Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.

World War I has left golfer Rannulph Junuh a poker-playing alcoholic, his perfect swing gone. Now, however, he needs to get it back to play in a tournament to save the financially ravaged golf course of a long-ago sweetheart. Help arrives in the form of mysterious caddy Bagger Vance.