An aging virgin decides to attend his high school reunion to win the heart of a girl who never knew he existed. He reunites with his two childhood friends to accompany him to their high school reunion, a divorced stock broker who is contemplating suicide and a bohemian alcoholic musician. Together these three atypical companions embark on their roadtrip, but are thrown wildly off-course through the American landscape and forced to confront their failures and discover the difficult choices they must make to persevere.