Week end in Havana (1941) John Payne, Alice Faye

In order to get stubborn salesclerk Nan Spencer (Alice Faye) to sign a claim waiver when the company cruise ship that she s on runs aground, Jay Williams (John Payne) agrees to allow her to continue on her longplanned vacation to Havana. Jay accompanies her, but Nan finds his stuffy manner boring, and is charmed by slick Monte Blanca (Cesar Romero). To keep Nan happy, Jay pays off Monte s gambling debt and also agrees to manage his fiery and jealous singer girlfriend (Carmen Miranda).