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Hey Chicagoland Singles!
This week’s edition arrives a few days late, but with double the value: events for this weekend plus a look at next week. And, this week’s tip: 4 Halloween-themed conversation starters!
And yes, Halloween is creeping closer. A costume party singles event is already on this month’s calendar. Time to start hoarding toilet paper for your mummy costume!
(Me in college. Confidence: 10/10. Execution: 2/10)
Singles Events Happening This Week
Friday, Oct 3
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
Saturday, Oct 4
CitySwoon | Speed Dating | Chicago | Singles Event 7211 (Ages 35–49) — October 4 @ 6:00 PM • Bar Moxy, River North, Chicago
MyCheekyDate | MEN SOLD OUT**| Chicago Speed Dating | Speed Chicago (Ages 25–39) — October 4 @ 7:30 pm • Tabu, Chicago
Sunday, Oct 5
Shuffle Dating | Shuffle Dating Chicago Events (Ages 29-37) — October 5 @ 4:00 PM • The Dandy Crown, Chicago
MyCheekyDate | Chicago Speed Dating (Ages 36–48) — October 5 @ 6:00 pm • Tabu, Chicago
Next week:
Tuesday, Oct 7
Meet IRL | Curated Speed Dating | Women’s tickets sold out! (Ages 35-49) -Oct 7 @6:30pm - Solemn Oath's Still Life, Chicago
Wednesday, Oct 8
CitySwoon | Speed Dating | Chicago | Singles Event 7212 (Ages 33–45) — October 8 @ 7:30 PM • Carnivale, West Loop, Chicago
Thursday, Oct 9
Shuffle Dating | Speed Dating (Ages 32-42) (Ages 32–42) — October 9 @ 7:00 PM • Albion Manor, Chicago
West Town Social Club | Thirsty Thursday Singles Night (Ages 35+) – Oct 9 @7pm – The Low Horse
Friday, Oct 10
Jigsaw Dating | Chicago Singles Event: Ping Pong Social (Ages 25–45) (Ages 25–45) — October 10 @ 6:00 PM • SPIN, Chicago
Thursday Events | Singles After Dark at Bandit (Ages 21+) — October 10 @ 7:30PM • Bandit, West Loop (Chicago)
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Tip of the Week:
This week’s tip: Small Talk Edge
When starting conversations, skip the boring prompts. Try something new, maybe even Halloween Themed!
Option 1: Costume Nostalgia
“Skip the usual ‘what do you do?’ and ask: What’s the most ridiculous costume you’ve ever worn?
Option 2: Candy Debate
“Instead of small talk about the weather, try: What Halloween candy would you trade away first?
Option 3: Scary Movies
“Swap out the boring ‘where are you from?’ for: What’s your go-to scary movie, or the one you refuse to watch?
Option 4: Fall Traditions
“Ditch the resume questions. Ask: Apple cider or pumpkin spice?
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And a Sneak Peek into a Few Events Coming Up in the following weeks:
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+ • Moksha Yoga Center, Armitage & Wicker Park (Chicago)
OnLoveXperiences | Halloween Bash (Ages 35ish to 50) – Oct 29 @5:30pm – Chicago Chop House (River North)
MeetIRL | Meet IRL Singles Only Halloween Party (Show us your best costumes!) (Ages 21+) — October 30 @ 6:30 pm • Hoste, Chicago
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!
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