SINGLE WITH STRANGERS
Come meet with other singles in the city for a night of conversation, mingling, and great food! Hosted by With Strangers creator Jess Janz, guests will have the opportunity to connect with each other over multiple rounds of guided conversation that gets past small talk and get to know each other in a meaningful way.
Single With Strangers: Queer Date Night
Stay tuned for updates!
JESS JANZ
Jess Janz is a writer, community facilitator, and the creator of Dinner With Strangers, which brings people from different walks of life to share their stories over a meal while skipping all work talk. Her work examines identity, connection, and what binds us all together. Jess has hosted events for Wealthsimple, lululemon, Altea Active Club, The W Hotel, Staub, and Writers Collective of Canada, and runs monthly writing workshops and Poetry Club for her writing community of over 70k people. Her forthcoming book, 'The Table Where We Meet,' will be published by Source Books in March 2026.
WHAT TO EXPECT
100 of Toronto’s coolest people (that’s you) can expect the following at Single With Strangers:
Everyone will be single!
That’s one of the only rules we have – you must be single to enter in.
Feel free to come
solo!
95% of guests come to With Strangers alone, so you’ll be in great company!
Dig into great questions!
Guests will gather for three rounds of small group conversation with questions prepared by Jess - some fun, some flirty, some thought-provoking - to get the stories flowing and get people learning about each other.
Chat with lots of
people!
Because we’ll be switching up our small groups with each round, you’ll be able to meet lots of other guests, perhaps outside of your usual ‘type,’ and maybe get surprised by who you gravitate towards!
Don’t be afraid to
make a move!
None of this make-eyes-from-across-the-room-and-never-introduce-yourself business; ask for someone’s number! Tell someone they’re cute/ funny/ thoughtful! (and practice no-offense-none-taken understanding if they don’t want to give their number to you)
Connect with fellow considerate
humans!
Whether you end up meeting someone that you want to go on a date with or meet your next pickleball partner, Our community-feel events attract a room full of brilliant people who appreciate slower, healthier, kinder approach to dating over the fast & furious modern dating climate singles are up against.