There are three basic ideas to keep in mind:
- You are far from the first person to flirt with her.
- Flirting with a woman is just as much about deciding if you want to sleep with her as it is talking yourself up.
- Hooking up is generally a good idea if you want each other and you’ve established enough mutual comfort and trust to be invested in conversation after sex.
So why should you actually want to sleep with someone?
I have my own answers: because it’s exciting to have to pitch myself to a cute girl who makes me giddy and nervous, to gain her trust and do so by offering mine. It’s fun to be goofy with someone I don’t know, get each other off, and see what happens when we’re both open and honest. To feel suspense and release at every point in the evening, from the start of conversation to the hesitation and enthusiasm of a first kiss to the walk to her place when we both all but know that we’re going to fuck and get to feel smug about ourselves. Above all, good sex is fun.
Hooking up is people tourism, in the words of someone with whom I have hooked up. You can go for it when you’re lonely, when you feel cocky, to make a good story with someone you wouldn’t otherwise meet, or for the sheer joy of recklessly getting to know someone else. You’d be amazed the things you can learn from someone else (or, frankly, about yourself) in bed, and how much another person in your bed can enrich your life. It’s also astonishing how frequently a good, memorable one-night stand can lead to a great friendship or relationship, or even useful professional connections.
As a dude who writes about sex, I bring up sex when I’m hitting on a woman because it’s one of the things about which I care and have strong opinions. And not every woman is into that, which helps me figure out our compatibility. If she is, the transition to physical contact is a lot less daunting and unpredictable, because she’s probably already imagined having sex with me. Even if you don’t write about sex, you should learn how to have a productive, safe, titillating conversation about sex with people to whom you are attracted — and how to end it quickly if she doesn’t want to have that conversation.
You should be able to explain to a woman why you want to sleep with her, in a way that neither apologizes for what you want nor disrespects her wishes — and more importantly, in a way that makes her feel safe. The point is not to make you feel awful about being a man or responsible for shitty things other people do. You should try to understand what it’s like to be a woman on the receiving end if you’re going to flirt with women. Understanding her frame of reference for a potential evening with you is one way to help ensure you both have a good time.
I like to think of straight “hookup culture” as a particularly tragic tragedy of the commons. For a variety of reasons, including popular culture, patriarchy, and perhaps biology, men make the advances. Men want to sleep with women to prove they’re not losers — usually to other men, and the more attractive the woman, the more impressive the conquest.
I know, I’m generalizing. But enough men buy into that system that it becomes everybody’s problem. If, theoretically, women are only really good for proving you’re a real man and can be ranked on a scale from 1 to 10, figuratively nothing else matters. Someone who believes that will use every trick in The Game and hit on every woman in a bar until one says yes. Hopefully they care about consent, too, but too many do not. If they sleep with someone not subjectively attractive, they’ll say how many beers they had first before telling their bros. Even if not every guy does this, enough do that most of the time when a man is hitting on a woman, he’s doing it to be able to tell the guys about it later.
You’ve probably heard of the term “negging,” or insulting a woman you’ve just met to make her eager to impress you. Regardless of its morality (but for the record, it’s a shitty thing to do), people do it because it works. Women are people and, in general, people want to be liked, and they’re willing to work to be liked. But mostly, women want to talk to a guy who hasn’t gotten all the information he needs to decide to sleep with them before actually talking. Negging is a way of tricking someone into thinking that you haven’t made up your mind yet. This problem disappears if you genuinely need more information than how they look and what they choose to wear to sleep with someone.
The real tragedy of this is, in my experience, women have sex drives that are roughly equivalent to men’s. Women just have far less freedom, encouragement — or even safety — to express it. They’re more easily pigeonholed by their sex life, as many people are unwilling to believe there’s a whole continuum of women between sluts and virgins. By virtue of a woman’s existence and the appallingly common potential misfortune to experience sexual assault, society dictates that women must be skeptical of potential partners. But making someone feel safe isn’t just a good idea if you want to get laid. Showing a woman that she can feel safe with men and trust men is one of the most rewarding things you can do.
If you skimmed through everything above, you either don’t need to listen to me or you don’t get the point. Because here’s the thing:
There is no formula for creating enriching experiences with strangers. The vast majority of those experiences will not involve sex.
If you lack the courage to talk to women, you should fix that with practice, for no other reason than because you’re not incorporating half of the world’s population in your life. (If this is the case, you should do that before you think of sleeping with women — and maybe take a break from porn.) It’s far more likely that such a person could learn something life changing today from a woman in conversation than in bed.
To some extent, everyone wants to feel intimate, have sex, and be loved. That’s why sex happens so often, in spite of rampant cynicism, lack of curiosity and humility, and disrespect all sexes experience constantly. I want everyone to be lucky enough to experience a genuine physical connection with another person — to be intoxicated by another living, breathing human, around whom you would feel self-conscious were that impulse not an impediment to one of the most immediate and sincere ways you can show and experience affection.
Trying to write a script that goes beyond basic courtesy and common sense will only limit your next beautiful adventure.