Still single seven years after his marriage breakup, John (John C. Reilly) has all but given up on romance. But to his and everyone else's surprise, he manages to meet the gorgeous and spirited Molly (Marisa Tomei) at a party. Their chemistry is immediate but Molly is oddly reluctant to take the relationship beyond John's house. John follows her home and discovers the other man in Molly's life: her son, Cyrus (Jonah Hill). Cyrus is his mom's best friend and will go to any lengths to protect Molly and is definitely not ready to share her with anyone. Soon the two are locked in a battle of wits for the woman they both love - and only one man can be left standing when it's over!