Jack Goes Boating is a 2010 romantic comedy film from Overture Films and Relativity Media. Philip Seymour Hoffman makes his directorial debut as he stars alongside Amy Ryan, John Ortiz, and Daphne Rubin-Vega. The film's script was adapted by Robert Glaudini from the 2007 play entitled Jack Goes Boating which he also wrote. The film premiered at the 26th Sundance Film Festival and was later released in the United States on September 17, 2010. 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...