Mister Cory

Mister Cory is a 1957 film by Blake Edwards starring Tony Curtis as a con artist who almost reforms. The film was atypical of Hollywood fare of its day, but found favor with avant garde critics, including JeanLuc Godard who praised the film and considered it an influence on his own early work as a filmmaker.

Sabotaging her motorboat as a ploy to get close to her, Cory swims out to help, only to find Abbys kid sister Jen on the boat instead. She volunteers to assist his effort to win Abbys heart.Abby mistakenly believes him to be a guest at the resort. She invites him on a trip to New York, but when Cory tries to raise money at a poker game, a guest named Caldwell cleans him out. Abby is offended when she discovers that Corys only a busboy and walks away for good. ........

Source: Wikipedia