My Life with Caroline is a 1941 American comedy film starring Ronald Colman and Anna Lee in a screenplay by John Van Druten and Arnold Belgard, and directed by Lewis Milestone for RKO Radio Pictures. It was Anna Lee‘s second Hollywood film and her debut in a Hollywood star role.
Wealthy publisher Anthony Mason (Ronald Colman) weds ditsy socialite Caroline (Anna Lee) who sees nothing wrong with chasing men even after her marriage. Caroline flirts with Paco Del Valle (Gilbert Roland) while at a charity ball in Alpine Lodge, Idaho, and Paco then asks Mr. Bliss (Charles Winninger), her father, for permission to marry his daughter. Bliss tells them they need to ask her husband, and Caroline and Paco telegraph Anthony in New York.
As the two reach the Idaho airport and are waiting for an eastbound plane, Mason has just himself arrived. Seeing the two together, he recalls in an involved flashback sequence a nearly identical and complicated situation from two years earlier when his wife was enamored of sculptor Paul Martindale (Reginald Gardiner) in Palm Beach, Florida. Returning to the present in Idaho, Caroline sees Mason’s pilot carrying the bust of her that had been sculpted by Paul Martindale, and follows the pilot to where Mason was waiting.
Martindale, having himself been at the charity ball, finds himself to be a chance spectator of the reunion. He proceeds to the airport terminal, where he joins Mason, Caroline, Bliss, and Del Valle. Caroline blithely tells Mason that she cannot decide now between Del Valle and Martindale, forcing Anthony into a new set of situations where he has to work overtime to win her back.