Sweetest Day in 2025 is celebrated on Saturday, October 18. It falls on the third Saturday of October each year in the United States. This day is observed mainly in parts of the Midwest and some other states, and it is a time for romantic gestures and acts of kindness, often involving giving candy, small gifts, and cards. Sweetest Day originated in Cleveland in 1921, where candy makers distributed sweets to the less fortunate, and it has grown into a day similar to Valentine's Day in some regions. The date shifts each year but always lands on the third Saturday of October.