Hey Chicagoland Singles!
(To see the entire list of events, PLEASE CLICK HERE)
Hope you all had a great Mother’s Day weekend! And speaking of which, quick appreciation for the moms who spent years asking, “So…anyone special yet?”…Shoutout to the moms, aunties, grandmas, and mother figures holding entire family ecosystems together while the rest of us debate whether sending a second text after 48 hours is “too eager.” 😂
Still, every awkward first date, delayed text reply, and “should I go talk to them?” moment is really just people trying to find their future Boo. Future travel partner, future emergency contact, and future co-parent of tiny chaotic children who will one day ignore their texts too.
And where else to find this mysterious Boo? Right here in Chicagoland’s thriving singles and speed dating scene!
Summertime Chi is almost officially here and the singles events calendar is heating up fast.
Your favorite organizers all have events this week and beyond, and some are even hosting on the beach now (pinch me I’m dreaming).
So bye bye Après Ski, and hello 85 degrees.
Let’s jump into this week’s events!
Singles Events Happening This Week
Some events may not share certain criteria like age ranges. If you would like to be certain, please reach out to the organizers of the events you are interested in attending. Also, certain event titles below may state ‘SOLD OUT’. In some cases that is not true. Please ensure to visit the event listing site to confirm.
Monday, May 11
Ivy Dating | Ivy Dating app: Bringing Dating Back to Real Life — May 11 • An app that shows where singles are going out across Chicago each night. See which bars and clubs are active, where people are checked in, and choose your night based on where the energy is.
Hot Potato Hearts | Mask Required Speed Dating — May 11 @7:00 PM • Dandy Crown, Chicago
Tuesday, May 12
Meet IRL | Meet IRL | 30+ Queer Speed Dating at Way Out (Ages 30+) — May 12 @6:30 PM • Way Out - Tuesday, May 12, 2026 at Way Out, Chicago
Wednesday, May 13
Meet Sweet | 30s–40s Singles Meet Up (Ages 30s–40s) — May 13 @5:00 PM – 7:00 PM • Chicago French Market, Chicago
Birds of a Feather | ENM Speed Dating for Individuals — May 13 @6:30 PM - 9:30 PM • Machine Cocktail Bar, Chicago, IL
Hot Potato Hearts | Speed Dating — May 13 @7:00 PM • Easy Does It, Chicago
Quirk Events | Board Game Speed Dating (Queer Women) — May 13 @7:00 PM – 9:00 PM • Uptown Taproom, Chicago
ADDVentures | Single Awareness Dinner Monthly: Downers Grove | Foodies + New Friends — May 13 @7:00 PM • Restaurant of the Month, Downers Grove, IL
Shuffle Dating | Shuffle Dating Chicago (Ages 25–40) — May 13 @7:30 PM • District Brew Yards, Chicago
Thursday, May 14
Holy Nation Matchmaking | Virtual Christian Singles Mixer (Ages 24–40) — May 14 @6:15 PM – 8:00 PM • Online, Online
Meet IRL | Meet IRL | Curated Speed Dating | Gold Coast | Ages 28-34 (Ages 28-34) — May 14 @6:30 PM • Hopsmith Chicago, Chicago
Jigsaw Dating | Singles Arcade Night, May 14th (Ages 25-45+) — May 14 @7:00 PM • Dave and Busters, Rosemont, IL
Chicago First Dates | Singles Ages 30s & 40s - In-Person Speed Dating (Ages Women 33-45, Men 35-48) — May 14 @7:00 PM • Coach's Bar & Grill, Chicago
Pre-Dating Speed Dating and Lock & Key Events | Chicago Speed Dating (24–39) (Ages 24–39) — May 14 @7:00 PM – 9:00 PM • The Country Club Bar, Chicago
Butch McGuires | Singles Night Meet the Old Fashion Way (Every second Thursday of the month) — May 14 @7:00 PM • Butch McGuires, Chicago
Pitch Your Peeps | Queer Slide Deck Match Making — May 14 @7:00 PM • Nobody’s Darling, Chicago, IL
Thursday Dating | Thursday | Love, Lust or Stardust? Singles Mixer | River North — May 14 @7:30 PM • Stardust, Chicago
Shuffle Dating | Shuffle Dating Chicago (Ages 27–32) — May 14 @7:30 PM • The Albion Manor, Chicago
