In partnership with
Hey Chicagoland Singles!
This week, think of dating events like test drives. Speed dating, mixers, and activity-based nights (pickleball, trivia, karaoke, etc.) each have their own rhythm. One gives you structure, another lets you float around, and the third gives you something fun to focus on while you meet people.
Go in with an open mind. Try one of each style and notice where you feel most at ease. Once you find the format that fits you best, lean into it. That’s where you’ll meet the right people and actually enjoy the process. Keep reading below for some quick tips and tricks to help you succeed in each type of event.
Now, let’s see what’s happening around Chicagoland this week!
Singles Events Happening This Week
Wednesday, September 24
- Shuffle Dating | Shuffle Dating Chicago Events (Ages 29-37) — September 24 @ 7:00 PM • District Brew Yards, Chicago
- River Shannon | Singles Night— September 24 @ 8:00 PM • River Shannon, Lincoln Park (Chicago)
Thursday, September 25
- Throwback Dating | Throwback Daters Night Out: Cubs vs. Mets at Wrigley Field (Ages 50-65) — September 25 @ 5:30-9:30 PM • Wrigley Field
- Thursday Events | One Last Rooftop Rendezvous | West Loop (Ages 21+) — September 25 @ 7:30-9:30 PM • Tetto Chicago, West Loop (Chicago)
- Relish Speed Dating (Ages 24–36) — Sep 25 @ 7 pm • Untitled Supper Club, Chicago
- Chicago First Dates | Singles Ages 20s & 30s — In-Person Speed Dating (Women 23–35, Men 23–38) — September 25 @ 7:00 PM • WineStyles Norwood Park
Friday, September 26
- MeetIRL | Friday Night Pickleball: Singles Night at SPF (Ages 21+) — September 26 @ 6:15 PM • SPF Pickleball, Chicago
- Chicago Seriously Searching Singles | Singles Social Mixer (Ages 21+) – Sep 26 @5:30pm – Oak Park Conservatory Rubenstein Garden
Saturday, September 27
- Cityswoon | Speed Dating Chicago | In-Person | Ages 30-45 (Ages 30-45) — September 27 @ 6:00 PM • Depot 226, West Loop (Chicago) Eventbrite
- Jigsaw Dating | Chicago Singles Event: Happy Hour Mixer (Ages 25-45) (Ages 25-45) — September 27 @ 7PM • Never Have I Ever, River North (Chicago)
- Northwest Side Chicago Board Game Friends | Singles Game Night Mixer - September 27 @ 7:00 PM • Stay and Play Game Cafe, Irving Park (Chicago)
Sunday, September 28
- Thursday Events | Sunday | Sunday FUNDAY Kickoff | Over/Under, Lincoln Park (Ages 21+) — September 28 @ 11:30 AM-3:30 PM • Over/Under Sports Bar, Lincoln Park (Chicago)
- Shuffle Dating | Shuffle Dating Chicago Events (Ages 25-32) — September 28 @ 4:00 PM • The Dandy Crown, Chicago
- SpeedChicago Dating | Singles Events (Ages 29-42) (Ages 29-42) — September 28 @ 6:00 PM • Recess, Chicago
Looking for unbiased, fact-based news? Join 1440 today.
Join over 4 million Americans who start their day with 1440 – your daily digest for unbiased, fact-centric news. From politics to sports, we cover it all by analyzing over 100 sources. Our concise, 5-minute read lands in your inbox each morning at no cost. Experience news without the noise; let 1440 help you make up your own mind. Sign up now and invite your friends and family to be part of the informed.
And now…..as promised.
Tips & Tricks for Each Event Style:
Speed Dating
Have a go-to opener. A light question like “What’s the most fun thing you’ve done this month?” helps you skip small talk and stand out.
Take notes between rounds. Jot down a quick word or two so you remember who was who when it’s time to choose matches.
Mixers
Don’t camp out. Move around the room every 10–15 minutes so you meet more people and avoid blending into the wallpaper.
Use the buddy system. If you come with a friend, split up during conversations. Doubling up can intimidate new people.
Event-Based Nights (Pickleball, Trivia, Karaoke, etc.)
Lean into the activity. Focus on having fun with the activity, game or sport, and let conversation flow naturally from the shared experience.
Be encouraging. Whether it’s cheering a trivia guess or laughing off a missed shot, positivity makes you more approachable.
Know a single friend who’d love Where’s Your Boo? Forward this email to them, or send them this link to sign up!
A Few Events Coming Up Next Week:
· MeetIRL | Curated Speed Dating (Ages 28-38) — September 30 @ 6:30 PM • Midwest Coast Brewing Company, West Town (Chicago)
· Throwback Dating | Live Jazz on the Cliff: An Evening with Throwback Daters (Age 50+) (Ages 50-70) — October 3 @ 5:30-10:00 PM • The Cliff Dwellers, Chicago
· West Town Social Club | Thirsty Thursday Singles Night (Ages 35+) – Oct 9 @7pm – The Low Horse
· Single Professionals, 30s & 40s ‒ Westmont, IL (via Chicago First Dates) — October 19 @ 5:00-7:00 PM • Neat Kitchen & Bar, Westmont (IL)
· Tantra Speed Date | Tantra Speed Date® - Chicago! (Meet Singles Speed Dating) (Ages 18+) — October 25 @ 5:30-8:30 PM • Moksha Yoga Center, Armitage & Wicker Park (Chicago)
· OnLoveXperiences | Halloween Bash (Ages 35ish to 50) – Oct 29 @5:30pm – Chicago Chop House (River North)
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!