These days, anyone with a generally apathetic attitude who dresses uniquely falls into the category of “hipster.” Over the years I’ve picked up my fair share of hipster women and I’ve found that no matter what kind of hipster sub-category they fall into, the same general pickup rules apply.
1. Be cool, but not that cool. There’s a pickup technique called “negging” that works brilliantly on hipster women. Compliment her, but follow it with something passive-aggressive. For example: “I really like your glasses. I saw similar frames on another girl on the way in.” Basically, you’ve said something nice, but now she’ll try to prove how much cooler she is than that other girl.
2. learn to dance. Better yet, enjoy it. I don’t think I’ve ever met a hipster who didn’t like to move. Whatever you do, don’t try to grind on a hipster girl.
3. Act like you (don’t) care. But only about cool stuff (stuff that she thinks is cool). All other shit is soooo beneath you. If she’s not dancing to the song the DJ is spinning, remark on how you’re so over that song. Chances are she’ll agree.
4. Wear what you want. Seriously, hipster fashion is so ridiculous that you could throw a dart in a thrift store, hit something and wear it out that night—it’d probably look cool and ironic. The more ridiculous you look, the more you’ll be looked upon as an innovator.
5. Don’t be touchy-feely. Most hipster women are fairly progressive when it comes to sex and the politics thereof. In fact, they’re downright feminists. So if you happen to score with one, don’t get all mushy and romantic afterward. Exchange numbers and pleasantries and then bounce like a 25-cent rubber ball.

San Diego Unseen: An Urban Portrait

