Douglas "Dawg" Munford (Denis Leary) is womanizer who does not care about women he sleeps with and leaves them after having sex. He loses his job but inherits one million dollars from his grandmother. However, the money comes with a catch that he will have to apologise to one dozen women that he had sex with and he will not get it unless they forgive him. His grandmother’s lawyer Anna (Elizabeth Hurley) has to go with him to ensure that the women have actually said ‘I forgive you’. He uses all possible tricks to get the women to forgive him. However, he also realizes that he has affected some of them negatively and his attitude starts changing. Along with that Anna’s feeling towards him also grow.