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Although Sweetest Day has its roots in random acts of kindness, it has evolved into a second Valentine’s Day.  The Sweetest Day Foundation was the idea of Cleveland fashion model Raina Tiffiny.


The mission of the Foundation is to support the original intent behind the first Sweetest Day: to spread joy and love to underprivileged children throughout the country. Much like the first Sweetest Day started in Cleveland, the Foundation is starting with distributing gift bags to children in Cleveland in 2023. These gift bags will be distributed by members of the fashion community as Sweetheart Ambassadors.


The goal for 2024 is to give gift bags to children in every shelter in the greater Cleveland area. The goal for 2025 is to expand to all shelters in Ohio, and eventually all over the country.

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Sweetest Day has been celebrated for over 100 years. It started in 1921 when Herbert Birch Kingston decided to bring a little happiness into the lives of orphans, shut-ins and others who were often forgotten. With the help of  friends, he delivered candy and small gifts to Cleveland’s underprivileged.


On the very first Sweetest Day, an actress passed out boxes of candy to 2,200 Cleveland newspaper delivery boys to express gratitude for their hard work. Another actress passed out 10,000 boxes of candy to patients in Cleveland hospitals.


Sweetest day is celebrated on the third Saturday of   October. The holiday’s popularity is growing so fast that American Greetings and Hallmark now produce hundreds of different greeting card designs for Sweetest Day. 


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