What's a boy to do?

My attempts at flirting with women tend to be received as friendliness. How can I convince them I mean business?

Published May 9, 2003 7:38PM (EDT)

Dear Cary,

I was reading a column you wrote where you asked one of your advisees if the guy she was interested in was drawn to her in an electromagnetic-type way. Viewed in this way, it seems that almost no women (save for one) have ever really been attracted to me. Granted, I am on the young side (21), but it seems odd that I would be so unattractive. While I could stand to lose some weight or work out more often, I am by no means ugly.

The thing that really perplexes me is that I do so well with women just as friends. I have no trouble talking to women, and I tend to connect with them very easily. I'm not underestimating myself nor misreading the situation and thinking that girls who really want me romantically are only interested in friendship -- if anything I'm apt to let wishful thinking get the better of me and false positive. How is it then, that I can be so attractive to women just as a friend, but unattractive as a boyfriend? Are love and friendship that different? Or do women just prefer assholes? Is it because they're turned off by someone who relates to them as a human being and not a piece of ass? Am I really ugly and don't realize it?

I complained about this to a friend once and she suggested that it might be because I'm not flirty enough. I'll admit, I'm not a huge flirt, but I don't think I'm that bad at it. I just feel like my attempts at flirtation are received simply as friendliness.

Another thing, I know an effective way to flirt is through touch, but I'm uncomfortable touching people unless I have a really close relationship with them. In fact, the only people I've had a relationship with whom I've been comfortable enough to touch them spontaneously are my little brother and my last girlfriend. Is touching that essential to flirting? If so, then I'm in a Catch-22, because I can't touch someone comfortably unless I'm in a relationship with them, but I can't get into a relationship without touching them.

What Is a Boy to Do?

Dear Boy,

If your attempts at flirtation are being received as mere friendliness, maybe you're not really flirting. Flirting is friendly but with an edge of aggression; what you're trying to get across is that this may seem very casual out here in public and we're just having a few laughs but if I ever get you alone you won't be chuckling.

Try making it a little more obvious. If touching doesn't work for you, use words. Heck, why not suggest she should come over and take her clothes off and get in bed with you and spend the night at your house? At least, she'll know you're not just being friendly.

But then maybe that shows how little I really know about flirting.

I am not a great flirter. I come from a family of nontouchers. We are not big on light, evocative small talk. We have trouble focusing. We are basically frightened of other humans. But if there is one thing my family does seem to have bequeathed me and my siblings it is a fierce, idiotic persistence in the face of monstrous odds. If I have had any success with women it has been due more to a kind of preternatural audacity (fueled, in the early years, of course, by copious drafts of liquid courage) than to anything you could call charm.

The one thing I did discover, however, during those years when I was attempting to learn how to signal interest, engage the other and close the deal quickly so that another night would not be spent lying under the sheets wondering why I never went to Princeton, was some mental trick that I believe actors must have a word for. I don't have a word for it. But it involves singular belief and focus. It involves slowing down and moving slightly in, just enough so that you are no longer just a guy in the room but you are really there.

Around every romantic target, envision a series of concentric security zones; the outermost area is for store clerks and bankers; inside that is the area for same-sex friends and fathers; and inside that, I postulate, is a narrow band of flirtatious airspace that, were it possible, would be guarded by infrared sensors and dobermans. If you can map and occupy that space you are well on your way toward signaling that you don't give a damn if you never went to Princeton, tonight's the night.

When you get to that space, you will know it, because you will feel a nearly irresistible urge to either kiss her neck or run to the valet for your keys. You are now in the area of the tipping point. Stay there. She will probably be holding her ground heroically, wondering if you're serious, wondering how long it's going to last. Stay there just long enough so she knows you're serious. Don't stay there so long that she begins to think you may have thrown out your back. Then pluck the olive out of her martini and say, "Were you going to eat this, or shall I?"

If she's not drinking a martini, you're going to have to improvise. You have to do this smoothly, with confidence. Remember: You're in her zone. Being in there is like being in her bedroom with your clothes off. You cannot afford to look ridiculous. You have to hold your own. And you have to act fast. You have to do something while you're in there that she will remember. Damn. I can't think of anything. Oh, quick, quick, quick, think of something. You've only got three seconds before she spots her girlfriend across the room and waves. Quick! Quick! Her buttons! Her shoes! What does her father do for a living? Does she have a leopard-skin purse? Are her eyes the color of a blueberry jellybean? Is her nose like a little button? Does she have a mane of hair you'd like to see on a palomino? Are horse references good or bad? Is her hair too close to her face to make a horse reference? Is making a horse reference confusing the issue of who will be the rider and who will be the horse?

Sorry. That was the buzzer. You're out of time. You're going to have to practice. But that's OK. The only way you can practice is to keep going in there. If you say something that strikes her, you will know it, because she may nod and move even closer in barely perceptible surrender.

The only other thing I can remember about flirting is a certain actorly attention to posture and rhythm, a way of harmonizing kinetically with her movements, so that you seem to be in natural sync. This is important, because what you are trying to achieve, ultimately, is just such a physical melding. If you seem awkward around her, unless it is the endearing awkwardness that is the stuff of romantic comedies, she will not feel like falling backward into your arms. However, if you attend to gracefulness and sculptural presence, if you make of yourself a kind of effortless dancer around her, you can achieve the special kind of warm, pleasant hypnosis that leads seamlessly to breakfast.

Actually, now that I am thinking about it, there are two other approaches: the insolent slouch of junkie indifference, and "You are my sister."

The insolent slouch of junkie indifference is a posture that is sly, slow, apparently uncaring and nearly asleep, but you know it works because I know you have seen this happen: At a certain point at a party you see a gorgeous slinky blonde in a sequined dress being led by the hand into an unoccupied bedroom by a long-haired, underfed urchin who you thought was fast asleep on the couch. The key to this approach to flirtation is to pretend that you don't even see the woman you're sitting next to, but you touch her with the seeming unconscious familiarity of a sleeping child who puts his head on your lap as though it were the most natural thing in the world; its combination of innocence and audacity is breathtaking. It might not work for you and me, but it works for junkies in rock bands.

Similar to that is the Stanislavski method: "You are my sister." This is useful if you find yourself always talking to a woman as if she were a stranger. What I mean is the kind of easy confidence you would use if you were talking to your sister. The kind of confidence you have when you know a certain amount of affection and respect is taken for granted.

Never talk to a woman you are attracted to as if she were a stranger you need to impress. Talk to her as if you've loved her all her life. Pretend that you share a whole language and you don't need to translate, you don't need to explicate your subtle ironies. The idea is to cleanse your mind of all that boy-girl jittery falsity that comes when both of you know that you're really thinking about having sex. If you establish this air of mysterious and instant rapport, she may think to herself, my, it seems like I've known this man forever!

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Want more advice from Cary? Read yesterday's column.

By Cary Tennis

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