|Philip Seymour Hoffman||Jack|
|Tom McCarthy||Dr. Bob|
|Richard Petrocelli||Uncle Frank|
|Elizabeth Rodriguez||Event Coordinator|
|James P. Anderson||Pool Swimmer|
|Stephen Adly-Guirgis||MTA Worker|
Single Jack drives a limo for a living and has a best friend, Clyde, a married co-worker. Clyde and his wife decide to set up Jack with another friend, Connie . 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.