SINGLE WITH STRANGERS
Saying 'no thanks!' to swiping right, come meet with singles in the city for a night of conversation and mingling, paired with a welcome cocktail and light bites! Hosted by With Strangers creator Jess Janz and community builder Tychon Carter, guests can connect over guided conversations that are designed to move beyond small talk and foster meaningful conversation.
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.
TYCHON CARTER
Tychon's debut as a public figure stemmed from being crowned as the first black winner of Big Brother Canada (Season 9) and competed on The Amazing Race Canada. Now utilizing his background in Urban Planning and experiences dealing with adversity, navigating intergenerational trauma, and confronting the realities of anti-Black racism, Carter-Newman has built a platform that fosters inclusivity to motivate and equip learners to rise above systemic limitations and to face the complexities of mental wellness.
FREQUENTLY ASKED QUESTIONS
WHAT'S THE AGE RANGE?
This particular social is for people in their 20s, 30s and 40s
WILL THERE BE AN
EVEN AMOUNT OF MEN AND WOMEN?
We can’t guarantee the ratio of who will show up, but we aim to get a wide range of ages, genders, and sexualities! We want everyone to have a great night. We find that men are a bit more hesitant to sign up - nudge your friends and tell them to sign up with you!
IS DINNER INCLUDED?
Your ticket includes a welcome cocktail and snacks provided by W Toronto - you'll be able to order drinks (for yourself or for someone you'd like to impress!) at the bar!
Hungry for more? The W’s kitchen is open for orders as well.
We find that men are a bit more hesitant to sign up - nudge your friends and tell them to sign up with you!
WHAT IS YOUR POLICY
FOR CREEPY PEOPLE?
We have a zero tolerance policy for creeps in fact! We take everyone’s safety very seriously, and will be upholding an unwavering ‘Don’t Be A Creep’ policy - anyone violating the safety and comfort of another guest will unfortunately be removed from the event. Sorry not sorry!
EVERYONE WILL BE SINGLE!
That's one of the only rules we have – you must be single to attend.
EVERYONE IS WELCOME!
Whatever your sexuality or gender, we're here to meet great humans who are interested in connecting.
FEEL FREE TO COME
SOLO!
95% of guests come to With Strangers alone, so you'll be in great company!
DIG INTO FREAT QUESTIONS!
Guests will gather for three rounds of small group conversation with questions prepared by Tychon and 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!
CONNECT WITH FELLOW CONSIDERATE
HUMANS!
Whether you end up meeting someone that you want to go on a date with or meet your next pickle ball 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.