Sweetest Day

Name: Sweetest Day Mug
Brand: Urban Dictionary
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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."

Sweetest Day by AmandaPandaXOXO August 20, 2012

Words you can keep

sweetest day

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.

sweetest day by Yavo December 28, 2005

sweetest day

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?

sweetest day by Ryan Sandberg October 27, 2005

sweetest day

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.

sweetest day by chang alang October 18, 2010

endwarfins

The rush of neurotransmitters and neuropeptides triggered specifically by watching the Seven Dwarfs march home singing "Heigh-Ho" — that particular high of pickaxes, whistling while you work, and communal domestic bliss in a cottage built for men half your height.

I only meant to watch the Heigh-Ho scene for the endwarfins, and then it was two hours later and I'd watched the whole movie.

Endwarfins aren't just a Snow White thing — I get the same hit off the Lollipop Guild in Oz.

endwarfins by Howard Ogden September 13, 2026

Word of the Day on September 14, 2026

caillou

A slang term used to describe a bald person, typically someone who is completely bald or has a closely shaved head. The term is derived from the infamous, hairless kids’ cartoon character of the same name.

Example 1:
“Did you see that caillou over there? His head is reflecting the sun like a disco ball.”
Example 2:
“I think Dave is finally accepting his hair loss. He just went full caillou and shaved the whole thing off.”

caillou by WMH01 September 12, 2026

Word of the Day on September 13, 2026

Brought-upsy

scruples; to have manners;

May also be spelt Brought-upsie

WestIndian/Caribbean in orient - Barbados, WHUT.

Example 1: Child, you ain't got no brought-upsy?

Translation: My Child, have you not any manners?

Example 2: What, you ain't got no brought-upsy?

Translation: I can't believe you're doing that. Were you not taught any manners as a child?

Brought-upsy by B-Town Gilly April 20, 2005

Word of the Day on September 12, 2026