Connor Mead (Matthew McConaughey) é um fotógrafo de celebridades que coleciona ex-namoradas. Acreditando que a vida serve apenas para se divertir e namorar, Connor não entende como alguém pode ter um relacionamento duradouro. Quando seu irmão Paul (Breckin Meyer) se casa ele reencontra Jenny Perotti (Jennifer Garner), a única mulher pela qual realmente se envolveu. À noite ele recebe a visita do tio Wayne (Michael Douglas), um playboy dos anos 70, que lhe diz que receberá a visita dos fantasmas de três ex-namoradas. Através delas Connor percebe as falhas de seus relacionamentos anteriores.

Connor Mead (Matthew McConaughey) is a notorious photographer who has a bad boy reputation of loving beautiful women and dumping them when they fall in love with him. Beautiful models and celebrities flock to his studio to get their picture taken, usually in lingerie, and throw themselves at him. Conner is so overloaded with women that he has to breakup with three women at the same time during a conference call in front of his next prey. His brother Paul (Breckin Meyer) is about to get married, and Connor thinks he is making a terrible mistake. As an incorrigible bachelor, Connor loves his freedom more than ever settling down and loving only one woman. Connor tries to talk Paul out of getting married, and it looks like Connor is about to succeed. Then the night before the wedding, Connor is visited by three ghosts, who take him back to his past, present, and his lonely future. They try to discovery the point in time where Connors became this womanizing jerk. Maybe there is still time to change him into a sensitive, feeling, and caring person that he once was, and he may even find his true love.