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If you’re tired of being asked, “So, what are you doing for Valentine’s Day?”—or feeling vaguely pressured to get boo’ed up for the weekend—this holiday can start to feel like… a lot. For anyone not in a relationship (or simply not in the mood for forced romance), the long weekend of love can be more daunting than delightful. But fear not: Chicago has you covered.
From tongue-in-cheek concerts poking fun at lovebirds to singles mixers and comedy shows built on bad-date material, the city is offering plenty of ways to opt out of the hearts-and-roses agenda. Here are eight events that provide a welcome respite from the onslaught of bouquets, prix-fixe menus and candy hearts.
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Anti-Love Trivia
Sleeping Village, 3734 W Belmont Ave
Feb 15 at 7pm
This unhinged trivia night is devoted to breakups, bad dates and the cultural history of romantic misfires. Come with friends, come alone or come with the one person who always insists they “don’t care about Valentine’s Day” but clearly does. It’s free to play, and winning feels especially triumphant when the night’s theme is failure.
Interactive screening of The Princess Bride
Music Box Theatre, 3733 N Southport Ave
Feb 14 at 11am and 9:15pm
The Music Box invites you to watch The Princess Bride the way it was meant to be seen: loudly quoted and surrounded by fellow romantics and skeptics alike. Prop bags included, dignity optional. It’s sword fights, true love and jokes you’ve been waiting years to scream in unison with a room full of strangers.
Crying At The Shed
Salt Shed, 1357 N Elston Ave
Feb 12–14
If you’re in the mood to feel your feelings in public, Crying at the Shed is a three-night film fest devoted to love in all its awkward, yearning, and occasionally unhinged forms. Expect movies about romance, loneliness and the strange places we go looking for connection—plus a few immersive touches that make the whole thing feel like stepping into someone else’s memory. Opening night includes a live set from Lael Neale, in case you’d like your heartbreak with a soundtrack.
Bowling Singles Mixer at Timber Lanes
Timber Lanes Bowling Alley, 1851 W Irving Park Road
Feb 14 at 8pm
Meet other singles the old-fashioned way: under fluorescent lights, wearing smelly rented shoes and hyping up strangers throwing bowling balls. The night includes unlimited bowling and a drink, which is helpful whether you’re flirting, striking out or doing both at once.
Mortified Chicago’s Doomed Valentine Show
Lincoln Hall, 2424 N Lincoln Ave
Feb 14 at 8pm
Mortified invites brave souls to exhume their most cringeworthy teenage crushes and first kiss disasters for public consumption. It’s part group therapy, part confessional booth and fully committed to reminding you that no one peaked emotionally at 14. You will laugh, and you may also feel seen in ways you didn’t request.
Name A Cockroach Unveiling
Brookfield Zoo, 8400 31st St, Brookfield, IL
Feb 14 at 10am
For those who prefer their Valentine’s Day with a little catharsis, Brookfield Zoo will once again unveil the names of cockroaches dedicated to exes, enemies and every situationship in between. Your donation gets you a certificate and the quiet satisfaction of knowing your romantic nemesis now shares a name with a hissing insect.
F*ck Love: Anti-Valentine’s Drag Brunch
Simone’s Bar, 960 W. 18th St., Pilsen
1–3 p.m. Feb. 15
This drag brunch leans into the deliciously messy side of Valentine’s weekend. Expect big performances, strong drinks and an audience that knows love is best served with a side of sarcasm. Hang after the show for photo ops and tasty drinks.
Self-Love Movement: An Open Introduction to Dance
Bim Bom Studios, 5226 W Belmont Ave
Feb 15 at 1pm
This gentle, come-as-you-are dance workshop is less about perfect form and more about figuring out how your body actually wants to move. You’ll be guided through low pressure exercises and end with a short group flow that feels more like collective exhaling than choreography. No experience required—awkwardness welcome.