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?
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
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