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Valentine’s Day can be a complicated time of year, especially if your relationship can’t be defined in traditional terms. It’s 2020: who is even “in a relationship?” It’s not like you want to have anything in common with everyone in your high school graduating class, right?

V-Day is a holiday about packaging love. It’s about love and making everything at the drugstore more expensive by putting hearts on it, in the hopes that being inundated with pink and red will activate your insecurities about whether you’re doing your relationship (or lack thereof) correctly. It’s great to not give in, but also, listen, some of us are predisposed to FOMO. And what better way to loosely celebrate a Hallmark holiday than to go to a bar? You can go alone or with friends, you still get to have plans, but the plans are so low-maintenance that you could cancel last minute to watch TV in pajamas sans guilt. Here’s where to go based on your relationship status:

If you’re recently single (and in a crisis): Beauty Bar
Before you do something drastic (cut your own bangs, open a Kohl’s credit card, buy a hamster, etc.), dance out your stress at Beauty Bar. They’ve got a manicure and martini deal, a disco ball, and, as of press time, no rule against bringing a weighted blanket. 1444 W. Chicago, thebeautybar.com/home-chicago

If you’re recently single (and doing fine): Mariano’s bar
Breakups are hard, but you’re doing OK! You’re showering! Doing laundry! Talking to strangers’ dogs in a baby voice! And yeah, actually, it is fine to indulge in a glass of wine at the Mariano’s bar, just like your fellow Mariano’s bar comrades: two middle-aged women both named Donna who are gossiping about a tertiary Donna, and a brooding divorcee with a salt-and-pepper beard and a heavy gaze that says, “I have to pick up my daughter from soccer practice later,” eyes that, perhaps, really see you. You know what, maybe just get a bottle of wine to go. Find a location near you at marianos.com

If you’re “dating” someone in an open relationship: Cole’s Bar
Whether it’s the emotional compartmentalizing or the constant blurring of boundaries, the fun never ends when you’re hooking up with someone in an open relationship! Spend tonight at Cole’s, a good dive bar with a disproportionate number of magicians willing and ready to explain deepfakes to you. 2338 N. Milwaukee, colesbarchicago.com

click to enlarge RACHAL DUGGAN

  • Rachal Duggan

If you kissed your “platonic” friend two months ago and you are NOT talking about it: Berlin
Maybe see a drag show and then dance the night away without making eye contact? Platonically? 954 W. Belmont, berlinchicago.com

If you made “ironic” V-Day plans with someone from an app, but the only mutual interest you have is liking the South Park Facebook page in high school: Marz Brewing
In the words of my worst Tinder date, “I’m not much of a talker.” Marz Brewing has good food and a ton of experimental beer choices that you can pretend to know stuff about. If you run out of things to talk about, you can always default back to how cool their packaging art is. 3630 S. Iron, marz.beer

If you’re casually hooking up with someone and it’s super casual, you feel really casual because it’s very casual, nothing not-casual about this, haha, ha: Green Mill
Every time you hang out with your casual hookup, you’re never thinking, “What are we?” even if you guys are casually spending every weekend together making pancakes and casually playing an emotionally charged board game, casually. Why not go to a historic bar that does NOT remind you of your history with your casual hookup, with whom you could not imagine ever not being casual??? Haha! Ha. 4802 N. Broadway, greenmilljazz.com

If you’re sleeping with your ex: The Owl
Yes, I’m unfairly assuming it’s a bad idea, and, yes, I’m punishing you by telling you to go to a safe space for STDs to thrive without judgement. Going to the Owl could either get you two to resolve your issues in the name of survival OR stir a revelation that forces you to break up for real this time. 2521 N. Milwaukee, owlbarchicago.com

If you’re sleeping with your coworker: Three Dots and a Dash
No further questions here. This needs to be a stealth operation. Go to a dark bar with strong drinks in a part of town where you won’t run into your friends and prepare for scintillating conversation mainly focused on how annoying it is that Kevin from work taps on his desk too loud. 435 N. Clark, threedotschicago.com

click to enlarge RACHAL DUGGAN

  • rachal duggan

If you’re sitting in a mall food court doing one of those face mash-ups of what you and your high school crush’s baby would look like: Spyners Pub
Unfortunately, you’ve already been kicked out of Build-a-Bear Workshop for bringing vodka. But fear not! You can still commiserate at Spyners Pub. Some might say it’s the perfect dive: free popcorn, cheap drinks, karaoke, the sweetest bartenders, and a cozy and nurturing environment? What is this, the Montessori of dive bars? 4623 N. Western

If you’re dating someone too young to remember 9/11: Sluggers
You’re in your 30s and you’re dating someone who “understands” TikTok? You’re condemned to a terrible bar in Wrigley. Sorry! Rules are rules. 3540 N. Clark, sluggersbar.com   v

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