Neighborhood: River North Jess works as an event planner, lives in a new condo, and always looks Instagram-worthy. She doesn’t really like bottle service that much, but her friends get it all the time, so why not? She’s been at her company for 18 months and is thinking about jumping ship to another startup. Your first date: Jo meets you for a cocktail at Japonais right after she finishes up work at 8pm.

She constantly finds herself on RSVP lists and work is perpetually interesting. The perks are better there, they have these cool chairs and there’s a barista on site. You’re super impressed by her smarts, she talks about work a lot, but you think her glasses are hot.

Her pops works in construction and her brother owns an auto garage where her cousins hang out all day, even though it never actually looks like anyone is fixing anything.

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Neighborhood: Humboldt Park Kelly doesn’t listen to The Men anymore.

They used to be cool, but now they sound like Wilco.

After dinner, you suggest beers at a nearby dive but she takes you to an upscale lounge instead.

The inevitable breakup: You’re sick of her referring to chefs you don’t know by name, and break things off NOT at dinner.

She’s listening to a band you’ve never heard of right now. Your first date: You drink too many cheap beers and whiskey shots at Longman & Eagle, and make out after sharing a cigarette outside.

She saw them at a basement show in a DIY venue last weekend. She used to hang out at East Room, but the bartenders there are assholes. She has to go home though, because it’s late and she actually works at a law firm full-time. Neighborhood: Andersonville Allison is a project manager at an ad agency and loves telling people that she gets free lunches at work even though she brings her own lunch because she’s a strict vegan.

A friend introduces you, and after seeing her at the bar several more times, you finally get up the courage to ask her out.

Your first date: You go see a local band at Quenchers and share a tater-tot pizza.

Your first date: You meet at a Cuban joint and eat oxtail stew.

She asks you about your favorite restaurants and you struggle to keep up with the conversation.

Work is important after all, it keeps her eye on retirement. Surprisingly, she likes her booze and you finish up the night drinking bourbon at Motel Bar.