Hey Chicagoland Singles!
To those of you who are new here, allow me to reintroduce myself. I’m Ashvin, and this is ‘Where’s Your Boo?’, Chicagoland’s weekly guide to singles and dating events. My job? To remind you that love won’t appear through endless swipes. It happens when you actually go out, to the dozens of singles events that I list each week happening all over Chicagoland.
And what a time to join us... because drum roll, please….Halloween week is finally here!
This week is special for two reasons:
It’s the only time of year where “Boo” has three meanings: ghost 👻 , your future soulmate ❤ , and thumbs down 👎 (hopefully not all in one night).
It’s also the one week when you can get more eyeballs than a Victoria’s Secret model….as long as you wear a costume.
Chicagoland’s loaded with parties where you can show off (or scare off) in full costume glory. OnLoveXperiences’ Halloween Bash and MeetIRL’s Halloween Singles Party are some of the big ones in the singles and dating events scene (details below). They’re the perfect places to say “Boo” to your potential boo. Just maybe don’t boo their costume if you’re hoping for a second date.
If you’re still stressing over what to wear, last week’s issue had 10 great last-minute costume ideas. But in the spirit of last-minute, I’m throwing in a few more this week for the true procrastinators (keep reading).
So get ready for an epic week! There are 20+ events packed into this issue, which means no excuses for staying in. And no matter what you wear, where you end up, or who you meet, just remember this: have fun, be responsible, and stay spooky!
Happy Halloween! 🎃
Singles Events Happening This Week
Tuesday, October 28
Throwback Dating | Throwback Daters Fall Dinner & Wine Pairing (Ages 48–65) — October 28 @ 7:00 PM • Pixca Seasonal American Bistro, Highland Park (IL)
MeetIRL | Curated Speed Dating at Midwest Coast (Ages 28-36) — October 28 @ 6:30 PM • Midwest Coast Brewing Company, West Town (Chicago)
Wednesday, October 29
OnLoveXperiences | Halloween Bash (Ages 35ish to 50) – Oct 29 @5:30pm – Chicago Chop House (River North)
Shuffle Dating | Speed Dating @ District Brew Yards (Ages 32–42) — Oct 29 @7:00 PM • District Brew Yards, Chicago
Cityswoon | Matched Speed Dating in West Loop – Carnivale | (Ages 32-44) — October 29 @ 7:30 PM • Carnivale, West Loop (Chicago)
Thursday Events | 35+ Speakeasy Singles Mixer | Clandestino, River North (Ages 35+) — October 29 @ 7:30 PM • Clandestino Cocktail Social Club, River North (Chicago)
Thursday, October 30
Chicago First Dates | Single Professionals, 40s & 50s – In-Person Speed Dating (Women 43–55, Men 45–58) — October 30 @ 7:00–9:00 PM • Moretti’s Ristorante & Pizzeria, Edison Park (Chicago, IL)
Chicago First Dates | Singles Ages 30s & 40s – In-Person Speed Dating (Women 33–45, Men 35–47) — October 30 @ 7:00–9:00 PM • Ivy Hotel Bar & Lounge, Streeterville (Chicago, IL)
MeetIRL | Meet IRL Singles Only Halloween Party (Show us your best costumes!) (Ages 21+) — October 30 @ 6:30 pm • Hoste, Chicago
Thursday Events | Love at First Swing (Ages 21+) — October 30 @ 7:30 PM • Five Iron Golf, River North (Chicago)
Friday, October 31 (Halloween)
MeetIRL | Singles Pickleball Night: Halloween Edition (Ages 21+) — October 31 @ 6:15 PM • SPF Pickleball, Chicago
Saturday, November 1
MyCheekyDate | Saturday Night Speed Dating @ Tabu – Ages 25-39 — November 1 @ 7:30 PM • Tabu, Chicago
Sunday, November 2
Chicago First Dates | Single Professionals, 20s & 30s – Westmont, IL (Women 23–35, Men 25–38) — November 2 @ 5:00–7:00 PM • Neat Kitchen & Bar, Westmont (IL)
Break The Ice Social Events LLC | Singles Social Mixer – Gurnee Cooper’s Hawk — November 2 @ 6:00 PM • Cooper’s Hawk Winery & Restaurant, Gurnee (IL)
MyCheekyDate | Speed Dating @ Tabu (Ages 36–48) — Nov 2 @6:00 PM • Tabu, Chicago
Events Next Week:
meet irl | Curated Speed Dating (Ages 30–39) — Nov 4 @6:30 PM • Solemn Oath Brewery Still Life, Chicago
Shuffle Dating | Shuffle Dating Chicago – District Brew Yards (Ages 30–40) — November 5 @ 7:00 PM • District Brew Yards, West Loop (Chicago)
