‍After losing his job as a paralegal, Sam Stein (Matthew Shear, Between the Temples) suffers a panic attack and stumbles into a job babysitting his psychiatrist's three granddaughters. The girls' mother, Dianne (Amanda Peet), is an actor whose once-promising career has stalled; she is now in a difficult marriage to a rock bassist. When her husband goes abroad on tour, Dianne and Sam discover an easy rapport. Sam joins Dianne's family to babysit for the summer on Martha's Vineyard, and he ends up in a house with the woman he pines for, her husband, the three kids, and all four grandparents, including his psychiatrist.