The first Sadie Hawkins Day was fictionally celebrated in the (questionable) Li’l Abner comic of November 15, 1937 by Al Capp.
Sadie Hawkins was a woman who was in that time called an “spinster” because she was still single at the “old” age of 35.
Being “homeliest gal in all them hills” made her father worried that she would live at home for the rest of her live. So he declared “Sadie Hawkins Day”, rounded up all the bachelors of that town and made them do a foot race with the rule that whomever Sadie would catch, she would enslave marry.
The spinsters of the town decided to have a Sadie Hawkins day every year so they could violate men get married too.
And they all lived…..ehm….not so happily ever after?
Those were stories in times when communication about the importance of consent and personal boundaries was often dismissed a little too easily.
Today these stories have lost a lot of their charm as our collective awareness is outgrowing anti-social behaviours.

The real world implementation of Sadie Hawkins Day is, fortunately, a lot less aggressive.
You could say that the bad ideas were dismissed and the good parts we now use for Sadie Hawkins Day, leaving the name as a mere a tongue-in-cheek joke.
Because of how women are often culturally/traditionally discouraged from taking initiatives in approaching men. Women who do ask men out or even approach them for a flirty talk are often seen as too eager or worse.
On Sadie Hawkins Day women are explicitly allowed to break these obsolete traditions and are actively encouraged to ask men out for a date!
Mind though, that no real chasing, capturing or otherwise restricting behaviour is allowed, unless done with openly enthusiastic consent from the captee, of course.
Who will be your choice of date for Sadie Hawkins Day?

Sources:

• https://en.wikipedia.org/wiki/Sadie_Hawkins_dance
• https://en.wikipedia.org/wiki/Sadie_Hawkins_Day