My Life with Caroline is a 1941 American comedy film directed by Lewis Milestone and starring Ronald Colman and Anna Lee, in her second Hollywood film and her first in a starring role. The supporting cast featured Charles Winninger, Reginald Gardiner and Gilbert Roland. The screenplay was written by John Van Druten and Arnold Belgard.

Ditsy socialite Caroline, is married to wealthy publisher Anthony Mason.

While alone at a charity ball in Alpine Lodge, Idaho, Caroline flirts with Paco Del Valle, who wants to marry her. Paco asks her father Mr. Bliss for permission to marry his daughter. Bliss tells them that they need to ask her husband, and Caroline and Paco telegraph Anthony in New York.

As Caroline and Paco await an eastbound plane at the airport, Mason arrives. Seeing the two together, Mason recalls a nearly identical situation that occurred two years earlier when Caroline was enamored with sculptor Paul Martindale in Palm Beach, Florida.

In 1940, William Hawks (brother of film director Howard Hawks), along with Ronald Colman, Charles Boyer, Irene Dunne, Lewis Milestone and Anatole Litvak, founded United Producers Corporation. The company intended to make 10 films for RKO, and My Life with Caroline was the first of five that were to star Colman.

The film's screenplay was written by John Van Druten and Arnold Belgard, adapted from Louis Verneuil's film The Train for Venice, which was based upon the play The Train for Venice, written by Verneuil and Georges Berr.

Milestone had tested actresses Miriam Hopkins, Paulette Goddard and Jean Arthur for the role of Caroline but decided on Anna Lee after seeing her in the British film Young Man's Fancy. My Life With Caroline was Lee's Hollywood debut in a starring role.

The film's sets were designed by the art director Nicolai Remisoff.