This is going to sound lamer than lame, but I'm in my thirties and not only have I not had sex yet, I haven't had a girlfriend yet. To be fair to myself, my mother passed away when I was six, I've suffered some sexual and other abuse which I've dealt with and put on the shelf, and I've battled back a long way from mental illness (schizoaffective). I'm very functional. Aside from being a little overweight, I'm not bad looking. And I know I've got the rest of the package—I'm smart and funny, I care, I wouldn't think twice about dancing with or singing for my woman, and I'm pretty sure I know just how to touch a woman. I just can't seem to pull the trigger when it comes to asking out the women I like. I also kinda feel like I might get stuck with the first one. I really lack confidence and those kinds of social skills. If I could ever hook a woman, there'd be no going back for her, I promise you! I'd lavish her and ravish her! Do you have any advice for me? Oh, and another thing, how do you tell a woman (or hide from a woman—though I'd prefer not to) that you haven't had sex before without her laughing at you and telling all her friends? I figure my lack of experience is going to give me away in any event.
It sounds like you are asking me three different questions. One is, how do you ask a girl out? Two is, how do you behave during your very first sexual encounter? And three is, how do you prevent a first date from turning into a long-term, committed relationship before you've had a chance to get to know each other and make sure that's appropriate? (If I've missed anything, feel free to write back! Frequent flyers are welcome.)
It's hard for me to give you advice about question number one because I don't know how much social experience you have at the pre-dating level. Would you feel comfortable asking a friend at work to go out for a drink and some bar snacks when your shift is over? Do you have people you go out with to movies, poetry readings, or concerts? What are your own hobbies and recreational favorites? Developing these things are an important prerequisite to dating. First you need to be able to just identify an activity that you and others might enjoy and invite everyone to participate. Having friends is important because they are your first refuge if you get shot down asking somebody out on a date. Friendship can also help you to understand what type of people you like spending time with; how to tell who is a compassionate person instead of a selfish, critical ass; and what you need on an emotional level from a partner.
But when the moment comes to date, there's no substitute for just gathering up your courage and stammering out the invitation. Basically, a guy has to want to go out with a woman so much that he's willing to risk the gut-wrenching devastation of having her say, "Oh, gee, I need to stay home and wash my hair." The whole issue of rejection is complicated by the fact that sometimes when women say no, they don't mean, "I hate you and wouldn't be seen dead in public with you," they sometimes really do mean, "I have to stay home and wash my hair. But I'd love to go out with you on another occasion."
This is how I handle it. First of all, I try to pick an activity that I would enjoy even if my crush says no. There's no point in going on a date to the opera if you're going to be yawning through the whole thing. Say, "There's this great review of a restaurant, would you like to check it out with me?" Or, "I've been dying to see this museum exhibit." If she says, "Me too," ask her to go with you. If my crush says no, I wait to see whether he or she will say, "But I'd love to go out sometime," or "Could we go on Friday instead of Thursday?" If I don't get an obvious positive response like that, I say, "Well, I'd love to be able to spend some time getting to know you better. If you ever want to get together, give me a call." Then I really do leave it up to them to call me. You don't want to be a pest or a stalker. I don't invite the same person out more than twice. If they say no both times, I assume it's just not the right time.
Rejection feels shaming. It makes you feel like you should never have been born. But that isn't really what it means. Rejection can be arbitrary. Maybe they already have a partner, maybe they are in such a fucked-up place emotionally that they don't want to date right now. Maybe they know something about themselves that makes the two of you a very bad match. Whenever I've forcefully pursued someone and insisted that they go out with me, it's been a bad, bad mistake. Rejection is nature's way of telling you to lick your wounds, get over it as fast as you can, and focus on somebody else. Sometimes you make a mistake that you can learn from the next time you try to hook up. But that's all it is—a mistake. My heart goes out to you because I know how hard it is to take this advice. But save this paragraph to re-read. You may imagine that you'll feel bad for the rest of your life if the first girl you ask out turns you down. But you'll probably just feel bad for a couple of days.
The other things to remember is that all of us, every single man on the face of the earth except Brad Pitt and a few porn stars, get turned down the majority of the time. Yes, that is the unpleasant truth. As you get more experience, you learn to place less of an investment on the initial invitation to grow closer. You get over rejection more quickly. You also get better at pre-screening people to see who might be ideal and who's a surefire dud. I'm not a ten when it comes to personal appearance, so I don't try to date tens. (If they ask me out, however, I'm not stupid enough to say no.) But that's not just about low self-esteem, it's about the fact that when it comes to sex and intimacy, I am more attracted to people who have a sense of humor, a spiritual life, and an imagination than I am to beauty all by itself. But it took about twenty years to get here, so don't be too hard on yourself if you don't figure this all out at once.
Question number two: How do you behave during your very first sexual encounter? I guess we'd all like to be bigshot experts between the sheets. We'd all like to be studs who can send our partners up a wall without a second thought. But sex is, in real life, somewhat messy, unpredictable, and awkward. Even if you've had sex with a hundred girls, you need to ask each woman about her own body and needs. Women's sexuality varies a lot, partly because they've got a hormonal cycle that makes their bodies and emotions change more over the course of a month than yours will. The oral sex technique that made her come yesterday might irritate hell out of her tomorrow. So calm down and give yourself permission to ask questions.
I definitely would not pick somebody to have sex with who seems bitchy or competitive. You want someone you feel safe with, because I think you really do need to tell her it's your first time. The good news is that some, if not most, women will not look down on you for this fact. She might and probably will take it as a sort of sacred mission to show you how wonderful sex can be. If she wants to take the lead, let her. The best lovers are men who've had the good fortune to run into articulate and assertive women who weren't afraid to say, "Do this like that right now, mister."
Before you have sex with anybody, take a massage class. This is a good way to learn about human anatomy and get feedback about the quality of your touch. It's also damned good foreplay. Focus on her whole body. Don't rush into intercourse. The first time you are sexual with someone, it's okay to avoid intercourse, in fact. You want to be able to savor the first kiss, the first time you see or touch her breasts, the first time she caresses your neck and shoulders. Making out is, I think, even more important than the penis-in-vagina contact.
Buy some condoms and use them when you jack off. Get used to the way it feels to touch your own dick when you've got a rubber on. You can teach yourself to be able to keep it up and even come when you are wearing a condom. That's a very important skill to have during sex with a new partner.
Other than that—just keep breathing. Nature wants you to be able to have sex. You have several million years of human evolution behind you.
On question number three, I had to laugh because this is a mistake that so many of us make. All I can say is, slow yourself down. Be conscious and deliberate about entering a relationship. Even if you are lucky enough to meet the love of your life on your first date, don't cheat yourselves out of all of the wonderful phases that a relationship goes through as it unfolds.
And remember that one date does not obligate you to abstain from dating anyone else. Nor do you have to engage in sex on the first date. Do what you've been doing your whole life—identify a problem, study it, gather information, then when you feel ready, try out new behavior. The rewards are so great that I'm wishing you the best of luck with creating a new phase in your life.