Win a date with a lady arm wrestler at My Bloody CLLAW-entine on Sat 2/13. Credit: James Rand

Sure, Valentine’s Day often means drowning in candy hearts and teddy bears, but not all celebrations of love need to be so saccharine. This year the city has some more savory romantic offerings like a boozy brunch, lady arm wrestlers, and embarrassing entries from teenage diaries. 

There’s a full list of Valentine’s Day happenings here; below are 11 events for you to enjoy without getting a cavity:

Champagne, Chocolate, and Comedy Treat yourself this Valentine’s Day with generous samples of champagne courtesy of Veuve Clicquot and Moët & Chandon, paired with three chocolates created by Blackbird restaurant. Following the tasting is a performance of The Explorers Club, a comedy set during the declining days of the British empire. Sun 2/14, 2 PM, Windy City Playhouse, 3014 W. Irving Park, 312-374-3196,, $40.

Cupid Has a Heart On . . . In Bed This long-running musical sketch comedy portrays a host of relatable romantic situations through feisty songs and risque numbers. All audience members will receive a glass of champagne and a Valentine’s Day goodie bag. Sat 2/13, 8 and 10:30 PM, Stage 773, 1225 W. Belmont, 773-327-5252,, prices vary.

Heart and Soul Valentine’s Day Brunch Kick off Valentine’s Day with a boozy brunch date at Logan Square’s Parts and Labor. The bar will be offering a full brunch menu and $5 “bleeding heart” pom-mosas, and there’s a live DJ set from the Windy City Soul Club. Sun 2/14, Parts and Labor, 2700 N. Milwaukee, 773-360-7840,

Last Kiss Uptown Underground regulars Pervesk’ Burlesk’ present a Valentine’s twist on their dark, twisted neo-burlesque show. Sat 2/13, midnight, Uptown Underground, 4707 N. Broadway, 773-867-1946,, $20.

My Bloody CLLAW-entine Let the Chicago League of Lady Arm Wrestlers woo you this Valentine’s Day at this 24th annual benefit match, featuring live music, the baddest arm-wrestling ladies in Chicago, and a raffle for the chance to win a date with one of them. Sat 2/13, 9:30 PM, Logan Square Auditorium, 2539 N. Kedzie, 773-252-6179 or 866-468-3401,, $10.

Naked Girls Reading This special Valentine’s Day installment of the salacious reading series focuses on the theme “absinthe and the French erotica,” featuring exclusive absinthe samples from Chicago Distilling Company. Fri 2/12, 8 PM, Studio L’amour, 4001 N. Ravenswood, suite 205, 312-243-6690,, $20.

Strip Joker Nothing goes together quite like comedy and nudity, which makes this new comedy series the perfect Valentine’s Day activity. Each headlining act must take the Strip Joker challenge: every time a joke flops (or rocks) an article of clothing must be removed. Thu 2/11, 8 PM, Gorilla Tango Theatre, 1919 N. Milwaukee, 773-598-4549,, $15.

Valentine Shmalentine Mortified presents Valentine Shmalentine, which features everyday people reading the most pathetic and embarrassing passages from their teenage diaries. A portion of the proceeds will benefit the Night Ministry, a Chicago-based housing organization. Sat 2/13, 6:30 PM, Mayne Stage, 1328 W. Morse, 773-381-4554,, $25.

Valentine’s Day Karaoke Fundraiser Sing your heart out this Valentine’s Day to help raise funds for the independent literary event Chicago Zine Fest. Enjoy drink specials, manicures, and a 50/50 raffle. The event is 21+. Sun 2/14, 8 PM, Beauty Bar, 1444 W. Chicago, 312-226-8828,, $5.

Valentine’s Dinner at Lula Cafe Lula Cafe is offering a prix fixe four-course special Valentine’s Day dinner. The regular menu will also be available. Sun 2/14, Lula Cafe, 2537 N. Kedzie, 773-489-9554,, $65.

Will You Accept This Rose? Get your Bachelor fix this Valentine’s Day as one of Under the Gun’s improv teams replicates an episode of the Bachelor with inspiration from the audience’s own love lives. Featuring special guest Ed Swiderski, a Bachelorette winner. Sun 2/14, 6 PM, Under the Gun Theater, 956 W. Newport, 773-270-3440,, $12.