Jack Goes Boating is a 2010 romantic comedy film directed by Philip Seymour Hoffman, and starring Hoffman in the title role, as well as Amy Ryan, John Ortiz, and Daphne Rubin-Vega. Jack (Philip Seymour Hoffman) is a shy limousine driver who lives with and works for his uncle. His best friend and fellow co-worker Clyde (John Ortiz) and Clyde's wife Lucy (Daphne Rubin-Vega) set up a dinner date at their house for him to meet Lucy's new co-worker, Connie (Amy Ryan) who has some minor intimacy issues of her own. As Jack and Connie get to know each other, he sets his sights on learning to swim so he can take her boating when summer comes. With Clyde eager to help him learn, they begin swimming lessons. Jack decides that summer is too far away to wait for a date with Connie.