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.