Sweetest Day is primarily celebrated in the Midwest and parts of the Northeast. The holiday is said to have gotten its start in Cleveland in 1922 when a candy company employee named Herbert Birch Kingston wanted to bring happiness to those in society who were often forgotten, specifically orphans and shut-ins. He enlisted the help of some friends, and together they handed out candy and other small gifts to those they thought needed them most.
The idea spread, especially in the early 1930s when movie stars Ann Pennington and Theda Bara became involved, according to Hallmark.
That tale, however, was called “entirely fictitious” by a story for The Atlantic, which said that Sweetest Day actually began as “Candy Day” in 1916. Candy Day was established for the sole purpose of selling more candy, and Kingston was actually an advertiser, according to the Atlantic.