Holly (Hilary Swank) is mourning her recently deceased husband, Gerry (Gerard Butler), with her friends Denise (Lisa Kudrow), Sharon (Gina Gershon), and her mother, Patricia (Kathy Bates). Prior to his death, Gerry wrote a series of letters, to be delivered at certain times, to help Holly to move on. Meanwhile, Daniel (Harry Connick Jr.), the bartender of Patricia’s bar, starts to develop feelings for Holly.
One of the letters asks Holly and her friends to visit Ireland, Gerry’s homeland, which happens to be the place where Holly and Gerry met. During that time, it was revealed that Denise is getting married and Sharon is having a baby with Gerry’s business partner. Holly proceeds to hook up with a local named William, who turns out to be a childhood friend of Gerry’s.
Back home, but still unable to move on, she proceeds to ask her mother for advice. Patricia has issues of her own, since her husband abandoned her, and she was not too fond of Gerry when he was alive. However, It turned out that Gerry worked with Patricia prior to his death to get the letters sent out, and Patricia hands Holly his final letter. Holly proceeds to have Daniel read the letter to her at Yankee stadium, and she finally feels that Gerry is gone. Holly and Daniel kiss, but it turns out that they have no chemistry together; they vow to be friends.
The movie ends with Holly taking her mother to Ireland to visit Gerry’s parents.