Lose your Virginity

First, you have to think about your motivations for wanting to lose your virginity. If your goal is to simply check off the "Had Sex" box on your life list, or to gain respect from others (or even yourself), you should probably reconsider. Let me be perfectly blunt: there is nothing wrong with being a virgin. As long as you're comfortable with that state of being, most people will respect you for it (and the rest are probably jerks anyways). Losing your virginity will not change your life, make you a man, or complete you as a person. The vagina is not a mystical portal into adulthood. If you expect it to be, you're setting yourself up for a letdown.

There are good reasons for wanting to lose your virginity, though. Sex is a wonderful experience that can enrich your life, bond you to your partner, and create lifelong memories. It can also ruin your health, turn you into an emotional wreck, or saddle you with steep financial obligations, so the standard caveats about safe sex apply.

Who Are You?

There is no one-size-fits-all advice for this subject, and I am not a professional anything, so take any advice in this article with a grain of salt. But in formulating your plans, be careful to take into account your own personality and background.

Take the Long View

Especially if you're young--and by young, I mean "under twenty"--you should probably be less focused on creating opportunities for yourself right now, and more focused on turning yourself into the kind of person who will make an attractive sexual partner down the road. There are lots of ways to do this, and you should look for one which appeals to you. First, work on your physical appearance until you're comfortable with it. Work out regularly, practice good personal hygiene (smells are an especially huge turn-off), lay off the junk food. If your wardrobe is too threadbare, you should make some improvements. If you stumble all over yourself talking to women, or are afraid to show interest in women, then work on those things as well.

Just remember that your goal should be to focus on your weaknesses. You're not trying to become a bodybuilder, a fashion plate, or a silver-tongued seducer. You're just trying to smooth off the sharp corners that might cause some large fraction of women to reject you before letting themselves get to know you any better.

Next, think about the sort of woman you want to appeal to. Is she intelligent? Funny? Physically active? Musical? A lit geek? However broad or specific your tastes may be, you should start hanging out at the sort of places where that type of person tends to congregate. Go by yourself or with friends, but don't necessarily go there to meet women. For example, if your intention is to know the love of a lit geek (c'mon, you know the glasses only make them look hot), you should be working to expand your knowledge of literature. Read Shakespeare, take in plays, spend time at the library.

I think this advice works because people are attracted to people who are like them in some way. If you don't have any particularly fond feelings for the written word, then you're probably not going to be jonesing for English majors in the first place. So you'll be doing something that you like, and expanding your horizons, even as you work to make yourself more attractive to the women who attract you.

Big caveat: Don't tell yourself, "I want a gamer girl!" and then spend hours and hours "improving yourself" in front of the Playstation. I believe that men have a tendency towards obsessiveness, while women generally prefer a more well-rounded approach to life. Maybe it's because men are more competitive, and competing successfully in one area of life requires that sacrifices be made in other areas. So even if you go to a LAN party to meet the handful of women, try to impress them with your looks, your personality, your willingness to offer constructive advice without being patronizing. Don't try to impress them with the number of games you own, or your frag count. The fact that you showed up to the party means that you and she share an interest in gaming. She's already checked off that box, and is now evaluating you in other terms.

Again, the goal isn't to convince women to sleep with you. The goal is to convince them that you're the sort of person they would want to sleep with. Patience is critical. This isn't what you want to hear, I know. You want to know how to seduce a woman within the next two days or so. Sorry, I don't have an answer for that. I think it's a huge mistake to try to shortcut this route. Desperation shows, and it's never attractive.

That Special Night

Patience is still critical once you've attracted a potential partner. She's going to have concerns about you, about sex, about making it special. So are you. It's probably best to let her know ahead of time that it will be your first time, so that her expectations are well matched to the situation. Like I said, you should be confident about your virginal status, even if you would like to change it. Your partner shouldn't be turned off by it. Some may even be excited at the chance to deflower you.

It's ideal if you've had laid-back, wide-ranging discussions about sex, so that you're aware of her biggest fears and turn-ons. That sort of knowledge will give you a better idea of how you want to approach your first time, and that will give you confidence. Don't worry: most people find sex an inherently interesting subject, and will want to talk about it at length. It's absolutely critical that you discuss birth control as part of these talks, and make all those preparations for when you take the plunge.

Since this will be your first time, you should be willing to let a plan fail. It doesn't matter how much preparation it took, or how much the room cost, or how much time you spent hand crafting your own bondage gear. If the plan isn't turning out well, it's better to back off and try again later. For example, it might sound fun to make love under the stars. But by the time you're out there and it's too cold and you can't find anywhere flat to lay out and the mosquitos are just merciless... scrap it. Try again next weekend, and this time check into a hotel.