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Neal O'Bryan

24 reasons it sucks to be single in Chicago

Written by
Time Out editors
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For the most part, being single in Chicago is pretty amazing. The city is packed with 20- and 30-somethings, great bars to meet other singles and so many things to do you won’t even have time to wish you had a boyfriend or girlfriend. But sometimes, well, being single just sucks. You’re allowed to have a little pity party for yourself—we won’t tell anyone. Here are 24 reasons being single in Chicago isn’t all it’s hyped up to be.

1. You’ve got no one to nurse a hangover with after a night at 4am bars. Or worse…

2. You have to deal with ushering a stranger out of your apartment after a night at 4am bars. Woof.

3. You don’t have anyone to split Fat Rice’s signature dish with—or one of Lost Lake’s shareable punches.

4. When you feel super nasty after four days of Lollapalooza, no one’s obligated to tell you you’re attractive. You just gotta sit in your own filth. Tell me I’m pretty, damn it!

5. There's no chance of making it on the Kiss Cam at Bulls or Hawks games. Unless Benny the Bull is feeling extra frisky.

6. Running into people you’ve hooked up with. C’mon, Chicago isn’t that big.

7. There’s no one to split Ubers with after a long night out.

8. No one’s there to tell you, “Uh, no, you really shouldn’t get that Blackhawks tattoo…”

9. The most reliable person in your life is Tamale Guy.

10. Matching with someone cute on Tinder, then finding out they live in Rogers Park—just a casual 90-minute CTA ride from your Ukrainian Village apartment, nbd.

11. Your couple friends start moving out to neighborhoods where they can actually afford houses. Which means…see you never!

12. Accidentally stumbling into one of the most romantic places in Chicago. Ugh, they’re everywhere.

13. You can’t justify getting a dog—between work and commuting, it’s a two-person job. (Cats, on the other hand, are a different story.)

14. That means hanging out at dog-friendly patios is pretty lonely. 

15. Your couple friends start doing couple-y things like going to museums and parks instead of hanging out with you and day-drinking.

16. You have to convince your friends to splurge on the best restaurants in Chicago for a not-so-romantic dinner with you.

17. It’s either an entire deep-dish pizza or no deep-dish pizza. There’s nowhere in the middle for single Chicagoans.

18. You can’t picnic on the Lakefront by yourself—you’d just look like a creep lingering around some family barbecue.

19. All those couples holding hands on the Lakefront trail when you’re just trying to jog—or worse, those couples biking side-by-side.

20. Ordering in for one. Delivery fees are no joke in this city!

21. Cooking for one—farmers markets, we love you, but good produce ain’t cheap in Chicago.

22. Living with a roommate. Everyone has their horror stories.

23. Visiting your couple friends’ apartments and salivating at what a double-income can afford in this city.

24. So. Many. Dudes. In. Cubs. Gear. On. Tinder.

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