Irishman Gerry Kennedy (Gerard Butler) and Holly (Hilary Swank), are a happily married couple living in Manhattan. Except Holly wants a larger apartment for when they decide to have a baby. Gerry wants a baby now, and after they fight one night about this, they make up and Gerry makes her laugh. Gerry dies of a brain tumor, and Holly is devastated. The grieving young widow and her friends begin to periodically receive letters written by Gerry while he was alive, each containing a task for Holly to complete, intended to ease her out of her grief and transition her into a new life. One "task" is for Holly and her two friends to go on holiday in Ireland, where the couple first met. On this trip, she hooks up with a singer from a local pub who ends up being one of Gerry's old friends.While she is in Ireland she visits Gerry's parents and visits the spot where the couple first met, and in the process, finds out that she can move on and live life. At the end of the film it is revealed to Holly and the viewer that when Gerry knew he was going to die he wrote the letters and gave them to Holly's mother, and that he made her promise to send them one by one to Holly.