Gwen Cummings (Sandra Bullock) spends her nights in a drunken haze with her boyfriend, Jasper (Dominic West). She ruins her sister (Elizabeth Perkins) Lily’s wedding by showing up late and disheveled, delivering a drunken, rambling speech, and knocking over the wedding cake. Intoxicated, Gwen steals a limousine from the reception, tries to locate a cake store, and winds up losing control of the car and crashing into a house. She is given a choice between 28 days in jail or in a rehab center, and she chooses rehab.
Gwen is introduced to a variety of patients while in treatment: Oliver (Mike O’Malley) (a hypersexual cocaine addict), Daniel (Reni Santoni) and Roshanda (Marianne Jean-Baptiste) (alcoholics), Bobbi Jean (Diane Ladd) (an older addict), Gerhardt (Alan Tudyk) (a gay man whose addiction is not specified), and Cornell (Steve Buscemi), the rehab facility’s director (a recovered drug addict and alcoholic). Her roommate is young Andrea (Azura Skye), a heroin addict who sporadically self-harms and is a fan of the fictitious soap opera Santa Cruz.