Now or Never celebrates ten years of diving in with people as they gather the courage to take a leap into the unknown, with a live show from Winnipeg's Gas Station Arts Centre!

There are always surprises in a Now or Never story, and this live show is no exception. Secret guests, a pop-up choir, confetti cannons and one hilariously unfiltered kookum who you don't want to miss.

Winnipeg couple Trish Cooper and Sam Vint’s life together has been filled with hilarious and surprising (mis)adventures, including culture shock on the rez, a surprise gummy overdose, and discovering your partner is an accidental fugitive. After 23 years together, can Sam pull off a surprise for Trish live on stage?

Musician Boy Golden shares songs from his new album, and a truly jaw-dropping story from the road.

Now or Never all-star Vivian Ketchum is back for a record fifth appearance on the show and this time it's unhinged. We were there when she graduated high school at 58, sat on her bed as she shared the residential school memories that keep her up at night, and joined her at the post office opening letters from Canadians across the country sharing their reconciliation commitments. What is Vivian up to now? Dating! Hear her raw and unfiltered takes on sex and dating in her sixties.

Two months ago, Jo Dworschak quit her job to follow her dream of being a full-time storyteller and comedian. She joins us on stage to share how fixing a broken elevator in a bathing suit at 17, lit the spark for the life she’s living today.

Hundreds of Canadians have shared their stories on Now or Never over the years. Can Ify and Trevor remember them all? We challenge them with a game of "Guess the Guest," as past guests pop up on stage with three clues, while a blindfolded Trevor and Ify try to figure out who they are.

Plus, Ify and Trevor try their best to surprise each other.

This episode originally aired in April 2026.

An estimated four million Canadians currently live abroad. So what compels someone to ditch their life in Canada and start over somewhere new? From Bogotá to Tokyo, Cape Town to València, Now or Never crisscrosses the globe with expats living out some big, bold adventures right now.

Joshua Will dreamed of living in Japan since he was 14-years-old, so when he got a job with the Japan Exchange and Teaching Programme (JET) he was ecstatic. But he never expected to find himself on tiny Yuge Island, navigating the wild world of Japanese real estate, and renovating a 100-year-old house with no experience and few language skills.

At age 75, Janet Skog-Reid moved to Spain with her children and grandchildren. But when they returned to Vancouver, Janet decided to stay. How this grandmother who spent her life caring for others, is now chasing a life that is finally her own.

When Calgarian Aaron Cresswell bumped into Laura Fajardo at a crowded bar in Bogotá, the two instantly hit it off — so much so, that he ended up moving to the country to be with her. But it soon sunk in that while Aaron found his forever person, he definitely didn’t find his forever home in Colombia.

Barb Deck is no stranger to intense situations — when she’s at home, she’s a pediatric ICU nurse at Sick Kids in Toronto. But since joining Médecins Sans Frontières, Barb spends most of her time tackling even bigger challenges, flying to conflict zones around the world to help deliver care.

Four months ago, Chloe Wilde and her partner quit their jobs, sold their Toronto home, and bought a one-way ticket to South Africa with their two-year-old son. Chloe tells us why she feels a responsibility and pressure to live a "big, bold life," and what it's really like backpacking with a toddle

This is an encore presentation of Now or Never. Season 11 starts September 10

In a world full of dating apps you might be wondering, “Does anyone meet in real life anymore?”

Today we're revisiting a previous episode of Now or Never about people looking for love without the swiping because as more Gen Z and Millennial daters turn away from dating apps and report ‘swipe fatigue,’ people are looking to find love in the wild again. The problem is, we’re a little rusty. So on this episode, Now or Never takes you into some real-life dating stories as people take the first tentative steps to find love IRL.

What better way to boost your dating profile than having your friends hype you up to a crowd of fellow singles? That's the idea behind Pitch-a-Friend nights, where people pitch what makes their single besties so awesome in a five-minute PowerPoint presentation. We crash a Pitch-a-Friend night in Edmonton to find out if any real-life connections are made.

When Lisa Cordileone’s marriage ended 11 years ago, she headed online looking for connection, but apps proved a bust. Trying to date in her small-town in northern Manitoba also made things tough. So last year, she moved to Winnipeg hoping to expand her dating pool. Now, for the first time, she’s putting herself out there at a singles event at a Winnipeg pool hall, and we get to tag along.

Stella Isaac is embracing solo dating. She's open to partnership, but the online and in-person experiences she's had as a dark skinned Black woman in Toronto have made that difficult. Stella invites us along for one of her solo date nights to talk about why these dates have served as the best form of self-care.

Single dad Richard Kemick is looking to dip his toe into the dating world again. There’s just one problem. His living situation is a little…complicated. And tough to sum up in the six minutes he has to make a good first impression at a speed-dating event in Vancouver this weekend. So Ify does a few practice runs with Richard on his opening lines, and finds out why it's so important for him to disclose everything on a first date.

After struggling on the dating apps, 29-year-old investment advisor Kyle Long is breaking out of his shell and trying to find love on the dance floor at salsa class – despite being a self-described introvert with two left feet.

And an update with Victoria real estate agent Krista Nugent, who made headlines last year for a dating application she posted on her Instagram that said, like any realtor, she was open to referrals. Did she end up finding the one?