ISadie Hawkins Day is a rare holiday in that it originated from a cartoon. It began in the 1930's  with Al Capp's "Lil Abner Cartoon. In the cartoon, the mayor of Dogpatch was desperately trying to marry off his ugly daughter.  Having no luck, he created Sadie Hawkin's Day, a day where a race is held and all the single men are given a short head start, but, if a woman catches her man, he had to marry her.

Sadie Hawkins Day races and events grew in popularity during the course of All Capp's long running cartoon. After the cartoon was discontinued (after running 40 years!) the holiday began to decline in popularity although it is still celebrated widely on college campuses.

There is much debate on what actual day in November is Sadie Hawkins Day.  Here are the possible dates:

November 1st:  According to The Charleston Gazzette, The Charleston Gazzette sponsored the first Sadie Hawkins Day on November 1st, 1938

November 9th and 13th:  Although widely celebrated on the 13th  according to the Old Farmer's Almanac, the first Sadie Hawkins Day took place on November 9th, 1938 and states that it is usually celebrated on the Saturday nearest the 9th of November.

November 15th:  Sadie Hawkins Day made its debut in Al Capps Li'l Abner Comic strip in 1937.  It was not Al Capp's intention to have the event occur annually or to have a specific date.