Guide to dating guys: NYC vs. Chicago



Having spent time in both Chicago and New York, I’ve noticed some serious differences in the dating pools: For one, I am able to wear heels in Chicago without fear of towering over the entire bar. Then again, there’s something to be said about a guy who will attend a Broadway show and not spend the entire intermission insisting on his straightness. In this game, there are no winners, just preferences. So are you dating in the right city? Let’s break it down.

His appearance

Chicago: Nothing like a navy blue Ralph Lauren polo and J. Crew chinos to adorn a 6-foot-4 frame topped with the backward Cubs hat he’s had since seventh grade. Everything—including his $9 haircut—is about utility. His favorite T-shirt is the one on top of the pile.

New York: With the amount you spend on rent, you can cut costs by sharing clothes with your boyfriend. He’s 5-7, appreciates distressed denim and has an enviable collection of James Perse V-necks. His favorite accessory is a $270 scarf. You will feel judged by how much better he looks than you.

Your weekends

Chicago: Start the weekend right by meeting at your boyfriend’s best friend from fifth grade’s house. (Matt always has a fridge full o’ cheap beer and a half-drunk bottle of Smirnoff for the ladies.) Saturdays are reserved for watching The Big Game at your man’s college bar, where you will ingest things with names like Cheesy Chili Tater Tot Explosion. On Sundays, your man will watch football and you will Drunk Brunch with your girls, one of whom just got engaged. This will happen every weekend until you are either married or spending half your paycheck on dating site subscriptions.

New York: On Friday nights, wait patiently for the “guy you’re talking to” (boyfriends do not exist in New York) to get off work at his investment bank. Start thinking about dinner at 11:30 p.m., then order in from Seamless. A few tick-tocks past midnight, exit your cab at a bar with no sign on the door that will not exist in four months. End the night with slice of pizza from Ray’s. Repeat Saturday. On Sundays, enjoy a $50-per-person brunch at a vegan quinoa-ery. Sit next to “that guy from Fun.” and Lena Dunham and expend all energy acting unimpressed.

His living situation

Chicago: Your boyfriend lives with two of his most loyal bros: Timmy from grade school and Chris from college. Without fail, one of the following—if not all—will be present as “décor”: that black and white poster of Michael Jordan with his arms spread out, a Cubs “W” flag or a stolen street sign.

New York: He lives with three roommates in a 400-square-foot apartment for the bargain price of $1,700 per person. Each month the roomies split the cost of a maid, a “necessity” for these boys. I mean, who else is going to clean up any bathroom residue from their Art of Shaving kits?

His willingness to commit

Chicago: Extremely high chance of commitment. Unwritten Midwestern law states that any two people in a monogamous relationship age 28 and up must marry. PERIOD.

New York: Zero to 1 percent chance of commitment, at least until age 53 or he starts taking Viagra, when he’ll start thinking about having kids.