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Insecure Over Wine
WorkCAD 60

Insecure Over Wine

Friday 9 October 2026, 18:00

Venue time (Toronto)

The Annex Hotel · Directions

Friday 9 October 2026, 18:00Venue time (Toronto)
The Annex HotelDirections
CAD 60Tickets sold by luma.com
Sold out — view event pagevia luma.com
Add to calendar

Downloads an .ics file · Times are in America/Toronto · Google Calendar

Hey, how's it going? Insecure Over Wine looks like it should be pretty interesting. Want me to help you organise around it?

Event details

Tickets sold by luma.com

Add to calendar · Downloads an .ics file · Times are in America/Toronto · Google Calendar

Can you believe it’s been 10 years since Insecure first aired? A true classic that somehow never gets old. And since the anniversary tour wasn’t making its way to Toronto, we decided to host our own in collaboration w/ Joelle .
Whether you’re insecure about wine and want to explore it without all the pretension, or you simply want to enjoy Insecure over wine, this one’s for you.
We’ll sip through three wines, revisit three moments from the show, and get into the hot takes, questionable decisions, and conversations that Insecure always seems to bring out.
​What’s Included:
‘We Got Ya’ll’ ​Welcome Drink: A refreshing non-alcoholic drink to kick off the evening.
3 Pour Flight: A curated 3-wine tasting inspired by Insecure with each wine paired to a character or story arc from the show. 3 oz pours.
Non-alcoholic wine option available, courtesy of Acquired Taste
Insecure Screening: Three moments from the show, followed by curated hot takes and conversation.
Sounds from @chiefteef: Because what would Insecure be without the soundtrack?
​Bites & More
We’ve linked up with The Annex Hotel to curate a small bites menu that will be available for purchase throughout the evening.
In the meantime, let's keep in touch 🫶
Instagram: @letslinkup.toWebsite: letslinkup.ca

Tickets are non-refundable but can be transferred to a friend if you're unable to attend.
📸 By attending, you consent to being photographed and/or videographed for event content. Prefer to stay off-camera? Let us know!

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