He's very good at being a very Bad Boy. Successful, egotistic Doug Menford is long on charm, but short on class. Nicknamed Dawg by his college pals, Doug's world is turned upside down when he meets Anna Lockheart who teaches the Old Dog a lesson he'll never forget. A tough as nails attorney and the executor of Doug's grandmother's will, Anna informs Doug that before he inherits the million dollar estate, he must track down a number of women he's betrayed and convince them to pardon his past discretions! With Anna as his sitness, Doug revisits his ex-lovers. Two opposites forced together, anna and Doug are off on a quest to find forgiveness. Along the way, they might just find love.