Super nerd woos the object of his affection, is rebuked. The town jock with matching horse (you can see him driving a cool truck or a flashy car) gives him a wedgie (super sized) adding to his humiliation. It is enough for him to skip town.

It is later learned that the nerd left for the city (NYC) and became successful. In a nerdy way.

Sounds like a story from the Techno Boom era (or dot.com.bubble).
But it takes place over 235 years ago.
Ichabod Crane is the name.

Cool!

Was Washington Irving’s story ahead of its time? Or is the story universal no matter the setting?

It also explains away at least one of the supernatural ghost stories going around at the time.

It paints a nice picture of a quaint small town life in New York’s Hudson Valley. A quick read. Well worth the time.