Unless you’re an ego monster or a stalker, nobody likes picking up strangers. It forces you to make yourself vulnerable. You feel corny. Hesitant. Plus, what if she’s insane? The cost-benefit analysis is hazy.
But you can’t swear off the pickup entirely. You’ll be bopping along, happy with the couch you just bought, liking your job, going to the gym, maybe even taking multivitamins, and then—boom—you’ll see a girl, reading that book, with her hair, and those shoes, and she’ll laugh and you’ll feel joy and it’s awesome and you’ll want it. What are you going to do? Talk to her or never see her again? You should talk to her.
Chris Rock is right: “A woman knows if she’s gonna fuck you within the first five minutes of meeting you.” So here’s how you should open: Glance at her face, her torso region, her shoes, and then back at her face while smiling a medium-size smile. Keep it natural. Looking a girl up and down should take no longer than counting to four. Don’t eye-roger the crap out of her and then lick your lips like a zoot-suit-wearing-wolf cartoon. If she doesn’t flee like you’ve got a rattail or a $30,000 ostrich attaché, her curiosity is piqued and you’re in the running. Trust.
Let’s say the lovely girl is at a bar and half-turned toward you—and she stays that way. Reassure her by looking a little sheepish when you’re in her sight line. Your countenance should be all “I know, right? What even is this?” Let her know that you don’t think she’s a sure thing. (Even if she is wearing an abbreviated dress and enthusiastic underwear.) From there, say hi. (Just like that: “Hi.”) Tell her your first name; offer to buy her a drink. Depending on how convincingly you imply that you’re baffled by happenstance (because neither of you does this, ever)—and contingent upon just how enthusiastic her underwear is—close. How? Well, the two of you aren’t going to rut on a barstool, so an extraction is required. Say the following: “Would you be horrified if I suggested we go someplace quieter?”
Here’s another scenario: the pavement pickup. This one’s a numbers game, so you can’t take squat personally, because women have zero vetting mechanisms in place. It’s all about delineating yourself from the street crazies. Remember: You are strangers. You could have eight jars of formaldehyde-pickled human face in your weekender. The next thing out of your mouth could be about her juicy pussy or Jesus. (It happens.) So bravely say hi, like earlier. Don’t say: I love your Chloë Sevigny for Opening Ceremony spring 2012 cutout shirtwaist. The sidewalk is no place for getting fancy! If she’s not dead-eyed, forge on. Say: “My name’s [name]. I know this is nuts, but could I buy you a cup of coffee or a drink nearby?”
In any setting, momentum is key. If you can lock time with her, do. If the situation is harried, like on mass transit, try to get her contact or give her yours and promise that if it’s a no-go, you’ll shove off as far away as that guy (and then point to a guy a half car away). Assure her that you won’t make it weird. Make no mention of “Missed Connections.”
Oh, a couple of quick notes about exchanging contact info: Don’t hand a girl your card. If you use Facebook as a verb, you’ve already lost. If she does give you her phone number, do the unthinkable and call. Everyone hates phones, but not texting is a good curveball.
If the call goes to voice mail, this is your time to shine. Be adorable. Clear your throat. Do that thing where you say a running commentary of exactly what you’re doing: “This is me calling you on your phone, leaving you a voice mail, hoping you’ll call back, because then I can take you out.” That’s the best! If she calls you back, chances are she’s fucking you. Just don’t screw this up for her, okay?
