At thirty-eight years old, Ruthie finds herself newly unemployed, freshly single, sleeping on a friend's couch and downing a bottle of wine each night. Having overstayed her welcome and desperate for a job, Ruthie responds to David's ad: he's looking for someone to drive his aging mother, Kay, and her belongings from PEI to Vancouver. Ruthie thinks it's the perfect chance for a brief escape and a much-needed boost for her empty bank account.

But once they're on the road, Kay reveals that she's got a list of stops along the way that's equal parts sightseeing tour, sexual bucket-list, and trip down memory lane. As David prods for updates and a speedy arrival to his home in Vancouver, Kay begins to share details about a long-lost love and Ruthie takes a detour to play matchmaker, but finds herself caught up in a web of well-intentioned lies.

With the road ahead uncertain, and the past and present colliding, will Ruthie be able to forge a new path? Heartfelt and humorous, The List of Last Chances follows a pair of reluctant travel companions across the country, into an unexpected friendship, new adventures, and the rare gift of second chances.