Hitch (2005)

Alex "Hitch" Hitchens (Will Smith) is a professional "date doctor" who coaches other men in the art of wooing women.

While coaching one of his clients, Albert Brennaman (Kevin James), who is smitten with a client of his investment firm, celebrity Allegra Cole (Amber Valletta), Hitch finds himself falling for Sara Melas (Eva Mendes), a gossip columnist who is determined to unmask and ruin the so-called "date doctor" after one of his "clients" had a one-night stand with her best friend. Sara doesn't realize that Hitch refused to work with this "pig" and that all of his clients "like women". While Albert and Allegra's relationship continues to progress, Hitch finds that none of his tried and tested methods are working for him, despite being a master of the art. After Hitch is unmasked, he and Sara break up, and Allegra and Albert follow soon. Finally, Hitch confronts Allegra and convinces her to reunite with Albert, before reconciling with Sara. In the process, he makes the startling discovery that he doesn't really do anything significant besides allowing his clients to get the attention of the woman and giving them confidence, and that most of his customers (particularly Albert) really were successful by just being himself. The film ends with Albert and Allegra getting married as well as Alex and Sara resuming their relationship.