Hitch (2005)

Synopsis
A man who teaches dateless wonders how to become irresistible to women learns just how hard it can be to do it yourself in this romantic comedy. When a guy in New York City wants to make the right impression with a certain lady, Alex "Hitch" Hitchens (Will Smith) is the man he calls. Hitch has made a career out of coordinating a man's first three dates so that they'll show him to his best advantage (for a price, of course), and more than a few have taken women to the altar they first started courting with Hitch's help. But Hitch discovers his own romantic limitations when he falls for Sara (Eva Mendes), a journalist who has her own ideas about romance, and might just expose Hitch's underground business to the world. In the midst of all this, Hitch has his hands full with Albert, a sweet but socially inept man who has enlisted Hitch's services. ~ Mark Deming, All Movie Guide