The Ostroff and Walling families are best friends and neighbors, living across the street from each other on Orange Drive. Prodigal daughter Nina Ostroff (Meester) returns home for Thanksgiving dinner after a five-year absence, newly broken up with her fiancé Ethan (Rosen). Rather than developing an interest in the successful son of her neighbors, Toby Walling (Brody), which would please both families, it’s her parents’ best friend David Walling (Laurie) that captures Nina’s attention. When the romantic attraction between Nina and David Walling becomes too great to ignore, the lives of the two families are thrown into upheaval. It is not long, however, before the ramifications of the affair begin to work on the other family members in unexpected, hilarious and even positive ways, leading everyone to reassess what it means to be happy, and how to find happiness with, and perhaps in spite of, your own family and friends.