Two hapless waiters in a tavern on the Spanish Main play cupid between aristocratic Lady Jane and tavern co-worker Bruce Martindale, but the two bumpkins mix-up a love letter with Captain Kidd's treasure map of Skull Island, leading to them being kidnapped and taken off to the notorious pirate's island.

After a brief encounter with the romantic and thrice divorced Kenneth Marquis, Corliss Archer decides to write in her diary that they are together in order to make her boyfriend Dexter jealous. Corliss' father had also served as attorney representing Kenneth Marquis' ex-wife during his most recent divorce trial. When Corliss and Dexter don't come home one evening until five in the morning, Corliss decides to pretend to have amnesia to avoid the inevitable punishment awaiting her.