchers.")
Everything fell into place after that and we were married 6 months later - now its been 30 years and are still happy with one another. One first time activity I might add if I did the whole thing today - suggest going for a run together.
Just break it down to one baby step (as a group activity) then another - don't take on the whole thing at once.
Good luck.
posted by Tullyogallaghan at 5:01 PM on July 23, 2012 [2 favorites]


Oops - let me add for clarification that I "arranged to sit next to him."
posted by Tullyogallaghan at 5:02 PM on July 23, 2012


Online dating. It won't be magic at first. It will take time. I have a friend very similar to you and he was 27/28 before his first date. Now he has a great girlfriend! They met online.

Take chances and risks everywhere. Not just with women, but in everything. Get used to pushing yourself a little bit out of your comfort zone.
posted by manicure12 at 8:20 PM on July 23, 2012


Online dating may not be the long term solution to you, but it may get you started.

If I were you, I would make a profile and then make yourself go on three first dates in the next month. Have nice and low expectations -- if the dates suck, no obligation to go on a second one and if all three dates suck no obligation to keep doing it.

But even if they all suck, it might help break down the wall you've built in your mind. And you never know, you might actually end up having fun.
posted by no regrets, coyote at 10:29 AM on July 24, 2012 [1 favorite]


I require a woman...

This is not a good starting point for you if you're wanting to meet people and start relationships. I'm not saying it's something you can/should change, I'm just saying that there are a lot of great people out there and some of them may not meet all of your criteria to the level that you 'require' them to. The thing is that you'll never know because you'll never get past acquaintance phase because you've already vetoed them.
posted by RolandOfEld at 11:43 AM on July 24, 2012


I found (at age 25) that there is no "normal" people anymore... everyone is just unique, and when you're actually in a relationship with someone, you learn that they are very unique. Every single person is different, and so are you. So the fact you're inexperienced is just one quality you have, although you have many many other qualities.

Throw it out of your head that you're a virgin, and also throw out any fear of rejection, ridicule, or care of what others think about you. After all, you sound like a cool dude, you're 30 and fairly happy with yourself and work in the service industry. As cliche as it sounds you have to be yourself. Everyone I worked with in restaurants were cool as hell, sounds like you have a good social circle (around your job?) so lots of opportunity. What I would do, is forget about sex, and realize that alot of women you want to be with are in a position right now where they have dated a bunch of jerks and A-holes and want to date a nice, down to earth, manipulative dude. I read countless tales on here of women who can't figure out how to date the right guys... they're all looking for a guy like you describe yourself. Your ONLY problem is the way you shoot yourself in the foot and hold yourself back, to which I would prescribe alcohol (specifically tequila), but I'm no doctor.

Think of it this way, when you "concede" to another guy. Put yourself in the woman's shoes... does she want to date someone who knows how to shmooze a woman, knows what to say to get in her pants, knows how to manipulate her emotions, and knows how to cheat on her or dump her when another skirt catches his eye? Or does she want to date you, a nice honest guy who is the perfect boyfriend, who just has one little quirk, that he has no experience in relationships? Experience can be a dual-edged sword... I constantly have to stop myself from comparing my current relationship to previous (shitty) relationships, because my current one is awesome and not shitty at all. Essentially once you have a bunch of crap relationships under your belt, you have to consciously not allow them to fuck up your next one. You dont have that problem!
posted by el_yucateco at 1:04 PM on July 24, 2012 [3 favorites]


Wow. Seriously, thanks to everybody who has taken time to help me out here, and via memail.

I'll try to respond to some of the comments:

Seems like people just pick someone nearby that they kind of like, then focus on getting into some sort of interaction, THEN focus on getting to hand-holding, and only THEN think about maybe a kiss, etc. What if you put sex (or even making out) off the table altogether for now, and just set yourself the immediate goal of getting a woman one-on-one in some sort of romantic context?

The problem is that I've been there. It's just that I have, literally, no damned idea what I'm supposed to do in that situation. When I was in college, I wound up with a friend of mine, in her dorm room, in her bed, and somehow I froze and wound up leaving. It was so mind-boggling that she sent me a text message the next morning saying, "Wow, you're an idiot."

I'm not quite sure what kind of experience you are looking for but I find it concerning that you would ask 'How do I get past this?', is that what you want, to get past it? The whole relationship thing is meant to be enjoyable, it doesn't sound like you expect to enjoy it too much if you want to just get it done so you can tick a box. You don't have to conform to an arbitrary social norm however pervasive it may be if you don't actually want to.

It's not that I want to get past it for sake of getting past it. I want to get past it because I feel like it's getting in the way of my future success. Once I don't have my lack of experience hanging over my head, I feel like it will be easier to get more experience. It's getting past that first hump (probably a poor choice of words) that seems to be a major obstacle.

