Holly and Gerry are a married couple who live on the Lower East Side of Manhattan. They are deeply in love, but they fight occasionally. Gerry dies suddenly of a brain tumor and Holly realizes how much he means to her as well as how insignificant their arguments were.
Deeply distraught, Holly withdraws from her family and friends until they descend upon her on her 30th birthday. They are determined to force the young widow to face the future and decide what her next career move should be. As they rally around Holly and help organize her apartment, a cake is delivered, and with it is a message from Gerry. It proves to be the first of several meaningful messages — all ending with "P.S. I Love You" — he arranged to have delivered after his death. As the seasons pass, each new message fills her with encouragement and sends her on a new adventure. Holly's mother Patricia believes Gerry's letters are keeping Holly tied to the past. But they are, in fact, pushing her into the future. With Gerry's words as her guide, Holly slowly embarks on a journey of rediscovery.
Gerry arranged for Holly, Denise, and Sharon to travel to his homeland of Ireland. While there, they meet William, a singer who strongly reminds Holly of her deceased husband and, coincidentally, was his childhood friend. During the vacation, Denise announces she's engaged and Sharon reveals she's pregnant, and the news causes Holly to relapse emotionally and once again withdraw into herself out of sadness.
Holly eventually enrolls in a fashion course and discovers she has a flair for designing women's shoes. A newfound self-confidence allows her to emerge from her solitude and embrace her friends' happiness. While on a walk with her mother, she learns that her mother was the one whom Gerry asked to deliver his letters after his death. She takes her mother on a trip to Ireland and, as the film ends, the audience is left with the notion that Holly has opened herself up to the journey that the rest of her life will be, wherever it takes her; she finally abandons her fear of falling in love again.
PS, I Love You Movie Tie-In Edition