Meet her at the bar 15 minutes late, and make sure to emphasize three times in your explanation how busy you are right now, because things are slammed at work. Let that be a prelude to the three and a half hours you’re going to spend talking mostly about your work. Take off your jacket, and roll up the sleeves on your gingham button-down, because it’s pretty hot in this bar and you’re not afraid of looking a little casual.
Order something whiskey-based, or beer, and ask her what she wants – suggest the most typically feminine cocktail you see on the menu, and only be impressed with her order if she also orders something whiskey-based, or beer. If she does, make sure to comment on the fact that she can “drink like a man,” or “doesn’t like chick drinks,” alluding to how gross those fruity cocktails are. Secretly think that those cocktails look pretty damn delicious.
(They are pretty damn delicious.)
Make sure she’s ready to be seated, and offer to get her another drink before you move to the table (making it her third one before the menus even hit the table). When she declines, order another one anyway, because you like to get a good buzz going when you’re on a first date – it takes the edge off. Take a quick look at the menu and then set it down, and tell the waiter you need some time in the driest, most uninterested way you possibly can. Watch her meekly order a glass of water as he’s walking away.
Tell her about what you do, making an effort to explain the nuances of your industry and how exactly your job works. Tell her it’s not a big deal that she doesn’t know a lot about finance – most people don’t. Explain to her your average day, and outline why exactly it’s so busy right now. Every time you mention the busyness, follow it up with a little aside about how you love your work, and wouldn’t do anything else, even if it didn’t pay so well. Briefly wonder if it’s weird to allude to how much you make, but go ahead and give her a very narrow range of salaries to indicate yours. Get a little thrill from knowing that she knows how well you’re doing for a 28-year-old.
Ask her a few perfunctory questions about her line of work. Assume, based on its liberal-arts nature and the fact that she lives in a neighborhood you’ve never been to, that she doesn’t make that much. Steer the conversation back to the menu.
Make fun of a few of the more difficult-to-pronounce menu items on the upscale, non-Western menu. Say it a few times until you think you finally got it right, then ask her to try her hand – congratulate her on what seems like a def pronunciation. Remark that “girls are always better with foreign languages.” Mention the time you went to Thailand for a friend’s bachelor party, and all of the crazy shit you did there. Tell her you really don’t like spicy food, and reiterate that to the water. Confirm twice that the thing you ordered is, indeed, not served spicy. Order another drink.
Over your chicken-based dish, make a vaguely sexist joke. If she laughs along, immediately like her more. If she seems apathetic, start backpedaling to pass the joke off as ironic. If she makes a serious comment about sexist jokes reinforcing damaging real-life dynamics, fight her back on that because you’re just drunk enough to do so. Argue that real sexism doesn’t exist anymore, citing several of your female coworkers (who are, themselves, outnumbered 1:15 by men).
Insist on getting the check, but make a comment about how this place must be trendy because it’s very expensive. Let her reach for her wallet twice, but turn her down each time. Tell her she looks pretty, and start getting more complimentary as you walk closer to the door. When you’re outside, ask if she wants to take a cab with you. When she insists that she’s taking the metro, tell her that it’s your treat. As she declines, heading towards the nearest metro entrance, grab her arm to pull her in for a goodnight kiss. When she dodges it and kisses your cheek, immediately lose interest in that evening.
Text her three times over the next four days just in case, and when she doesn’t respond, call her a bitch.