The romantic escapades of two couples: a successful actress (Julianne Moore) and her stay at home husband (David Duchovny); and her slacker younger brother (Billy Crudup) and his aspiring novelist girlfriend Maggie Gyllenhaal). The film follows these four on their pointed, often surprising and frequently hilarious search for love in the midst of careers, family, infidelity and the ever-daunting search for Manhattan street parking.