The Sweetest Day Foundation was the brainchild of Cleveland model Raina Tifffiny. The mission of the Foundation is to promote the Cleveland origins of the Sweetest Day holiday as a time to bring joy, happiness, and love into the lives of the less fortunate. On Sweetest Day, models serving as Sweetheart Ambassadors distribute Swag Bags filled with sweets and goodies to children in homeless shelters and seniors in nursing homes. Funds raised from this event will fund the 2024 Sweetest Day outreach program.