Jack Goes Boating is a 2010 romantic comedy drama directed and starred in by Philip Seymour Hoffman and based on a play written by Robert Glaudini. Jack (Philip Seymour Hoffman) is a slacker who works as a limo driver in Manhattan. Most days Jack can be found smoking joints in between driving jobs or lazing around at his home. However, Jack gets a new outlook on life when he has a chance encounter with Connie (Amy Ryan), an awkward young woman who appears to have an interest in Jack. Jack's friends, Clyde (John Ortiz) and Lucy (Daphne Rubin-Vega), are happy that Jack wants to turn his life around in order to impress Connie. Unfortunately, as Connie and Jack get closer the marriage between Clyde and Lucy does not fair as well. Can Jack begin a promising relationship with Connie when his best friend could be nearing the end of his marriage?