Sweetest Day is an informal holiday celebrated in the Midwestern United States, parts of the Northeastern United States, Arizona, and Florida on the third Saturday in October. It is a day to share romantic deeds or expressions, and acts of charity and kindness. Sweetest Day has also been referred to as a "Hallmark holiday" or a "concocted promotion" created by the candy industry solely to increase sales of sweets.

The first Sweetest Day was on October 10, 1921, in Cleveland. The Cleveland Plain Dealers edition of October 8, 1922, which chronicles the first Sweetest Day in Cleveland, states that the first Sweetest Day was planned by a committee of 12 confectioners chaired by candymaker C. C. Hartzell. The Sweetest Day in the Year Committee distributed over 20,000 boxes of candy to "newsboys, orphans, old folks, and the poor" in Cleveland.

Although Sweetest Day is still most prevalent in the Great Lakes region where the holiday originated, including Illinois, Indiana, Michigan, Ohio, and Wisconsin, it has spread throughout the country. Celebrations are similar to Valentine’s Day with the most popular gifts being cards, flowers, and sweets. The holiday is not aimed specifically toward any gender, as it was started to give chocolate and sweets to the vulnerable in the city. Now, its seen as a chance to express love or admiration for the people in your life, whether its family, friends, romantic partners, or anyone else.