Alex Hitchens (Will Smith) is a famous, albeit anonymous, 'date doctor' who helps men woo their ultimate dream girls. While aiding a shy accountant (Kevin James) with his object of fantasy, celebrity Allegra Cole (Amber Valleta), he encounters gossip columnist Sara Melas (Eva Mendes). Not one easily swayed by the opposite sex, he nevertheless finds himself smitten by the beautiful, smart and sassy reporter. She's the only one able to derail him from his usual smooth romantic ways, and she may be the one to finally unmask his real profession.