In 1953, aging socialite Anne Deveraux (RENEE ZELLWEGER) comes home to her Manhattan apartment to find Dan (KEVIN BACON), her bandleader husband, cheating on her with a much younger woman. Fed up with his philandering ways, Anne decides to leave him and take her two sons, George and Robbie (LOGAN LERMAN and MARK RENDALL) on the road.
The trio stops in such cities as Boston, Pittsburgh and St. Louis. Anne remains on the hunt for her next husband, a man who will take care of them all. George laments his mother's wayward ways and wants only to return to Radford University. Robbie, a closet homosexual, dreams of making it as an actor in Hollywood.
None of the cities work out for the Deverauxs. Anne meets a string of men who turn out to be horrible choices. Among them are Harlan (CHRIS NOTH), a career military man who dislikes George and Robbie and tries to control Anne's every move; Wallace (STEVEN WEBER), a former admirer who begs her for a large sum of cash to rescue his finances; and Bill (DAVID KOECHNER), a charming store owner who has a habit of proposing to multiple women even though he is already married.
At one point, Anne's flirtations are even mistaken for prostitution solicitation, and she is arrested. Dan keeps popping in and out of their lives, trying to reconcile but remains unwilling to change. Eventually, Anne decides to take Robbie to Hollywood.