Olivia Justice is trying to get back to real life after appearing on a reality dating show. She needs a job to support her mother's long-term care and after no luck with openings in a hair salon, she accepts a position as a nanny—at the summer house her parents used to own. The one good thing is that her best friend, Ella, will be there—along with Ella's older brother, the guy Olivia has carried a torch for since she was a teenager.
After a failed proposal, Dawson Holt heads to Nantucket to refocus on what he wants from life. With his sister's wedding on the horizon, he realizes how lonely life has become. When he reconnects with Olivia, he starts to see that maybe things worked out for a reason after all.
When his ex-girlfriend shows up with his grandmother's ring on her finger and claims she now wants to marry him, will Dawson and Olivia be able to conquer the past and move towards the future?