Buddy Amaral (Affleck) is a charming, smooth talking ad executive who is enjoying his successful career until fate steps in and changes everything. In order to make things right and make amends over his guilt from his past actions, he goes out in search of Abby Janello (Paltrow), a single mother of two struggling to make ends meet as a realtor. So he poses as a real estate client in order to get closer to her. Under these false pretenses they become friends and fall in love, and in the end, Buddy knows he must be truthful and confront Abby about his true feelings and his past.