Sweetest Day is celebrated on the third Saturday of October each year. In 2025, Sweetest Day falls on Saturday, October 18. This holiday originated in Cleveland, Ohio, around 1921-1922, when candy makers distributed sweets to orphans and those often overlooked in society as a charitable gesture. Today, it is primarily observed in the Midwestern United States and parts of the Northeast, where people express love, affection, and appreciation to loved ones by giving cards, candies, flowers, or small gifts. Sweetest Day emphasizes acts of kindness and romantic gestures, similar to Valentine's Day but with a charitable aspect as well.