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

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.

Based on the novel by Edgar Wallace, detectives at Scotland Yard try and track down The Crimson Circle, a secret society of blackmailers

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.

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.