Mr. Belvedere (1985)

S4E1 The Initiation

Kevin has started his college journey and chooses to pledge a fraternity. As part of his initiation, he must wear women's attire and bring the least attractive girl to a frat party. By chance, he encounters a girl he believes fits this description, but he hesitates to hurt her feelings. Unfortunately, he soon realizes that the only way to escape the situation is to be cruel, leaving him feeling cornered and conflicted about the impact of his actions.