Dan Burns (STEVE CARELL) is a popular family advice columnist in the local paper, but his personal life is less than perfect. A widower for four years, he's yet to get back into the dating scene, but his hands are full with his three daughters. While the youngest, Lily (MARLENE LAWSTON), doesn't test his patience, his oldest, Jane (ALISON PILL), is frustrated that he won't let her drive, while middle daughter, Cara (BRITTANY ROBERTSON), is upset that her dad won't let her date the boy of her dreams.
Accordingly, there isn't much family love as they head off to the Rhode Island home of Dan's parents, Nana (DIANE WIEST) and Poppy (JOHN MAHONEY), where the rest of the extended family has also gathered. Everyone is concerned about Dan's social life, so they're excited when he tells them about a woman he just met at the local bookstore while out for the afternoon. While she's just started a new relationship, he thinks he's experienced love at first sight. Before he can say anything else about her, however, he finds out much to his shock that Marie (JULIETTE BINOCHE) is dating his brother, Mitch (DANE COOK).
She's just as shocked as Dan and the two try to keep their meeting and feelings toward each other secret. Yet, as Dan grows increasingly frustrated by having her so close and yet so far away, and as Marie becomes jealous when Dan is set up on a blind date with Ruthie (EMILY BLUNT), a former neighbor turned plastic surgeon, the two must decide what to do about their unique predicament.