Freshman Love (1931)

In this 100% fictional-plot short a fictional freshman, played by an actor named Don Tomkins), becomes smitten with and writes letters to a singer, Ruth Etting (Ruth Etting), on a fictional radio station. His fictional 1930s nerdy friends take her answering letters in return and torment him about no response. The fictional Ruth Etting (played by the real Ruth Etting) meets him and helps him turn the tables on his tormentors.

Unfortunately the movie Freshman Love is not yet available on Disney Plus.