Bob is quite familiar with the art of using a go-between and prefabricated breakup lines to end a relationship. Having been dumped himself by his girlfriend’s intoxicated friend, Jill, Bob decides to make a career out of delivering break-up-o-grams to others. Jared, bewildered on how to break-up with his crazy girlfriend, turns to Bob for help. But, this break-up has something else in store for Bob. . . her name is Natalie.