CitySwoon | Midweek Speed Dating @ Bar Moxy (Ages 35–49) — Nov 5 @7:30 PM • Bar Moxy – River North, Chicago
meet irl | Curated Speed Dating @ Hopsmith (Ages 22–32) — Nov 6 @6:30 PM • Hopsmith, Chicago
Intelligent Singles Network | Intelligent Singles Mixer in Chicago — Nov 6 @7:00 PM • Tre Denari, Chicago
Shuffle Dating | Speed Dating @ The Albion Manor (Ages 35–45) — Nov 6 @7:00 PM • The Albion Manor, Chicago
Chicago First Dates | Singles Ages 20s & 30s – In-Person Speed Dating (Women 24–38, Men 25–39) — November 6 @ 7:00–9:00 PM • Ivy Hotel Bar & Lounge, Streeterville (Chicago, IL)
meet irl | Singles Basketball Social — Nov 7 @6:30 PM • Wintrust Arena, Chicago
Flirty Friday at Anthem Ale House | Flirty Friday – Naperville Singles Mixer — November 7 @ 8:00 PM • Anthem Ale House, Naperville (IL)
Jigsaw Dating | Chicago Singles Event: Speed Dating (Ages 25-45) at Coffee Shop (Ages 25-45) — November 8 @ 3:00–5:00 PM • Coffee shop venue TBD, Chicago
Jigsaw® Dating | Singles Happy Hour – November 8 (Ages 25–45) — Nov 8 @ 7:00 PM • Joy District, 112 W Hubbard St., Chicago
Break The Ice Social Events LLC | Singles Social Mixer – McHenry DC Cobbs — November 8 @ 6:30 PM • DC Cobbs, McHenry (IL)
Break The Ice Social Events | Singles Social Mixer @ Egg Harbor Café — Nov 9 @11:00 AM • Egg Harbor Café, Orland Park (IL)
Shuffle Dating | Shuffle Dating Chicago – The Dandy Crown (Ages 27–34) — November 9 @ 4:00 PM • The Dandy Crown, River West (Chicago)
Break The Ice Social Events | Singles Social Mixer @ Cooper’s Hawk — Nov 9 @6:00 PM • Cooper’s Hawk Winery & Restaurant, South Barrington
Tip of the Week
This week’s Tip: More last-minute costume ideas.
This week’s tip is for those who live life on the edge. For those who call procrastination a typical Tuesday. And for those who wait until the very last second to pick a Halloween costume. Because waiting 24 hours before just wasn’t enough to kickstart their adrenaline rush.
Last minute ideas:
“Quarterback”: Tape a quarter to your back.
Tourist in Your Own City: Fanny pack, bad hat, camera. Ask locals where the Bean is.
Plot Twist: Normal outfit, then carry a piece of paper that says, “Turns out, I was the villain all along.”
Freudian Slip: Write random Freudian terms (“ego,” “id,” “Oedipus”) on slips of paper and tape them to your clothes.
Smart Cookie: Tape cookies to your shirt and wear glasses.
Gaslighter: Carry a small lantern, tell people they’re imagining things.
Girl Math Professor: Blazer, messy bun, calculator, and a whiteboard that says “If I pay with cash, it’s free.”
The Gym Bro: Cut-off tank, shaker bottle, constant flexing.
The Bear: White tee, blue apron, and always mutter “Yes, Chef.”
Blockbuster Employee: Blue polo, “Be Kind Rewind” sticker
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:
Chicago First Dates | Singles Speed Dating @ Moretti’s Ristorante & Pizzeria (Women 24–38, Men 25–39) — Nov 13 @7:00 PM • Moretti’s Ristorante & Pizzeria – Edison Park, Chicago
Break The Ice Social Events | Singles Social Mixer @ Spartan Ale House — Nov 14 @6:30 PM • Spartan Ale House, Naperville
meet irl x Boppn | The Great Singles Scavenger Hunt! — Nov 15 @3:00 PM • The Dawson, Chicago
Jigsaw® Dating | Coffee Shop Speed Dating 40+ @ The Avondale Coffee Club (Ages 40+) — Nov 15 @3:00 PM • The Avondale Coffee Club, Chicago
Tantra Speed Date | Tantra Speed Date® – Chicago (Meet Singles Speed Dating) — November 15 @ 5:30 PM • Moksha Yoga Center, Wicker Park
Chicago First Dates | Singles Speed Dating @ Moretti’s Ristorante & Pizzeria (Women 33–45, Men 35–47) — Nov 20 @7:00 PM • Moretti’s Ristorante & Pizzeria – Edison Park, Chicago
The Feels | The Feels Chicago, edition 5: a mindful singles event— November 24 @ 6:30–9:30 PM • Chicago
CitySwoon | Thanksgiving Eve Speed Dating @ City Winery (Ages 29–49) — Nov 26 @7:30 PM • City Winery – West Loop, Chicago
Throwback Dating | Singles In Service: Holiday Gift Wrapping with Kids Above All (Ages 40+) — Dec 7 @1:00 PM • Kids Above All’s Better Life Distribution Center, Des Plaines
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?
