Dating is a wonderful way to meet new people and possibly find someone to split rent with you. But sometimes you date someone for a couple of months, then wake up one morning and realize that life would be better if you were dating someone else. Or dating no one. It’s probably time to break up with this person (in the nicest way possible, of course).
We’ll be honest - you should probably host this breakup in your home. But maybe you lost your keys or don’t own enough chairs, and if that’s the case, try a bar. You’ll need one that isn’t weirdly quiet or full of people who might recognize you. Pick one of these spots, then start brainstorming how to tell someone that you don’t want to have to text them anymore.
This restaurant’s name will set the tone, foreshadowing what’s about to happen. Lonesome Rose is a casual all-day Tex-Mex spot in Logan Square with a light and bright front bar area and very good drinks. While you’re here, go ahead and order the nachos, which you can concentrate on eating while your significant other stammers “wait...what?” over and over again. If it seems like the conversation is going to take a while, but you want a change of scenery, check out Golden Teardrops. It’s the basement bar downstairs that also has a strangely appropriate name.
If you would like to do this breakup at someone’s home (just not your own), consider heading to Happy Village, which is like visiting an old house. This Ukrainian Village bar has a ping-pong space inside and a backyard that feels like you’re hanging out at your aunt’s place in the suburbs, except you can leave whenever you want. Which will probably be soon.
Even though it’s new, Good Measure in River North has the atmosphere of a dive bar, with red neon lights and a big wooden bar that looks like it belongs in Classic Chicago Bar Magazine. And since it’s also one of Chicago’s Darkest Restaurants you can easily hide your expressionless face and/or their tears. The cocktail list is well-rounded and affordable, with drinks priced around $12. Text them to meet you here after work when you want a low-key spot to end something.
This spot on the border of Chicago and Evanston is a great, not-too-well-known option if you don’t want to risk seeing anyone you might want to date in the future. Inside it’s dark and small, with reclaimed church pews for seats. The cocktail menu is straightforward, focusing on excellent renditions of the classics, like Old Fashioneds.
If you need to do this breakup right after work, rip the band-aid off at Beatnik On The River in the Loop. This place is owned by the same people as Beatnik in West Town and has the same over-the-top atmosphere. The cafe inside has a giant antique marble bar, and there’s a patio full of ornate furniture overlooking the river. If the conversation gets too uncomfortable you can always escape by jumping onto a passing architectural tour boat.
Kuma’s has very good burgers, but for your purposes, it’s more important to know that the restaurant plays loud, angry heavy metal. You don’t have to like this kind of music, but if your significant other needs to process their rage, it helps to have Slayer blasting the entire time. Hopefully.
You can’t go wrong with The Delta in Wicker Park. It’s a casual, laid-back place with good cocktails and an upbeat atmosphere. Everyone who works here is very friendly, and that coupled with great food and drinks means you leave here in a better mood than when you arrived. That might not be the case while you’re explaining that you’ve met someone else, but at least the short menu of small plates won’t leave you trapped in a full dinner once the conversation begins.
Two things can always help bad news go down easier: gin and warm chocolate chip cookies. Plenty of both are readily available at Scofflaw in Logan Square, a spot that’s dimly lit and cozy without being romantic, with a large fireplace that can hopefully lull your significant other into a relaxed, meditative state. The drink menu focuses on quality gin cocktails, and the aforementioned fresh-baked cookies also happen to be free. Unlike those non-refundable Second City tickets.
While you don’t want the breakup spot to be too quiet, you don’t want it to be so loud that you have to shout the fact that you won’t be attending their sister’s wedding after all. The Press Room is a basement wine bar on an out-of-the-way corner in the West Loop, and it keeps a low-key ambience even when it’s crowded. It’s an easy place to hang all night, in case you were planning on walking around the block and going right back in once the coast is clear.
You guys never took that trip to France that you halfheartedly talked about (one time), and it definitely isn’t happening now. While going to Cafe Marie-Jeanne in Humboldt Park might rub salt in this painful wound, the casual atmosphere and long wine list make it an ideal spot to have an uncomfortable conversation. Also, the rustic French food is really, really good - so if things go awry at least you have the duck frites.
Meet them out front, point at the sign, and explain that you, too, are a lone wolf, which is why this is just never going to work out. That might be hard for them to accept at first, but the affordable drinks and tasty snacks inside will make it easier. Plus, it’s right next door to Au Cheval, so if anyone needs to eat their feelings, that’s a very good place to start.
“I’m not ready for a relationship right now” is what you say to someone who is perfectly nice, but ultimately boring. That’s exactly the case with The Smith, a restaurant in River North with a giant bar and just fine food and drinks. In fact, if you ask someone to meet you here with little to no explanation, they’ll know what’s going to happen.