
Hey Chicagoland Singles!
(To see the entire list of events, PLEASE CLICK HERE)
Welcome back to another edition of Where’s Your Boo, where I tell you the following in exact verbatim:
‘Events with single people you must attend my Padawan’.
And like the great student you are, you ask: ‘Sensai, but which events shall I attend?’
And I say: ‘You have much to learn my Padawan. Read Where’s Your Boo’s weekly listing you must! And attend events in your age bracket you shall. And stop chasing emotionally unavailable gym influencers on Instagram at 1:12am, you also should.’
‘But Sensai, when and how will I know who is the one for me?’
‘You will know, because draw you closer together the force will….at the singles events, my Padawan….Not from hiding inside your apartment watching Netflix documentaries about serial killers.’
‘Thank you Sensai’
‘And your Netflix password give to me you must, my Padawan.’
The above is based on a true story, not inspired by any actual works of fiction….Coming to select theaters near you.
But until then, Happy Monday! And 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 18
Ivy Dating | Ivy Dating app: Bringing Dating Back to Real Life — May 18 • 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 | Speed Dating — May 18 @7:00 PM • Punch House, Chicago
The Office E.N.T | Coach Love Isn't Enough Presents Mix & Mingle @ ParkManor 75 Singles Only — May 18 @8:00 PM - 11:55 PM • Park Manor 75, Chicago, IL
Tuesday, May 19
Meet IRL | Meet IRL | Curated Speed Dating | Ages 32-42 ~Women's tickets sold out~ (Ages 32-42) — May 19 @6:30 PM • Wolf & Company, Chicago
ThrowbackDating | How to Date Over 50 - We’re Gonna Fix Your Picker (Ages 50+) — May 19 @7:00 PM • Google Meets, Chicago
Hot Potato Hearts | Workshop; A Love Storytelling Event — May 19 @7:00 PM • The Understudy, Chicago
Shuffle Dating | Speed Dating (Men & Women) (Ages 30-40) — May 19 @7:00 PM • Navigator Taproom, Chicago, IL
Wednesday, May 20
Meet Sweet | 30s–40s Singles Meet Up (Ages 30s–40s) — May 20 @6:00 PM – 9:00 PM • Eataly, Chicago
Birds of a Feather | Couples Speed Dating — May 20 @6:30 PM - 9:30 PM • Dearly Beloved, Chicago, IL
Thursday Dating | Wednesday | Dates for a Difference Singles Social | Carbon, West Loop — May 20 @7:00 PM • Carbon, Chicago
Chicago First Dates | Singles Ages, 40s & 50s - In-Person Speed Dating (Ages Women 44-56, Men 45-58) — May 20 @7:00 PM • Zia's Social, Chicago
Hot Potato Hearts | POC Speed Dating — May 20 @7:00 PM • Ludlow Liquors, Chicago
Table Talk | Singles Salsa Mixer — May 20 @7:00 PM - 10:00 PM • The River Kitchen & Bar, Chicago, IL
Thursday, May 21
ThrowbackDating | Throwback Dating x Tru Integrative Wellness (Ages 50+) — May 21 @4:30 PM • TRU Integrative Wellness, Fairview Avenue Downers Grove
Holy Nation Matchmaking | Memorial Day Virtual Christian Speed Dating (Ages 25-45) — May 21 @6:15 PM - 8:00 PM • Online, Online
Meet IRL | Meet IRL | ~Singles Only~ Thursday Night Social ✨ — May 21 @6:30 PM • The Dawson, Chicago
Jigsaw Dating | Singles Trivia Night 40-55, May 21st - Chicago (Ages 40-55) — May 21 @7:00 PM • Singles Trivia Night 40-55, May 21st - Chicago, Chicago
Chicago First Dates | Singles Ages 20s & 30s - In Person Speed Dating (Ages Women 24-38, Men 25-39) — May 21 @7:00 PM • Ivy Hotel - Streeterville, Chicago
Quirk Events | Board Game Speed Dating - Big Star Wrigleyville (Ages 20s & 30s) (Ages 20s-30s) — May 21 @7:00 PM - 9:00 PM • Big Star Wrigleyville, Chicago, IL
CitySwoon | Speed Dating Chicago | CitySwoon® | 33-45 years | at Machine Cocktail Bar (Ages 33-45) — May 21 @7:30 PM • Machine Cocktail Bar, Chicago
Thursday Dating | Thursday | Singles @ Shoreclub 🏖 | Shoreclub — May 21 @7:30 PM • Shore Club Chicago, Chicago
Friday, May 22
Coffee, Hip-Hop & Mental Health | Coffee Creates Chemistry: A Happy Hour for Singles — May 22 @5:30 PM - 7:30 PM • Coffee, Hip-Hop & Mental Health Cafe, Chicago, IL
Holy Nation Matchmaking | Virtual Christian Singles Mixer (Ages 40–55) — May 22 @6:15 PM – 8:00 PM • Online, Online
Chicago First Dates | Singles Ages 30s & 40s - In-Person Speed Dating (Ages Women 33-45, Men 35-48) — May 22 @7:00 PM • Coach's Bar & Grill, Chicago
Shuffle Dating | Speed Dating (Queer Women) (Ages 30-45) — May 22 @7:00 PM • The Albion Manor, Chicago, IL
Matchify | Singles Mingle Dinner Party Beatnik West Town — May 22 @7:30 PM - 9:00 PM • Beatnik West Town, Chicago, IL
Saturday, May 23
Meet Sweet | Singles Picnic at the Green City Market — May 23 @11:00 AM – 1:00 PM • 1817 N Clark St, Chicago
Hindu Vivah | Zoom Event | Single Parents (Ages All Ages) — May 23 @11:00 AM - 1:00 PM • Online, Online
MyCheekyGayDate | Gay Men Speed Dating @ Tabu - May 23rd 2026 (Ages 22–44) — May 23 @5:00 PM • Tabu, Chicago
Celina Atangana | Starlight Sapphic: Matchmaking @ Logan Arcade — May 23 @7:00 PM - 9:30 PM • Logan Arcade, Chicago, IL
MyCheekyDate | ✨Chicago Speed Dating | Saturday Night Ages 27-42 | Fancy a Go? (Ages 27–42) — May 23 @7:30 PM • Tabu, Chicago
Single N Minglin LLC | Spring Fling Speed Dating — May 23 @8:00 PM – 1:00 AM • 6947 S South Chicago Ave, Chicago
Sunday, May 24
Meet Sweet | Singles Picnic at the Wicker Park Farmers Market — May 24 @11:00 AM - 1:00 PM • 1425 N Damen Ave, Chicago, IL
MyCheekyDate | ✨ Chicago Speed Dating | Ages 36-48| Fancy a Go? (Ages 36–48) — May 24 @6:00 PM • Recess, Chicago
Shuffle Dating | Speed Dating (Men & Women) (Ages 30-45) — May 24 @6:00 PM • The Dandy Crown, Chicago, IL
Secret Supper Club Chicago | Red Flags Party | Singles Social Mixer — May 24 @7:00 PM - 9:00 PM • 3430 N Lincoln Ave, Chicago, IL
Know a single friend who’d love Where’s Your Boo? Forward this email to them, or send them this link to sign up!
And a Sneak Peek into a Few Events Coming Up in the following weeks:
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
Chaotic Singles Party | Chaotic Singles Salsa Night! — May 29 @8:00 PM - 11:00 PM • The Cubby Bear Chicago, Chicago, IL
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
(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!
And for more, subscribe to Where’s Your Boo?
