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Hey Chicagoland Singles!
Welcome back to another edition of ‘Where’s Your Boo?’ (post-Marathon edition), your guide to all the singles and dating events happening in and around Chicago. Whether you live in West Loop or Schaumburg, we have an event for you!
Chicago just wrapped another record-breaking marathon, with more than 50,000 runners hitting the streets! And we have to pay homage the right way.
Every mile is a grind, a test of both the body and mind. Each one finished is its own victory. Which is why we have 26 events lined up for you in this edition! (Yes, the Halloween Costume Party is waiting at the finish line.) And as always, I’m sharing new conversation starters, post-marathon edition (keep reading).
Attending one dating event is also a victory on it’s own. Nobody asked you to lace up, show up, or make small talk at a 5-mile-per-hour pace withot spilling your drink. And nobody told you to leave with a new contact that just might be your new PR (personal romance).
That is all you. Your friends, family and I are just the ones on the sidelines cheering you on. You are the one crossing the finish line, with the digits of your future boo in hand.
Singles Events Happening This Week
Tuesday, October 14
Break The Ice Social Events | Singles Social Mixer – Oak Brook Wonderverse — October 14 @ 6:30 PM • Wonderverse, Oak Brook (IL)
Wednesday, October 15
Shuffle Dating | Shuffle Dating Chicago Events (Ages 33-45) — October 15 @ 6:30 PM • The Parlour at Park & Oak (Glen Ellyn, IL)
Thursday Events | Singles Speakeasy Mixer | Clandestino, River North (Ages 21+) — October 15 @ 7:30–9:30 PM • Clandestino Cocktail Social Club, River North (Chicago)
Cityswoon | Speed Dating Chicago | In-Person | Ages 30-42 — October 15 @ 7:30 PM • Tre Denari, Chicago
Thursday, October 16
Shuffle Dating | Speed Dating (Ages 32-42) (Ages 32–42) — October 16 @ 7:00 PM • Albion Manor, Chicago
Chicago First Dates | Singles Ages 20s & 30s – In Person Speed Dating (Women 24–38, Men 25–39) — October 16 @ 7:00–9:00 PM • Ivy Hotel Bar & Lounge, Chicago
Cityswoon | Speed Dating Chicago | In-Person | River North (Ages 44-54) — October 16 @ 7:30 PM • Moxy Bar, River North (Chicago)
Friday, October 17
MeetIRL | Friday Night Singles Social (Ages 20s & Early 30s)— October 17 @ 6:30 PM • Verve Wine, Chicago
Break The Ice Social Events | Singles Social Mixer – Lombard Miller’s Ale House — October 17 @ 6:30 PM • Miller’s Ale House, Lombard (IL)
Saturday, October 18
Jigsaw Dating | Chicago Singles Event: Speed Dating (Ages 40+) at Coffee Shop (Ages 40+) — October 18 @ 3:00–5:00 PM • The Avondale Coffee Club, Chicago
Break The Ice Social Events | Singles Social Mixer – St. Charles Alley 64 — October 18 @ 6:30 PM • Alley 64 Bar & Grill, St. Charles (IL)
Jigsaw Dating | Chicago Singles Event: Happy Hour Mixer (Ages 40+) — October 18 @ 7:00–9:00 PM • Never Have I Ever, West Loop (Chicago)
Sunday, October 19
Break The Ice Social Events | Singles Social Mixer – Kildeer Cooper’s Hawk — October 19 @ 6:30 PM • Cooper’s Hawk Winery & Restaurant, Kildeer (IL)
Chicago First Dates | Single Professionals, 30s & 40s – Schaumburg, IL (Women 33-45, Men 35-47) — October 19 @ 5:00–7:00 PM • Finn McCool’s Irish Sports Pub, Schaumburg (IL)
Events Next Week:
Chicago First Dates | Singles Ages 30s & 40s – In-Person Speed Dating (Women 33-46, Men 35-48) — October 23 @ 7:00–9:00 PM • Moretti’s Ristorante & Pizzeria, Edison Park (Chicago, IL)
MeetIRL | Curated Speed Dating at Half Acre Beer Co. (Ages 24-34) (Ages 24-34) — October 23 @ 6:15 PM • Half Acre Beer Co., Ravenswood (Chicago)
Cityswoon | Matched Speed Dating in River North (Ages 27-39) — October 23 @ 7:30 PM • Kitchen Kocktails, River North (Chicago)
Throwback Dating | Singles Night at Activate Games Naperville (Ages 45-60) — October 24 @ 7:00 PM • Activate Games, Naperville (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)
Jigsaw Dating | Chicago Singles Event: Happy Hour Halloweekend (Ages 25–45) (Ages 25–45) — October 25 @ 7:00–9:00 PM • Joy District, River North
Shuffle Dating | Shuffle Dating Chicago – Queer Women Edition (Ages 28–40, Queer Women Only) — October 26 @ 4:00 PM • The Dandy Crown, River West
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Tip of the Week:
This week’s Tip: Conversation Starters, post-marathon edition
Whether you are the one approaching or being approached at a singles event, I’ve shared five converstation starters below in the spirit of this year’s Chicago Marathon!
(WARNING: usage may lead to blank stares, sighs, and the potential loss of brownie points. Please proceed with caution.)
So, did you run the marathon…or were you more of a professional spectator like me?
What would your motivational sign say if you were cheering people on?
What song would be on your dating playlist at mile 10, when you’re tired but not giving up?
If you could design the after-party for a marathon, what would it look like?
What’s harder: finding parking in Chicago, or running 26 miles? (my personal favorite 😆 ).
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:
Throwback Dating | Throwback Daters Fall Dinner & Wine Pairing (Ages 48–65) — October 28 @ 7:00 PM • Pixca Seasonal American Bistro, Highland Park (IL)
OnLoveXperiences | Halloween Bash (Ages 35ish to 50) – Oct 29 @5:30pm – Chicago Chop House (River North)
Thursday Events | 35+ Speakeasy Singles Mixer | Clandestino, River North (Ages 35+) — October 29 @ 7:30 PM Clandestino Cocktail Social Club, River North (Chicago)
MeetIRL | Meet IRL Singles Only Halloween Party (Show us your best costumes!) (Ages 21+) — October 30 @ 6:30 pm • Hoste, Chicago
MeetIRL | Singles Pickleball Night: Halloween Edition (Ages 21+) — October 31 @ 6:15 PM • SPF Pickleball, Chicago
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!
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?