GET TO KNOW
WITH STRANGERS.
We’re all more reachable than ever, so how do we learn how to reach for each other?
With Strangers brings people together to connect beyond small talk. Through shared meals and local meetups, folks are invited to share their story, get curious about each other, and find inspiration through community.
With Strangers began in 2017 as a grassroots dinner series hosted in Toronto by Jess Janz and her friend Ryan Cantelon. The night had just one rule: no work talk allowed. Taking that default question off the table encouraged people to get real and dig down to the juicier stuff. Since those early days, Jess has witnessed more than 900 strangers form real connections in real time.
Today, the With Strangers universe has expanded into a mix of one-of-a-kind gatherings, all designed to help people connect on a much more interesting, fundamental level. From the flagship event, Dinner with Strangers, to the eclectic events of IRL with Strangers, these experiences make room for people to share where they come from, what they’re learning, and what’s important to them.
Let’s stop being strangers and start being With Strangers.
-
![]()
Dinner With Strangers.
brings people together for a night of intentional conversation in unconventional spaces over a beautiful meal. With the only rule being no work talk, join a guided discussion about the good, gutsy stuff of life, like where we come from, what we’re learning, and what we care about.
-
![]()
IRL With Strangers.
IRL With Strangers is a monthly initiative that brings people together to connect within the community.
From yoga classes, spin classes, art gallery openings, wine tastings, poetry readings, market meet-ups and park hangs, IRL With Strangers takes events one step further to create opportunities for connection while trying something new, all while partnering with businesses in the city that care about the bold pursuit of making our community a more connected place.
-
![]()
Workshops and Retreats.
Jess hosts Poetry Club and In Good Company (a drop-in writing workshop) for her writing community on Substack; she regularly hosts month-long creative writing workshops, how to host intentional dinners, and how we can ask better questions.
She’s hosted destination writing and community retreats at Wolfe Island, Ontario, and in Nosara, Costa Rica, and can’t wait to share where she’s headed next.
-
![]()
Event & Group Facilitation.
In addition to hosting over fifty Dinner With Strangers events, Jess regularly facilitates events and guides conversations about what it means to introduce ourselves, what makes a great question, what it’s like being an artist (and accidental entrepreneur!) in the word, and how we can connect with each other.
Most recently she’s hosted a panel for The W Hotel’s ‘What She Said’ initiative for International Women’s Day in 2024; she facilitated a conversation with fellow author (and dear friend) Joél Leon in Brooklyn, NY, and facilitated events for Wealthsimple, lululemon, Staub, and Altea Active Club.
MEET JESS.
Jess Janz founded With Strangers to inspire real conversation and storytelling between strangers. As a writer and community facilitator, she has a passion for people who care about connection, intentionality, and a bold pursuit of creating a better world.
Jess has hosted custom events for Wealthsimple, lululemon, Altea Active Club, The W Hotel, Staub, and Writers Collective of Canada. She also hosts In Good Company and Poetry Club, monthly virtual events for her writing community.
Her work examines identity, connection, and the things in life that bind us all together, and she is currently writing her first book, which will be published by Source Books, in March 2026.
She can’t wait to meet you.