Wendell Baker (Luke Wilson) is a dreamer and schemer whose latest scam lands him in jail and alienates him from his longtime girlfriend (Eva Mendes). 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 residents. Wendell's new friends advise him on how to win back his girlfriend, while he helps them battle the hotel's evil head nurse (Owen Wilson).