Carter (ADAM BRODY) is an aspiring screenwriter living in L.A. When his beautiful, famous actress and Gap model girlfriend Sophia (ELENA ANAYA) drops him, he seeks solace in suburban Michigan, where he goes to look after his aging grandmother Phyllis (OLYMPIA DUKAKIS).
Here he meets her neighbors, a beautiful wife and mother named Sarah (MEG RYAN), currently struggling with her typically resentful and rebellious teenage daughter Lucy (KRISTEN STEWART). Soon after Carter arrives, Sarah learns she has breast cancer, which makes her feel more urgent about repairing the relationship with Lucy and ensuring that her younger daughter, Paige (MAKENZIE VEGA) feels secure.
Sarah has her own reason to feel insecure, as her husband, Nelson (CLARK GREGG), has been having an affair. He believes she doesn't know, and she believes Lucy doesn't know, but they all know. Worse, Sarah and Lucy each confide in Carter, swearing him to secrecy concerning their deepest worries and desires. He accommodates them, because he believes himself to be a "great listener." Eventually, Carter comes to terms with his own insecurities as well.