P.S. I Love You (2007)

Role: William Gallagher

P.S. I Love You is a 2007 American drama film directed by Richard LaGravenese. The screenplay by LaGravenese and Steven Rogers is based on the 2004 novel of the same name by Cecelia Ahern. The film is dedicated to the memory of producer Molly Smith’s sister Windland Smith Rice.

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 suddenly dies 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 prod the young widow to face the future and explore what her life choices 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” — which he had arranged to have delivered to her after his death. As the seasons pass, each new message fills her with encouragement and sends her on a new adventure. Holly’s mother believes that 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 and her friends 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. He then dedicates a song to her but on hearing it, she leaves the place because it was Gerry’s song for her. During the vacation, while on a fishing trip the three women get stuck in the middle of a lake without any oars to row their boat with. At that moment, Denise announces she’s engaged and Sharon reveals that she is pregnant. This news causes Holly to relapse emotionally and again withdraw into herself. They are eventually rescued by William and he decides to spend the night with them. That night, William and Holly get involved physically and Holly tells him about Gerry’s family when William reveals he is actually Gerry’s childhood friend. This causes Holly to freak out, but William calms her down and starts to tell stories about his and Gerry’s childhood. The next day, Holly visits Gerry’s parents and while there, she also receives a letter from Gerry reminding her of their first meeting.

Holly eventually enrolls in a fashion course and discovers that she has a flair for designing women’s shoes. A new found 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, it appears that Holly has opened herself up to the journey that the rest of her life will be, and wherever it takes her; she finally abandons her fear of falling in love again.