The Richest Girl in the World (1934)

Titular girl wants to find a guy who loves her for herself, not her money. She decides to test a potential suitor by pretending to be her secretary (and vice versa) and actively encouraging him to woo the supposed richie. I wish it had been a bit lighter as the emotional mindgame felt kind of impossible to put in the past - regardless of whether or not he successfully negotiated the test.

B-