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2.
Sweetest Day, a pseudo-holiday, is celebrated on the third saturday of every October. It is one of the stupidest things ever. It makes Valentine's day look authentic - at least it's nationally recognized. Sweetest Day exists almost strictly in the midwest, specifically in Chicago.
There's an actual story behind the creation of sweetest day, but no one gives a damn.
by Yavo October 15, 2005
 
1.
Sweetest Day is a holiday celebrated every year on the third of October, primarily only in the Mid-West. Many people refer to Sweetest Day as a "Hallmark Holiday", meaning that it is a made-up holiday, in order for candy, card, and flower stores to increase their profits.

The creation of Sweetest Day is often attributed to Herbert Birch Kingston, a local candy company employee. The first Sweetest Day was October 8, 1921 in Cleveland, OH, where The Sweetest Day in the Year Committee distributed over 20,000 boxes of candy to "newsboys, orphans, old folks, and the poor". It was a generous way to show love and appreciation to the poorer folk, who Kingston felt were neglected by the community.

Nowadays, Sweetest Day is a day to shower the ones you love with gifts and make them feel special, just like Valentine's Day. Even though, many people believe that Sweetest Day is for the guy and Valentine's Day is for the girl, that's not true. It's just another day to show love, respect, and appreciation for family, friends, and loved ones.
*Hands your best friend a box of chocolates*
"Happy Sweetest Day! Thanks for always being there for me. I really appreciate it and I love you dearly."
by AmandaPandaXOXO August 19, 2012
 
3.
Yet another made up holiday invented by Hallmark that gives girls an excuse to whine for more gifts.
My girlfriend won't put out because I forgot about Sweetest Day. What the fuck is that?
by Ryan Sandberg October 26, 2005
 
4.
when a girl pours maple syrup into her vagina and then slowly oozes it out into their lover's mouth
I had the best sweetest day ever last night. Reminded me of 'Nam.
by chang alang October 16, 2010