Would you consider retaining a sex coach (subset of sex therapy) to help you gain a little experience with constructive feedback? They are skilled at working with novices in a caring and nonjudgmental way, both on "the mechanics" of how to kiss, touch, etc. as well as the interpersonal dynamics of flirting, reading nonverbal signals, etc.

I'm not entirely sure what a sex coach is, but it seems like an interesting idea. How does one find more information?

What I notice very clearly here is your use of the passive and impersonal - "an emotion that is so widely discussed, written about, desired, and craved"... by? "widely", ie. by other people, not by you? You are posting this, but you don't sound a bit like you actually desire and crave a sexual relationship with a woman, the sex in itself or the emotional connection and all that. You say you are "concerned" about your development being "deficient". This is language that sounds very unemotional for such an intimate issue. It goes through your whole post, this sort of emotional distance and remove. This and your list of qualities and the fact you clarify you're happy enough alone and the list of caveats and "high standards"... it all gives an impression of something you're sort of pondering and considering from a theoretical perspective only, or from the point of view of thinking only about the absence of this experience as a piece of an otherwise perfect puzzle.

I very much do want to have sex, and have a relationship, and all the accompanying steps along the way. I think that tone came across because I don't have any body of experience from which to write. It's like saying "I guess I'd like to fly the space shuttle, everybody says it's pretty cool" but I've never even been in a Cessna.

Several people mentioned visiting a prostitute. Like I said in my original post, this is entirely out of the question. It's not for any moral reason, or anything like that. The reason that I won't entertain the idea is that I'm pretty sure it would make the self-confidence issues worse. That is, I'd tell myself that the only way I could get laid was to pay for it (which, by the way, would be an entirely accurate representation of the facts).

Seconding bitteschoen that you seem rather detached and ambivalent about actually having sex, and that you seem more hung up on its absence. Do you really want to have sex? Or is it just that you feel you are missing something? Are you really attracted to women? Do you feel that there is a sexual part of you? Do you masturbate? If so, what do you think about when you are? (Apologies if that is personal.)

I think it's a combination of the two. I definitely want to have sex. I masturbate and fantasize regularly, and I imagine I'd certainly enjoy it more with a woman. But I also am hung up on its absence. I'm concerned that I'm going to meet somebody that I'm really into sometime in the future, but I'm going to be too paralyzed to make anything of it. I worried that my lack of experience is going to get in the way of my happiness some time in the future.

You shouldn't tell the other guy to fuck off! Don't do that! That is not an effective way to get a date! This is bizarre and confused and wrong and makes me think that you have watched too many stupid movies!

Yes, in movies, men are always getting into fights over women. And the winner is always mysteriously Getting The Girl, as if her love was some sort of boxing trophy that was automatically awarded to the guy who won the fight.


I should have clarified this point. I'm not talking about a situation where a woman is hanging out with different people at different times. There have been, in the last several weeks, a couple of instances where I have been hanging out with a woman, and another guy has come over to our table and started hitting on her. I feel like this is tremendously disrespectful, and it's completely acceptable to tell the guy to fuck off in this kind of situation. But I never do, because the voice that kills my self-confidence always reminds me that she would rather be with him anyway.
posted by ann on a mouse at 12:39 AM on July 25, 2012


I should have clarified this point. I'm not talking about a situation where a woman is hanging out with different people at different times. There have been, in the last several weeks, a couple of instances where I have been hanging out with a woman, and another guy has come over to our table and started hitting on her. I feel like this is tremendously disrespectful, and it's completely acceptable to tell the guy to fuck off in this kind of situation. But I never do, because the voice that kills my self-confidence always reminds me that she would rather be with him anyway.

No, that doesn't change anything.

Again, it might help to imagine how you'd feel if the genders were switched. Suppose you and Steve are out having dinner, and a cute girl at the next table starts flirting with Steve. Would you be like "Fuck off, cute girl! Steve is my friend! You are not allowed to flirt with him"? That would be weird and creepy and controlling, right? In fact, it would be pretty damn disrespectful to Steve if you responded that way, right? After all, Steve is a grownup, and he's perfectly capable of deciding for himself whether he wants to flirt with this girl or not. If he wants her to go away, he'll tell her to go away, right?

Well, okay, if it's weird and controlling and disrespectful to treat a male friend that way, then it's just as weird and controlling and disrespectful and so on if you treat a female friend of yours that way.

