Henry Aldrich Plays Cupid is a 1944 American comedy film directed by Hugh Bennett and written by Muriel Roy Bolton and Val Burton.

The film stars Jimmy Lydon, Charles Smith, John Litel, Olive Blakeney, Diana Lynn and Vaughan Glaser.

[1][2] Henry plays matchmaker for Mr. Bradley (Vaughan Glaser), his principal and botany teacher at Central High, figuring that marital bliss might mellow the gruff educator and make it easier to get a passing grade and graduate.

Bringing a woman into Bradley's life proves to be complicated, made more so by Mrs. Terwilliger (Barbara Jo Allen), a conniving spinster.

Barbara Jo Allen (also called Vera Vague) "cavorts along with the Aldrich family to add to the merriment", the Kentucky newspaper said.