Sweetest Day in 2023 is on October 21, which is the third Saturday of October. Sweetest Day is a holiday that originated in Cleveland in 1922 when candy companies distributed boxes of candy to the citys vulnerable, including "newsboys, orphans, old folks, and the poor". The holiday is a day to share romantic deeds or expressions, and acts of charity and kindness. Unlike Valentines Day, there is no pressure to do anything elaborate, and people can express love or appreciation towards anyone with a small gift or gesture of kindness. Sweetest Day is not a federally recognized holiday, but it is observed by people in states and regions around the U.S. . The holiday is most popular around Cleveland and Detroit, and it is mainly celebrated in the Midwest, parts of the Northeast, and Florida.