Produced by comedy specialist Harry M. Popkin and his brother Leo Popkin, My Dear Secretary stars Kirk Douglas as Owen Waterbury, a best-selling novelist with an eye for the ladies. When aspiring writer Stephanie Gaylord (Laraine Day) signs on as his secretary, Waterbury assumes that he's lined up another sexual conquest. But Stephanie is not so easily won over, and the rest of the film finds Waterbury striving to come up to her standards. Whenever the film's pace lags, one can count on the farcical expertise of Keenan Wynn, borrowed from MGM to play Douglas' sardonic confidante, to save the day. Along with Strange Love of Martha Ivers, My Dear Secretary is one of the most accessible of Kirk Douglas' early films thanks to its public-domain status.
~ Hal Erickson, All Movie Guide