Single Jack (Philip Seymour Hoffman) drives a limo for a living and has a best friend, Clyde (John Ortiz), a married co-worker. Clyde and his wife decide to set up Jack with another friend, Connie (Amy Ryan). Jack and Connie hit it off, and a tentative romance blossoms, inspiring Jack to take cooking lessons, learn to swim, and apply for his dream job. However, as that relationship grows stronger, Clyde and his wife find their marriage crumbling.