In fact, it's not just a matter of "weird" or "disrespectful." This sort of behavior is actually a major red flag for domestic violence. If you look at articles about domestic abuse, or lists of warning signs, one of the questions is usually something like "Does he try to control who you talk to?" or "Does he get angry when you talk to other men?" Because statistically speaking, that sort of controlling attitude tends to go hand-in-hand with outright physical and emotional abuse. Now, I'm not saying you are the sort of guy who would beat his girlfriend. But if you start acting all territorial around your female friends, trying to prevent men from talking to them or flirting with them when you're around, you are going to make yourself look like a potential abuser. Your friends are going to look at that behavior and think "Oh, jeez, that's a bad sign. I would never get involved with a guy who acts that way." Which is sort of the opposite of what you're trying to go for here, right?

There's one exception to all this. If your friend has already told a guy to fuck off, and he isn't listening, you're allowed to back her up. ("Dude, she asked you to leave her alone. I think you should go now.") But the crucial thing here is that in this sort of situation, you're respecting her right to make her own decisions, and supporting the decision she makes. You're not deciding for her that she can't talk to this guy. You're just standing up for her once she's decided.

Anyway, this is sounding more negative than it really needs to, and I'm sorry about that. My point is actually a positive one. Here you're all beating yourself up for not being "assertive" enough or whatever. But actually, it sounds like you're doing exactly the right thing, and the "assertive" stuff that you're thinking about doing would in fact be a huge mistake. So quit beating yourself up! On this issue, you're doing the right thing after all! Keep up the good work!
posted by nebulawindphone at 2:06 AM on July 25, 2012 [1 favorite]


Again: internet dating will bring some clarity. And on top of that, I think you would benefit enormously from some therapy because it sounds like your self-confidence issue is really getting in the way of your ability to form connections.
posted by DarlingBri at 4:20 AM on July 25, 2012 [1 favorite]


I'm not entirely sure what a sex coach is, but it seems like an interesting idea. How does one find more information?

I think you need a dating coach more than you need a sexual coach (or sexual surrogate) -- googling that term brings up a gazillion sites, and I've seen articles about dating coaches in the New York Times and other mainstream places, so it's not like you are out in crazy land here, either. No one would think it odd to pay for professional coaching if you wanted to be better at rock climbing, right? So why not pay for guidance on a skill that is important to you?

I'm saying you need a dating coach rather than a sex coach, because your real issue is in meeting and dating people; you aren't getting far enough for sex to become a real issue.

I should have clarified this point. I'm not talking about a situation where a woman is hanging out with different people at different times. There have been, in the last several weeks, a couple of instances where I have been hanging out with a woman, and another guy has come over to our table and started hitting on her. I feel like this is tremendously disrespectful, and it's completely acceptable to tell the guy to fuck off in this kind of situation. But I never do, because the voice that kills my self-confidence always reminds me that she would rather be with him anyway.

I couldn't agree more with nebulawindphone's comments above about this. If I am out at a bar with a female friend, it is not rude or weird or whatever for a guy to flirt with her -- part of why she is feeling safe enough to flirt with a total stranger in a room full of drunk people is that I'm with her and she knows I have her back and will help her shut down anything that make her uncomfortable. Once in a while I'll be out with my wife and dudes will try and hit on her; she either shuts them down herself or signals me and I gently let them know it's not happening. And that's not a big deal, either.

If this is happening when you are out with a platonic friend, I'd say this is normal and not to even worry about. But if it is happening when you are on a date, and the women are routinely flirting with and maybe even leaving with the other guys, the issue here is you -- do the women not know this is a date? Are they wanting to escape and are using the other guys as a way out? Something not quite right is going on, and getting territorial is not the right response.
posted by Forktine at 5:51 AM on July 25, 2012 [2 favorites]


Hi!

I am a woman that likes men. It makes me sad that you feel this way- because from your brief writing here I can tell that you are TOTALLY NORMAL AND FINE AND NOT A WEIRDO.

You don't have to change anything about yourself to get the results you want - you just have to get over the paralyzing fear of expressing it.

In the situations where you feel scared and anxious, try to think - what is the WORST thing that could happen- and how likely is that thing to happen? In most romantic situations, even if you completely FAIL, it will not be so mortifying as to ruin your day or life or chances of future sex.

Sex is awkward and strange and hilarious by definition. I know that it's easier said than done, but you need to loosen up and relax about it. This holds true for everything from the expressing interest to the physical stuff down the road. Even if you screw up, having a relaxed easy-going attitude makes you TOTALLY ATTRACTIVE to women and give you a leg up on other guys, despite experience level.

Your lack of experience is really not the problem that you think it is- your lack of confidence is what's hurting you. Tell the 14 year old voice in your head to shut up and remember that you are a successful, happy, awesome, grown ass man who has done lots of cool shit with his life and has a lot to offer a woman, in and out of bed.
posted by sarahnicolesays at 10:45 AM on July 31, 2012


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