Jess, age 25
Neighborhood: River North
Jess works as an event planner, lives in a new condo, and always looks Instagram-worthy. She constantly finds herself on RSVP lists and work is perpetually interesting. She saw a cool band at Soho House last weekend. She’s gets VIP to music festivals for some reason. She doesn’t really like bottle service that much, but her friends get it all the time, so why not? Have you eaten at Momotaro yet? You haven’t? You have to try it.
Your first date: Per her suggestion, you meet her at the bar at Nellcôte. You’re attracted to her in a bird-sees-bright-plumage kind of way. You can’t really tell if she’s your type. She casually mentions her trust fund, twice. She disagrees with you a lot, but it seems exciting.
The inevitable breakup: You disagree, often. Spunky turns to abrasive. You get into a heated argument during dinner at a trendy restaurant and before the food arrives, ask for the check as discreetly as possible.