Alex "Hitch" Hitchens (WILL SMITH) is a self-proclaimed "date doctor" who believes that any man can sweep any woman off her feet as long as they have the right broom. Most of Alex's clients haven't had much luck in the dating world, but he's so good at coaching them that he's never without work, all of which comes from referrals by his satisfied customers.
His latest client is Albert Brenneman (KEVIN JAMES), a somewhat nerdy and slightly clumsy tax consultant for a corporate board that oversees the portfolio of wealthy socialite Allegra Cole (AMBER VALLETTA). Albert is smitten with her, but since she seems so far out of his league, he doesn't think he stands a chance. On the other hand, Alex is confident he can turn Albert into the sort of man attractive to Allegra and thus sets out to work his romantic, makeover magic on him.
When Albert and Allegra show up on the social scene together, that draws the attention of New York gossip columnist Sara Melas (EVA MENDES) whose boss, Max (ADAM ARKIN), wants her to get the scoop on this new relationship. A cynical workaholic, Sara doesn't have time for men -- especially after hearing the daily dating travail of her best friend Casey (JULIE ANN EMERY) -- but has found herself amused by the charms of a smooth and handsome operator who's been putting the moves on her.
Little does she realize, however, that this man -- Alex -- is the person behind her latest pending scoop. As the two start dating and Albert and Allegra's relationship grows, it's only a matter of time before the truth is revealed and everyone must deal with the ramifications of their relationships and work-related efforts.