Giving It Up (1999)

Meet Ralph, charismatic New York adman about town. Encouraged by his sexist boss and unlucky-in-love buddy Peter, Ralph’s life revolves around the pursuit of the opposite sex. Enter his match, smart and beautiful account executive Elizabeth, who is put off by his sex-obsessed ways, convincing Ralph to see a therapist. Just when a relationship between the two begins to flourish, Ralph gets thrown together with supermodel Amber. Now Ralph has to decide whether to change his player-like ways or risk losing the one woman he truly loves.