I almost never have engaged in trying to pick up total strangers (way too shy) but today decided to give it a whirl on an impulse. Getting out of the subway, a lady unlocked her bike from a parking meter, and I said to her, “Excuse me, do you just leave your bike locked up here all day long and no one tries to steal it?”
To my mild surprise, we got into a conversation that included bike-stealing, her recent relocation to a neighborhood further away that she needed to bike to, because she lost her job, so I found out her where she worked, which is a restaurant I’ve eaten in, so we talked about that a little bit, and we exchanged names, and I gave her my card which has my cel phone and email on it, and it was amazingly easy and comfortable to do, talking to a strange and attractive stranger.
Yet it sucked. Immediately afterwards, I reviewed all the things I’d done wrong. I offerred to help her find work in her chosen field (biology) where I don’t really know anyone and now if she calls me it may be because she thinks I’m going to be useful professionally, which I’m really not, and I had chances to compliment her which I ignored (like when she said she doesn’t have any friends here–instead of saying how hard it was to believe that a pretty, charming woman wouldn’t have more friends than she knew what to do with, I just went’ “Umm, yeah, having friends is good for job-searching…” like a total doofus) and mainly what I failed at was communicating that I was attracted to her–I probably could have asked if she’d like to have a cup of coffee with me, or stressed (in a non-creepy way) how much I hope she’d call me very soon or anything that would signal my interest in her.
Seems to me the hard part isn’t really striking up a conversation with a strange woman but it’s having the type of conversation that will lead to something. That’s the part of picking up that always seems difficult to me. It always seems to me that there’s some kind of risk, but there isn’t really–she was a total stranger to me, and if she thought I was creepy or unattractive or if she was married or gay or anything that would be a non-starter, she was perfectly free to say so, or to tell me to fuck off, and I’d have lost nothing. But it always feels so risk-intense for some reason that I rarely do this, and when I do I always think of much better ways I could have behaved.
" In other words, a baloney compliment like that might well backfire, but more likely than that is that she’d be thinking “Oy vey, what a dork! Does he really think I’d fall for a stupid line like that?”
