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I’m a 20-something New Yorker, and living in New York I find myself constantly surrounded by the kind of women you want to elope to Santorini with. On the train, in coffee shops and in bars, I can’t count the number of times I’ve seen a woman and been instantly stricken. I’ll often work up the courage to start walking over to say hi, but I always stop when I realize I have no idea what I would say.
Pop culture has taught me that the man-who-is-more-confident-than-me always knows something appropriate to say in a situation like that. In your opinion, is there any way to approach a strange woman on the street or on the subway without coming off as weird or overly-forward?
Here is the secret to hitting on women: be genuine. No lines, no ego, just yourself: “Hi, I noticed you across the bar/street, and I just wanted to come over and introduce myself. I’m Nate. May I buy you a drink/walk with you for a bit?” The reason this strategy works is that it allows you to keep your dignity whether or not the woman is interested in you. If the woman is interested, you’ve just set yourself up as a polite, honest human being–not a bad way to start a love connection. If the woman is not interested, it allows her to gently turn you down–“That’s very sweet of you, but I have a boyfriend/I’m really late for an appointment.”–and both of you get out of it alive.
It’s very, very hard to politely respond to a man who says: “Baby, you must be a broom, ’cause you swept me off my feet!” A woman who is not interested will react with a horrified face, or some choice words telling you where you can go. Sorry guys, maybe it’s an overreaction, but our creep-meter immediately goes up and all we want to do when we hear such a terrible line is create as much distance between ourselves and you. (And yes, fine, perhaps it’s possible to stumble across a woman who thinks lines are hilarious and charming, but if you do, she’s one of five such tolerant women in the whole country, so take that luck and buy a lottery ticket while you’re at it.)
The hard truth of the matter is that to meet and connect with someone, you have to make yourself vulnerable. I know it’s difficult to walk up to a beautiful stranger and subject yourself to possible rejection. But, I’ll spare you some surprise right now: you WILL be rejected from time to time. It’s a guarantee. When it happens, be gracious and exit the stage: “Okay, take care.” Then try again with someone with whom you’d like to elope to Mykonos.
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