Wendell Baker is a dreamer and schemer whose latest scam lands him in jail and leaves him alienated from his longtime girlfriend, best friend and even his dog. Eternally optimistic, Wendell makes the most of his time behind bars and vows to turn his life around. Upon release, he gets a job at a retirement hotel, where he befriends some of the colorful residents. Wendell's new friends advise him on how to win back his girl, while he helps them battle...