Judy Kennedy, 61, is unable to walk because of a neurological disease. She wants romance but is finding it hard to meet new people. Politician Jagmeet Singh, math prodigy Tai Poole and host Sook-Yin Lee help Judy find ways to new connections.

Boy genius Tai Poole is struggling with a problem that he can't quite solve: accepting his ailing grandfather's mortality. Sook-Yin and strangers suggest ways they can stay close and offer insight from their own experiences with death and sickness.

Teen Josis Thomas is set to attend Laurentian University on a scholarship. It is a dream opportunity but he’s worried about leaving behind his beloved Regent Park, making ends meet, fitting in and living up to all his expectations.

Author Sheila Heti is a shining literary light. But it seems the more popular she is, the more detractors there are. She doesn’t want to be paralyzed by online comments, but she refuses to ignore valid criticism

Dr. Jon Fiddler is “a wild child queer kid at heart”, who works on a Pikangikum First Nation reserve. The reservation's living conditions impede his ability to treat those in need. Jon has to decide whether or not he wants to work there.

Alan Zweig is a documentary filmmaker and self-described ‘old dad’. He has major control issues that he's encouraged to let go of at the sleepover. What will Alan hang onto when his problems are unleashed in

Scaachi Koul is an outspoken writer with an undeniably bold presence. As night falls, she reveals the weight of her upsetting personal problem: the deterioration of an important relationship that has turned into a silent standoff. She says it's unsolvable

Charlie McGettigan is eight years old, freckled and fearless. Despite her confidence, Charlie wrestles with a problem that has the kids at school making faces at her. Will strangers Scaachi Koul and Alan Zweig be able to help solve Charlie's troubles?

Sleepover with Sook-Yin Lee finds connections between strangers in a hotel room. It launches June 27. Here's Sook-Yin on what the show’s all about.

Sook-Yin Lee, on a quest for an institution to sleep over in, finds Native Child and Family Services of Toronto, a Children’s Aid Society, where she meets three Indigenous youth. Hear what life is like for them, their experiences and challenges.

Caterina Sinclair (Saulteaux Ojibway Nation, Spawning & Manila, Philippines) spent 6 difficult years in foster care. She’s grounded, smart, resilient, and committed to living healthy. How can she maintain her friendships and stay on her own path?

Tegan Smallwood, 15, isn’t sure which nation she's from because her mom was adopted during the Sixties Scoop. A few years ago, her family went through a rough patch. Now, she wants to unpack it. How can she approach this difficult conversation?

Jordan Lonechild-Lavalley (Plains, Cree & Ojibway, Saskatchewan). Childhood struggles helped build his strong character. Now he wants to be a social worker but can be quick to snap at people. How can he curb his temper and excel professionally?

Perfect strangers sequester themselves for 24 hours to help each other. But what happens when they return to an imperfect world? Sook-Yin Lee checks in with guests from Toronto and Peterborough to find out.

Deep in the Canadian wilderness arrives Trudy Wilson— realtor, long distance swimmer, and devoted mom. Family is important to Trudy, but since her mom’s death, she’s been battling with her big brother. Can strangers solve Trudy’s sibling rivalry?

Orville Thertell -- a typical affable Canadian--might be too nice. Orville’s being taken advantage of, but can’t put his foot down. Sequestered in a boathouse in the woods, can tough talk from a city guy and a realtor help him stick up for himself?

Oseko Ogega is a working class hero with a gift of the gab. He leads a double life, and it’s got him at a crossroads: should he be a working stiff or follow his passion? A rap battle in the wilderness helps unlock the secret of his struggle.

Davinder Mahli, 18, is passionate about theatre, and has written award-winning plays. Davinder’s parents worked hard to send him to theatre school, but his inspiration is slipping. Does he stick it out, or does tell his parents he’s switching majors?

Walter Callaghan is a former military medic, forced out after a serious back injury. Over ten years later, Walter still clings to his military identity and ghosts of the past. Can Walter learn to let go of the guilt he’s been harbouring all these years?

As a “passion coach”, Eryn Faye Frans helps confused Christians navigate sex and intimacy. But for all of her expertise, Erin Faye is struggling with her own problem: after being diagnosed with colon cancer, she's trying to get her own passion back.

In the Sleepover Live Power Nap Edition, three mystery guests meet for the first time in a king-sized bed on stage with Sook-Yin Lee to share their deepest dilemmas.

Hear part two of 'Sleepover Live Power Nap Edition', where three mystery guests meet for the first time in a king-sized bed on stage with Sook-Yin Lee to share their deepest dilemmas.

Sook-Yin Lee checks in with guests from Vancouver, Salt Spring Island, and Toronto after they’ve checked out. The big question remains: Once you return to the world post-sleepover, what happens to your problems?

Judy, the “NO. 1 GRANNY”, sings, dances, golfs, skis, and loves driving. That’s her problem. Her family is worried about her and wants Judy to give up the wheel. Faced with the realities of ageing, should Judy park the car?