Hitch (2005)

Alex “Hitch” Hitchens is a legendary--and deliberately anonymous--New York City “date doctor” who, for a fee, has helped countless men woo the women of their dreams. While coaching Albert, a meek accountant who is smitten with a glamorous celebrity, Allegra Cole, Hitch finally meets his match in the person of the gorgeous, whip-smart Sara Melas, a gossip columnist who follows Allegra’s every move. The ultimate professional bachelor, Hitch suddenly finds himself falling deliriously in love with Sarah, a reporter whose biggest scoop could very well be the unmasking of Manhattan’s most famous date doctor.