The Breakup Artist (2004)

Jim, 35 and never married, has a drawer full of photos of ex-girlfriends. He'd like permanence, but can't find the right woman. Is it him? He seeks advice from his father, his happily-married brother, his priest, and Teresa, his close friend at the Manhattan celebrity TV show where he works. She's about to marry Tom and is full of opinions for Jim. Three things happen over a day or two: Jim rehearses breaking up with his current fling, he meets a dazzlingly beautiful neighbor, and Tom asks for help telling Teresa his true feelings. Can Jim transform himself from someone who's good at writing break-up lines into someone who can find and express his heart?