Overachieving actress, Rebecca (Moore), must come to grips with her failing marriage to stay-at-home dad, Tom (Duchovny). While Rebecca’s slacker brother, Tobey (Billy Crudup), can’t seem to commit to his aspiring-novelist girlfriend, Elaine (Maggie Gyllenhaal). As both relationships spin out of control, the two couples embark on a quest to rediscover the magic and romance of falling in love in New York.

During his twenties, a young man works at various homeless shelters in Boston, where he often intersects with his brilliant but troubled father.