A lifelong womanizer (Doug 'Dawg' Munford, played by 'Denis Leary') learns upon his grandmother's death that he stands to inherit her full fortune - that he was unaware she had accrued - pending his fulfillment of conditions set forth in her last will & testament, according to her strikingly beautiful, savvy attorney ('Anna Lockheart', played by Elizabeth Hurley), who would be charged with accompanying him on his journey in order to ensure he properly & honestly accomplishes the "mission", which is to locate and elicit forgiveness from 1 dozen of his former conquests, if he chooses to accept it.