The Origin & Evolution of Sweetest Day

by Erica G.

October 8, 2021


From a corporate philanthropic marketing event to a Midwestern mini-Valentine’s Day, learn how Sweetest Day started and how it has changed over the years.  Now a special day to remind someone you’re sweet on them, get some ideas for sweet and sexy ways to celebrate on October 21st (edited for 2023)!

Picture yourself in a business meeting 99 years ago, working for a candy company. The bosses are looking at a horrible handwritten balance sheet of their faltering company, heads nervously shaking, voices booming, wondering how they will stay afloat through winter. They know they need to make it back to the booming times like Valentine’s Day, when candy is bought with reckless abandon. Even the cocoa competition is freaking out – scared enough for multiple local confectioners to call a truce and meet to figure something out together. Suddenly, someone stumbles across an idea that just might save everyone in the candy industry. Think of the children!

That’s right! Why not start giving away candy to kids, the underprivileged, and shut-in people? We will produce more chocolate and start charitably giving it away to brighten someone’s day. It will start a public trend! Others will buy chocolate as a sweet gesture for their loved ones or those in need, and sales will come roaring back to life! But what should it be called? You, being the go-getter that you are, raise your hand in this meeting 99 years ago, busting out of your wrinkly suit to let everyone know what the day should be called: Candy for Everyone Day!!!

Minutes later, as you gather your things and put them in a box, then are escorted out of the building that you used to work in, you see the other executives hugging and smiling in the big meeting room, overhearing through the cheers and hurrahs the real chosen name of this new holiday- Sweetest Day. And so the tradition begins…at least in the Midwest.

Sweetest Day may have corporate & commercial roots, but fast-forward 99 years and it’s come a long way. It may not be well-known everywhere, but the knowledge has been spreading beyond the Midwest for years now.  One of the biggest hurdles to awareness may be that it’s a floating holiday, always landing on the 3rd Saturday of October.  Mark your calendar now, because it’s no longer about only candy. There are plenty of sexier ideas that will satisfy more than just your sweet tooth. Here are a few suggestions to help make Sweetest Day fun to celebrate this year and for years to come.

Tasty Looks

Becoming the treat this Sweetest Day is as simple as slipping on a new sexy piece of lingerie. Make mouths water when you wear this Renee Lace & Mesh Babydoll in a bright candy color – slightly see thru, completely irresistible!

Forget that full-body robe for a weekend and instead try out a Romance Me Eyelash Lace Gown. Wearing this isn’t quite as warm as a fuzzy robe, but steamy thoughts will arise in your partner in no time once they see you in this yummy piece.

Want to invoke some sweet but sinister thoughts? How about a Sweetest Day strip tease? Start off wearing your weekend loungewear, but underneath, surprise your lover by wearing a seductive bodystocking. Your body will look incredible, and your confidence will soar!

Sweet Vibes

You are on Intimacy Advisor reading our lusty articles, so I am going to assume you are somewhat familiar with sex toys. But just in case, why not go with a classic tried & true vibe that will help lead to sweeter stimulation, and maybe bigger orgasms! Bullets are discreet and powerful, plus quite popular in a pinch. Basic controls that are easy to operate make them perfect for coupled fun, providing extra stimulation during foreplay or any kind of sex.

Want to simulate penetration? How about a Thrusting Jack Rabbit vibe? This toy not only vibrates and tickles your clitoris with its cute bunny ears, but it also features a realistic thrusting motion in the shaft for extra stimulation (with minimal effort) that will help take your orgasms over the edge.

Sweet Whispers

Sometimes, telling someone “Happy Sweetest Day” just isn’t enough. Why not use your mouth for more than just lip service, and show them how much you care? You’re never too old to learn new tricks, and you just might stumble across new ways to get your partner to climax. Brush up on your oral technique (or maybe give your partner a not-so-subtle hint to that they could use some help) with a book on the fine art of oral sex.

Sexy Snacks

Honor the tradition of Sweetest Day by incorporating a few tasty flavors into your sexy weekend, including chocolate. Let your lover become Bob Ross and create a delicious masterpiece all over your body with this aphrodisiac chocolate body paint from Shunga. Best of all, the artwork created all over your body will be completely edible, so enjoy the creativity, then enjoy the excitement of having the chocolate licked clean wherever it is painted!

Celebrating Sweetest Day is way more fun than other ‘holidays’ that land on the 15th this year (take that, National Dictionary Day)! Use this special day to get in the mood and celebrate with the one you love. It’s the perfect opportunity to get the passion flowing your relationship.

You cannot copy the content of this page