Hey Chicagoland Singles!

Hope you had a restful Thanksgiving and enjoyed all the food, family, friends, Stranger Things, 6–12 inches of snow, and those deeply questionable pies. Now that the November holiday haze is officially over, it’s time to trade leftovers for real-life connections. December is here, and with it comes one of the busiest months of the year for singles events.

Yes, Chicagoland’s snow season ❄ has arrived and the couch is calling your name. Yes, you’re probably starting to pack for your winter escape to Hawaii where beaches 🏖 and flip-flops whisper sweet nothings. And yes, Elf is somehow getting its ninety-ninth rewatch. But I’m telling you, this month’s lineup of singles events might just help you meet your future Boo sooner than you think.

December’s lineup has something for every kind of mood and personality. From cozy singles dinners and high-energy pickleball to trivia nights, volunteering and community service, speed dating, happy hours, ugly sweater Christmas parties, and even sauna + cold plunge events, December is packed with ways to find your Boo without relying on another swipe.

We’re also sharing a growing list of community-based events for those who want to connect within their own circles, including Christian, Muslim, LGBTQ+, and other affinity-based gatherings. Whether you’re looking for romance, friendship, or just a stronger sense of community, there’s plenty to explore.

All in, there are over 50 singles events happening this month alone. So, if you’ve been waiting for the perfect time to get back out there and find your boo, December just made the decision for you (rhyme intended 🤓).

Now let’s get onto the upcoming 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.

Tuesday, December 2

Wednesday, December 3

Thursday, December 4

Friday, December 5

Saturday, December 6

Sunday, December 7

Next Week’s Events:

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:

Where’s Your Boo is also partnered with Variants.

Looking for a word game experience with a modern twist? Well, look no further! Variants sharpens your mind just like other popular word games, but the challenge is different. Guess the five words with a special constraint!

Click here to play!

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?

Keep Reading

No posts found

© 2026 Where's Your Boo?.

Report abuse

Privacy policy

Terms of use

Powered by beehiiv