Movies and TvShows featuring "old-man-flirts-with-a-young-woman" theme.

Marie Devere and Helen Gray are two sophisticated, gold-digging chorus girls on the look-out to marry a rich man, who measure the men they meet by their Bradshaw ratings. They befriend Lettie Crain, a country girl who comes near being deceived by Bartley Mortimer, a rich playboy. She is saved by another girl, Cynthia Kane, whose life Mortimer has ruined, and Lettie finds happiness with Bob Garrett, a poor but honest working man.

A gold-digging woman wins a big settlement against an older married man, which threatens to destroy the man's family. His son, discovering that the woman is part of a ring of blackmailers and that she is planning to flee the country, takes along his hulking chauffeur and follows her onto an ocean liner. There the two pretend to be a pair of wealthy playboys so that the woman will make a play for him and try to blackmail him, too, so he can then expose her and prove his father's innocence. Complications ensue.

The Pest (aka The Freeloader) is a 1917 silent comedy film featuring Oliver Hardy and starring Billy West in one of his "Charlie Chaplin" rip-off roles.