WINDSOR SINGLES, Stand up comedy and matchmaking

Schedule

Fri Oct 16 2026 at 07:00 pm to 09:00 pm

UTC-04:00
Location

138 University Ave W | Windsor, ON

Advertisement
“Laugh. Mingle. Maybe Match.”
About this Event

Looking to laugh and maybe meet someone new? WINDSOR Singles is a one-of-a-kind night that blends stand-up comedy with real-life matchmaking. Kick back with a drink, enjoy a lineup of hilarious comedians, and take part in a fun, low-pressure dating experience designed to spark genuine connections.

Whether you’re single and ready to mingle or just in it for the laughs, expect a night full of good vibes, unexpected moments, and plenty of opportunities to connect.

Come for the comedy… stay for the chemistry.


Event Photos

Advertisement

Where is it happening?

138 University Ave W, 138 University Avenue West, Windsor, Canada

Event Location & Nearby Stays:

Tickets

CAD 6.85 to CAD 22.90

Know what’s Happening Next — before everyone else does.
Hassan Chaudhry
Host or PublisherHassan Chaudhry

Tags

Comedy in Windsor

Ask AI if this event suits you

Keep exploring

Discover more events in Windsor

More concerts, festivals, nightlife and things to do happening near you.

Fri, 16 Oct at 05:00 pm Chalk Pastel Country Landscape Class for Adults and Teens

3919 Howard Avenue,Windsor,N9G 1N9,CA

WORKSHOPS ART
Fri, 16 Oct at 06:00 pm Windsor Make & Mingle Friday, October 16th, 6pm-9pm

839 Ottawa St., Windsor, ON, Canada

ART
Fri, 16 Oct at 06:30 pm Blue Roses: Watercolor Technique with Crayola Washable Markers

Expressive Brush Art Studio

FITNESS ART
Fri, 16 Oct at 08:00 pm Friday Comedy Session LIVE At Tipsy Toucan (Oct 16th)

The Tipsy Toucan

FITNESS COMEDY
Sat, 17 Oct at 09:30 am Lee Valley Tools Windsor Store - Turn an Acrylic Pen

3009 Howard Ave

FITNESS
Sat, 17 Oct at 11:00 am Windsor-Essex Winter-Ready Home Show 2026

THE WFCU CENTRE

Sat, 17 Oct at 01:00 pm Walking in the Forest – Kids Pencil Drawing Class

Expressive Brush Art Studio

ART WORKSHOPS
Sat, 17 Oct at 07:00 pm 3rd Annual R.Y.O.T. For Charity Pre-Halloween Bash🎃

Meteor

NONPROFIT CHARITIES
Fri, 27 Feb at 08:00 pm Next Stop Comedy at The Lion's Head Tavern! - Windsor, ON

Lion's Head Tavern

COMEDY ENTERTAINMENT
Thu, 07 May at 07:00 pm Open Mic Storytelling - Tales of the Town (May)

Circuit

OPEN-MIC STORYTELLING
Fri, 08 May at 07:30 pm ACT Presents: Six: Teen Edition

Capitol Theatre Windsor

ENTERTAINMENT MUSIC
Fri, 08 May at 08:00 pm Sail Away With Remedy

The Man's Shop & Barbershop Bar

TRIPS-ADVENTURES ENTERTAINMENT
Sat, 09 May at 08:00 pm The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (May 9th)

The Tipsy Toucan

COMEDY FESTIVALS
Thu, 14 May Mo Amer

The Colosseum At Caesars Windsor

Fri, 15 May at 08:00 pm The Colosseum At Caesars Windsor Presents Mo Amer

The Colosseum at Caesars Windsor

Fri, 15 May at 08:00 pm Mo Amer Ticket + Hotel Deals

The Colosseum at Caesars Windsor

Fri, 15 May at 08:00 pm Mo Amer at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor

CALENDAR
Fri, 15 May at 08:00 pm Standup Comedy at Sidelines!

Sidelines Sports Bar & Grill

COMEDY ENTERTAINMENT
Sat, 16 May at 07:30 pm “Supervillains of Comedy May Edition” “Supervillains of Comedy May Edition”

256 Pelissier St

COMEDY ENTERTAINMENT
Sat, 16 May at 08:00 pm Hannah Lawrence LIVE Comedy At Tipsy Toucan (May 16th)

The Tipsy Toucan

COMEDY ENTERTAINMENT

What's Happening Next in Windsor?

Discover Windsor Events