Friday, May 15
ThrowbackDating | Singles Play At Activate Games Chicago (Ages 50+) — May 15 @7:00 PM • Activate Games Chicago, East Ohio StreetChicago
Pre-Dating Speed Dating and Lock & Key Events | Chicago Speed Dating (30s–40s) (Ages 30s–40s) — May 15 @7:00 PM – 9:00 PM • The Country Club Bar, Chicago
Matchify | Singles Mingle Dinner Party — May 15 @7:00 PM – 9:00 PM • The Drake Oak Brook, Oak Brook
Saturday, May 16
Hindu Vivah | Zoom Event | Vegetarians/Vegans/Eggetarians (Ages Women 26-47, Men 28-48) — May 16 @11:00 AM - 1:00 PM • Online, Online
Jigsaw Dating | Coffee Shop Speed Dating 25-40, May 16th - Chicago (Ages 25-40) — May 16 @3:00 PM • Back of the Yards Coffeehouse, Chicago
The Tantra Institute | Tantra Speed Date Chicago — May 16 @5:30 PM – 8:30 PM • Moksha Yoga Center, Chicago
CitySwoon | Speed Dating Chicago | CitySwoon® | 40-55 years | at Bar Moxy (Ages 40-55) — May 16 @6:00 PM • Bar Moxy, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Brookfield, WI Bullwinkles — May 16 @6:30 PM • Bullwinkles at the Galleria, Brookfield
Break The Ice Social Events LLC | Singles Social Mixer St. Charles Arcada Speakeasy — May 16 @6:30 PM • Club Arcada Speakeasy & Restaurant, St. Charles
Chefrena | Flavors & Flirtation Singles Cooking Class — May 16 @6:30 PM - 9:30 PM • 8259 S Kedzie Ave, Chicago, IL
Jigsaw Dating | Sunset Speed Dating 25-40, May 16th - Chicago (Ages 25-40) — May 16 @7:00 PM • Sunset Speed Dating 25-40, May 16th - Chicago, Chicago
MyCheekyDate | ✨ Chicago Speed Dating | Saturday Night Ages 25-39 | Fancy a Go? (Ages 25–39) — May 16 @7:30 PM • Tabu, Chicago
Sunday, May 17
Meet Sweet | Sapphic Singles Brunch Meet Up — May 17 @10:00 AM – 12:00 PM • 2147 W Roscoe St, Chicago
Shuffle Dating | Speed Dating (Men & Women) (Ages 28-38) — May 17 @4:00 PM • The Dandy Crown, Chicago, IL
MyCheekyDate | ✨ Chicago Speed Dating | Ages 32-44 | Fancy a Go? (Ages 32–44) — May 17 @5:00 PM • Tabu, Chicago
Break The Ice Social Events LLC | Singles Social Mixer Wheeling, IL Cooper's Hawk — May 17 @6:00 PM • Cooper’s Hawk Winery & Restaurant, Wheeling
Dorothy | IRL: Singles Mixer at Dorothy — May 17 @6:00 PM - 11:00 PM • Dorothy, Chicago, IL
ThrowbackDating | Throwback Daters Lounge (Ages 50+) — May 17 @7:00 PM • Google Meets, Chicago
Secret Supper Club Chicago | Red Flags Party | Singles Social Mixer — May 17 @7:00 PM - 9:00 PM • 3430 N Lincoln Ave, Chicago, IL
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And a Sneak Peek into a Few Events Coming Up in the following weeks:
Single N Minglin LLC | Spring Fling Speed Dating — May 23 @8:00 PM – 1:00 AM • 6947 S South Chicago Ave, Chicago
River Shannon | Singles Night — May 27 @8:00 PM • River Shannon, Chicago
Rooftop Cinema Club | Singles Night (‘There’s Something About Mary’ Screening) (Ages 25–35) — May 28 @6:30 PM • Rooftop Cinema Club Fulton Market, Chicago
ThrowbackDating | Singles in Service: Beach Clean-Up(Ages 50+) — May 30 @9:00 AM • Gillson Beach, Michigan Avenue Wilmette
Thursday Dating | Saturday | Puppy Love @ PB&J | West Loop — May 30 @1:00 PM • PB&J: Pizza Beer and Jukebox, Chicago
West Town Social Club | Thirsty Thursday Singles Night (Cougars & Cubs) (Ages men ages 25–39 / women ages 35+) — June 4 @7:00 PM – 9:30 PM • The Low Horse, Chicago
HinduVivah | In-Person Speed Dating for US/Canada Raised Hindu Singles (Ages 26-47) — June 13 @1:00 PM - 5:00 PM • India HUB, Schaumburg, IL
The Rooted Space | Salsa Speed Dating (Ages 30-45) — June 20 @7:30 PM • The Rooted Space, Chicago, IL
(To see the entire list of events, PLEASE CLICK HERE)
That’s it for this week.
And as always, thank you for reading another edition of Where’s Your Boo?. Your boo is waiting for you. So get out there, and let us know how it goes!
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