High school teacher Kristin Caine has a black belt in settling for less and a dying mother who doesn't mince words when it comes to voicing how disappointed this makes her. But when Kristin's status quo is rocked by an unexpected pregnancy and the consequent breakup with her less-than-enthusiastic boyfriend, things change. Suddenly, agreeing to help her overbearing mother complete a bucket list before the big C wins seems not the worst thing in the world-despite their many differences and Kristin's fear of traveling.

But Kristin's sense of self-preservation is strong, and if not for the compassion of Lily Landon, a friendly airport stranger with a tissue to spare, the first leg of the trip might have been over before it even began. Lily is like no one Kristin has ever met-a globe-trotting photographer full of joie de vivre who is on a first-name basis with the flight crew-and in her presence, the impossible suddenly seems... well... possible.

As a journey of physical and emotional adventures, belated mother-daughter bonding, and unexpected romantic feelings for Lily ensues, Kristin must challenge preconceived notions of motherhood, love, and what it means to live life fully, one bucket-list checkmark at a time. Only if she succeeds will she be able to create a new future free of self-imposed limits, for herself and her unborn child.