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I was a dork for all of high school and most of college, but also angry and sarcastic. Because of this, I didn’t date when I was supposed to, and I never learned how to flirt. I’m in my mid 20’s now, I’ve grown up and I have a great sense of self, but I have no idea what to say to cute girls to express genuine interest in talking to them. The generic, boilerplate advice that I always get for this is “You just need confidence.”
My problem is that growing up without confidence in myself has made it very difficult to distinguish being confident from being cheesy or arrogant. So I’ll ask, to a cute girl, what is the difference between a confident man and a corny jerk?
We’ve sort of talked about this topic on AAW before, but I think your specific quandary takes it in a different direction, so I’m happy to bring it up here. I don’t think meeting women or flirting is as simple as having confidence. It’s like telling someone to relax. JUST RELAX. Well now I definitely feel relaxed, thanks for that. Of course when you’re first learning to flirt you’re not going to feel confident. Confidence is built from experience and you don’t have any yet!
Guess what that means. You have to make yourself vulnerable. Yes. You’ll be nervous. You’ll say dumb stuff. You’ll get rejected. And just so you feel a little better? You’re talking to the queen of rejection–in many areas. At the end of college I thought to myself, fuck it, and gave myself permission to approach guys I was interested in instead of standing around trying to look available. Sometimes it worked out for me, sometimes not. The rejections sucked, but ultimately it was very liberating–the thing you’re afraid of happens and you live to flirt another day. Also, I’m a writer for a living. Rejection is the name of the game–soon I’m going to be able to wallpaper an entire house with all the rejection slips from literary journals and publishers who think my writing is horrible. Boo-hoo. Onward.
As far as confidence versus arrogance? I think I can make that clear if we define what exactly flirting is (and is not). Flirting is NOT pick-up lines. I mean, yes, sometimes flirting includes a pick-up line, but the best flirting, and the flirting that I’ve always preferred is not so structured and generic. What makes flirting great is when it’s personalized. “What’s your sign” is generic. You can say that to anyone, plus, it definitely comes off as cocky, cheesy, and usually obnoxious. Flirting does not require a comment about someone’s physical appearance. “Nice rack” will not make a woman feel special and coveted. It will make her feel like she needs some anti-bacterial soap. And flirting isn’t a solely verbal art. It includes smiling, appropriate touching, nodding, laughing. Finally, contrary to popular opinion and practice…flirting should be genuine. Don’t flirt with someone by telling them they have beautiful eyes when you don’t give a damn about their eyes.
So let’s put this all together. You’re at a party. You run into a lovely woman near the big shrimp (don’t the best parties always have really big shrimp?) and you comment on the great spread. She agrees. Game time. Ask her who she knows at the party. Let the conversation evolve from there. If there’s a natural breaking point, like her friend comes over to get her, or you run out of the things to say, don’t worry about it. Tell her it was nice to meet her, and let her go. Within the hour, find her again; you can walk right up to her without fear (or with less fear) because you’ve already met so you have an established connection. Comment on something she said earlier. Asking her questions is money. If you’re finding her engaging, let her know. “It’s so interesting that you XYZ….” This could be a comment on her job, her hobbies, her family, whatever. But again, say only what you mean. “It’s nice to meet someone randomly at one of these things that I can actually talk to.” Smile a lot, keep good eye contact. This is flirting. It’s not over the top, it’s not tinged with sexual innuendo. If you don’t get a number or it fizzles out, it’s NOT a wasted effort. You’re perfecting the art of intriguing women. It’s a prestigious line of work, with a long and glorious tradition.
Of course, it’s possible that I want everyone to put themselves out there and risk rejection so that I don’t feel like the lone loser in the universe. I guess that’s a chance you’ll have to be willing to take. Wink, smile, nod, appropriate touch.
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