The Oranges (tt1313139), Ostroff and Walling families are not only closest friends but also neighbors living across each other on Orange Drive. Nina (Leighton Meester), the extravagant daughter of the Ostroff family, has just broken up with her fiancé Ethan (Sam Rosen) and returned home for Thanksgiving dinner. While her family wants her to be interested in Toby Walling (Adam Brody), the successful son of their neighbors, Nina becomes attracted to David Walling (Hugh Laurie), her parents' closest friend. As the romantic attraction between Nina and David becomes noticeable to others, the lives of the families are thrown into chaos. Soon, this relationship brings about unexpected, even comedic and positive effects on the other family members. Through this, the meaning of finding happiness against the expectations of family and friends is reevaluated.