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Hey Chicagoland Singles!
(To see the entire list of events, click here)
Welcome to the 50th edition of Where's Your Boo! 🥂🥳
Allow me to reintroduce myself,
my name is Ashvin, oh, A to the S-H [vin]. I used to work IT in IL. Now I help people to meet I-R-L. 😎 🎵
Anyways, after 50 editions, I've learned a lot about Chicago's dating scene. But one thing has stood out from the very beginning: Chicagoland has a large, vibrant, and optimistic singles community, supported by incredible organizers who genuinely care about bringing people together.
If you're single and live in Chicagoland, you're in luck. There are dozens of singles events happening every week, from traditional speed dating to niche activity-based events, and the list keeps growing as more organizers continue to launch new experiences.
I'm also excited to share that Where's Your Boo is now creating content on Instagram! If you haven't checked it out yet, I'd love to have you there. And there's plenty more to come.
Finally, thank you for spending a few minutes with me each week. Attention is one of the most valuable things we have, and I don't take yours for granted. My goal is simple: every edition should help you discover something worth getting off the couch for.
Now, enough celebrating.
As always, we’re all here for one reason and one reason only.
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, July 20
Ivy Dating | Ivy Dating app: Bringing Dating Back to Real Life — July 20 • 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.
ThrowbackDating | Happy Hour on the Riverwalk (CHICAGO) (Ages 50+) — July 20 @5:00 PM • Riverwalk, Chicago
Hot Potato Hearts | 40+ Speed Dating (Ages 40+) — July 20 @7:00 PM • Solemn Oath Brewery Still Life, Chicago
Tuesday, July 21
Meet IRL | Meet IRL | 30+ Sapphic & Lesbian Speed Dating at Way Out (Ages 30+) — July 21 @6:30 PM • Way Out - Tuesday, July 21, 2026 at Way Out, Chicago
Hot Potato Hearts | Speed Dating — July 21 @7:00 PM • The Native, Chicago
Wednesday, July 22
Chicago First Dates | Singles w/ Advanced Degrees (Ages Women 33-45, Men 35-48) — July 22 @7:00 PM • Marriott Residence Inn - The Loop, Chicago
Shuffle Dating | Speed Dating (Queer Women) (Ages 27-43) — July 22 @7:00 PM • District Brew Yards, Chicago, IL
Skip the Small Talk | Millennial Speed-Dating (Monogamous) (Ages Millennials) — July 22 @7:00 PM - 9:00 PM • kibbitznest books, brews & blarney, Chicago, IL
Quirk Events | Board Game Speed Dating for Queer Women — July 22 @7:00 PM • Uptown Taproom, Chicago, IL
Fun Events | Chicago Singles Speed Dating Game Night — July 22 @7:00 PM • Barcocina Lakeview, Chicago, IL
Hot Potato Hearts | Bowling For Potato Soup — July 22 @7:30 PM • Avondale Bowl, Chicago
Thursday, July 23
(To see the remaining events this week, click here)
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 — July 29 @8:00 PM • River Shannon, Chicago, IL
Quirk Events | Board Game Speed Dating for Jewish Singles (Ages 20s-30s) — July 30 @7:00 PM - 9:00 PM • Uptown Taproom, Chicago, IL
Mohan Matchmaking | Mohan Matchmaking Chicago Mixer — August 2 @1:00 PM - 4:00 PM • LiqrBox, Chicago, IL
ThrowbackDating | Sounds of Summer: Hairbangers Ball at Cantigny (WEST) (Ages 50+) — August 8 @6:00 PM • Tank Park at Cantigny, Wheaton
Meet IRL | Meet IRL | Bookstore Speed Dating | Queer Women Ages 28+ (Ages 28+) — August 13 @6:30 PM • Passages Wine and Books, Chicago
(To see the entire list of events, click here)
What's the hardest part about dating right now?
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?