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Hey Chicagoland Singles!
Walking into a singles event can feel like the scariest part.
But here’s the secret: everyone else is just as nervous!
Confidence isn’t about being fearless, it’s about taking action anyway. Whether it’s saying ‘Hi’ to the person next to you in line for a drink or asking someone if they’ve been to the venue before, small moves break the ice faster than you think.
This week, I’ve even included simple, actionable steps on handling approach anxiety (don’t worry, I did the hard work and consulted ChatGPT so you don’t have to). Scroll down to check it out, then put them into practice at the events below.
Singles Events Happening This Week
And now, for this week’s events. We’ve got shuffleboard. We’ve got game nights. And of course, we’ve got good old-fashioned….(drum roll please)…..speed dating. You won’t want to miss these
Thursday, Sep 11
Meet IRL | Curated Speed Dating (Ages 30-39) – Sep 11 @6:30pm • The Dawson, Chicago
Chicago First Dates Singles Speed Dating (Ages 30s & 40s) — Sep 11 @ 7 pm • WineStyles, Norwood Park
Thursday | Singles Shuffleboard Night | Royal Palms — Sep 11 @ 7 pm • Royal Palms Shuffleboard Club, Wicker Park
Friday, Sep 12
Throwback Daters Night at Activate Games Naperville (Ages 45–60) — Sep 12 @ 7 pm • Activate Games, Naperville
CitySwoon TGIF Matched Speed Dating in West Loop (Ages 43–55) — Sep 12 @ 7:30 pm • Carnivale, West Loop
Saturday, Sep 13
Tantra Speed Date — Sep 13 @ 5:30 pm • Moksha Yoga Center, Chicago
Jigsaw Dating Singles Happy Hour (Ages 25–45+) — Sep 13, 7–9 pm • Port and Park Bistro, Chicago
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And a Sneak Peak into a Few Events Coming Up in the following weeks:
Party of 7 Chicago Singles Game Night – A Twist on Speed Dating (Ages 20s and 30s) — Sep 17 @ 7 pm • Barcocina Lakeview
Throwback Dating | Skyline Singles Soiree (50+) – Sep 18 @6:30pm • Avli on the Park, Chicago
Shuffle Dating Speed Dating Event (Ages 30–40) — Sep 17 @ 6:30 pm • The Parlour at Park & Oak, Glen Ellyn
Thursday | Mystery Matchmaking | Parlay, Lincoln Park — Sep 18 @ 7:30 pm • Parlay, Lincoln Park
Relish Speed Dating (Ages 24–36) — Sep 25 @ 7 pm • Untitled Supper Club, Chicago
“Once you just get curious about people and places, you lose all that anxiety about approaching people. You lose that ridiculous idea that every interaction has two possible outcomes: approval or rejection.”
― Matthew Hussey, Get the Guy: Learn Secrets of the Male Mind to Find the Man You Want and the Love You Deserve
Here are 3 steps ChatGPT (or Cha-Cha affectionately) advises on how to handle approach anxiety at dating events:
#1 Before entering an event: Ask yourself, “What do I want to learn about this place or the people here today?” (“Is SPIN Chicago as loud as the photos make it look?”)
#2 When you meet someone: Be curious. “What brought you to this event—the thrill, the challenge, the chance to meet someone beyond swipe culture?”
#3 Drop the “approve-or-reject” mindset. Focus on collecting stories, not dating metrics: “That was fun—what’s next?”
Thanks Cha-Cha 😃
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?
If you would like to share your experiences from singles and dating events you’ve attended, would love to hear it!
Also, full event calendar launching on our website soon. Stay tuned!