Celebrating Your Sweetest (Day), Then & Now

by Kristin T.

October 19, 2024

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From a philanthropic corporate marketing event to a Midwestern Valentine’s Day Lite, learn how Sweetest Day – celebrated this year on October 19th – started, and how it has changed over the years. Now a special day to show appreciation for your sweetie, read on for some sexy gift ideas and ways to celebrate Sweetest Day that will satisfy more than just your sweet tooth.

Happy Sweetest Day, Lovers! If you’re from somewhere in the upper Midwest…like, pretty much the states where Lover’s Lane has stores…you probably know exactly what I’m talking about. If you’ve spent most of your life anywhere else in the world, you might be saying “Happy WHAT??” The third Saturday in October is known to many, at least in this region, to be Sweetest Day. Nowadays, it’s a minor holiday perfect for telling someone you’re sweet on them, giving something sweet or sexy to your lover, or just celebrating all the sweetest people in your life. While the ways we celebrate it have changed, even in the age of the internet, the holiday hasn’t moved too far beyond the state borders of where it started a little over 100 years ago as a charitable day of sugary giving.

So how did Sweetest Day begin? The origins are a bit murky, though most stories tie it back to 1922 and a man named Herbert Birch Kingston, an employee at a candy company in Cleveland, OH. He may have been looking to revive Candy Day, a.k.a. “The Sweetest Day of the Year” – a short-lived holiday started by the local candy companies and sugar producers in 1916, quickly getting the kibosh in 1917 due to sugar rationing during World War I.

Kingston mostly wanted a way to show a spirit of giving and bring happiness to people who were often forgotten. He recruited some fellow candy makers to distribute sweets and small gifts to children in orphanages, the less fortunate, and those who were home-bound. Many other local candy companies joined in on the charitable giving, seeing it as a great way to give back to their communities. They also hoped to encourage the public to do the same, buying more of their candy to give to loved ones and those in need. While things were slowly recovering from the lean times of WWI, the still-struggling candy companies agreed that a holiday encouraging folks who could afford it to buy sweets – still considered a luxury for most people – for giving to others was a pretty brilliant idea.

In the 1930s, many popular movie stars started getting involved in the cause. They bought candy and donated it to the needy as well, including local newspaper boys and young hospital patients in Cleveland. They also popularized the event by posing for magazine & newspaper ads reminding people to buy their sweeties some candy to honor the day. And while greeting cards are popular gifts for Sweetest Day now, we can’t exactly call it a Hallmark holiday – they didn’t get in the game with making special cards for it until the 1970s. This time period, especially, started to mark its transition to a holiday mostly celebrated between romantic couples.

Like many modern holidays, Sweetest Day was perhaps rooted in commercial interests, however well-intentioned. Fast-forward a little more than 100 years, though, and it is now more like a mini Valentine’s Day in the greater Great Lakes region. No longer just about giving candy to those in need, it has become a day to celebrate loved ones – romantic and otherwise – and show your appreciation to those you love through sweet little gifts or words of kindness. While it’s still not well-known everywhere, it has been slowly creeping beyond the Midwest for years. One of the biggest hurdles to sustained awareness may be that it’s a floating holiday, always occurring on the 3rd Saturday of October. Unlike Valentine’s Day which always occurs on February 14th, it may be harder to remember a day that changes what date it falls on every year.

Even if you’re just learning about Sweetest Day for the first time as you read this, it’s not too late to celebrate your sweetie! You can always plan an impromptu special date night, making sure to make a stop at a Lover’s Lane store near you. It’s definitely no longer just about candy, and you can use it as an excuse to spice up the day for your sweetest as much as you’d like. Since we never want you to forget again, here are a few suggestions to help make Sweetest Day worth celebrating this year and for years to come. Remember, Sweetest Day gifts don’t have to be a lot…just make it sweet!

Tasty Looks

Becoming the candy on Sweetest Day is as simple as slipping on a sexy new piece of lingerie. Make mouths water when you wear this Bubblegum Heart Chemise or a Renee Lace & Mesh Babydoll, both in bright candy colors. Slightly see-through, totally irresistible!

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

Want to invoke some sweet but sinister thoughts? How about a Sweetest Day strip tease? Start off wearing your typical weekend loungewear, but underneath, surprise your lover by wearing a seductive bodystocking that leaves little to the imagination. Your body will look incredible, and your confidence (and your lover’s heart rate) will soar! Guys can get in on the fun, too. For anyone who would rather their partner show off his package than receive a package of chocolates, you can’t go wrong with the Envy Snap Down Boxer Brief or the perfectly candy-hued Solid Envy Jock.

Good Vibes

You are on the Intimacy Advisor blog, so I am going to assume you are somewhat familiar with sex toys. Just in case you’re new here, though, why not try a classic vibe that will help lead to sweeter stimulation and bigger orgasms? Bullet vibrators like the Intro to the O Beginner’s Lipstick Bullet or the Spun Sugar Cotton Candy Mini Vibe are discreet and powerful. They slip easily into nightstand drawers and overnight bags. Simple controls and maneuverability make them perfect for coupled fun, providing extra stimulation during foreplay or any kind of partnered sex.

Want to simulate penetration with a side of good vibrations instead? How about The Sonic Rabbit Thrusting vibrator? This toy not only vibrates and tickles your clitoris with its cute whiskers & 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. Any candy-colored dildo also makes a perfect Sweetest Day gift for your sweetie or yourself!

Sweet Whispers

Sometimes, just telling someone “Happy Sweetest Day” doesn’t seem like enough. If you want to use your mouth to show them you care…there are ways! Even if oral is not usually your thing, trying it may unlock incredible new ways to get your partner to climax. Make things tastier and more exciting with some Dick Lips Gummy Cock Rings or BJ Blast Oral Sex Candy…it’s like Pop Rocks for your privates! Brush up on your oral techniques (or maybe give your partner a not-so-subtle hint that they could use some pointers) with a book on the fine art of oral sex. Blow Me Oral Sex gel from CG can also make a mundane BJ smooth, slippery, and sweeter than cotton candy!

Sexy Snacks

Honor the original tradition of Sweetest Day by incorporating a few tasty flavors into your sexy weekend, including chocolate! Nosh on a special dessert to get you in the mood, like the Fantasy Aphrodisiac Chocolate sex enhancement with a libido-boosting version for males and females. Let your lover play Bob Ross and create a delicious masterpiece on your body with this aphrodisiac chocolate body paint from Shunga. Best of all, the artwork created all over your body is completely edible, so enjoy the creativity, then enjoy the excitement of having the chocolate licked clean wherever it is painted!

Whether or not you celebrate Sweetest Day, we like to honor it here at Lover’s Lane as another important reminder to spend some time with your loved ones & remind them how special they are to you. However it started, why not use this special holiday to spark the mood and celebrate with your lover? With plenty of sweet gifts and fashionable fun to go around, it’s the perfect opportunity to get the passion flowing your relationship…sugar high optional.

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