Valentine’s Day: A Little Love, A Little Legend

Valentine's Day might be all pink hearts and candy aisles now, but it didn’t exactly start that way. The history is a tangled mix of ancient Roman festivals, medieval matchmaking, and a fair amount of creative storytelling.

The holiday’s roots stretch back to a Roman festival called Lupercalia—a not-so-sweet event involving animal sacrifices and matchmaking by lottery. (Romance, right?) As Christianity spread, the church rebranded the celebration around St. Valentine, a figure who, depending on which legend you believe, either secretly married couples against an emperor's wishes or simply refused to renounce his faith—and was executed for it.

But it wasn’t until the Middle Ages that February 14th became associated with romance—largely thanks to a certain English poet.

Whether by tradition or poetic license, Chaucer helped spark the idea that February 14th was a day for finding love—just as the birds were said to be choosing their mates as springtime stirred the earth awake.

Cupid: The Original Matchmaker

No Valentine’s Day would be complete without a nod to Cupid—the mischievous little archer responsible for more than a few broken hearts and bashful crushes.

Originally known in Roman mythology as the son of Venus, Cupid wielded a bow and a quiver of magical arrows:

His Greek counterpart, Eros, was imagined as a handsome young man—but somewhere along the line, Cupid transformed into the chubby-cheeked cherub we recognize today. By the Victorian era, artists firmly cemented Cupid’s image into Valentine’s Day—fluttering above lovers and meddling happily in human affairs.

Cupid’s Victorian makeover: sweet, cherubic—and a little mischievous.

Victorian England: Lace, Love, and a Few Surprises

As time fluttered forward, Victorian England took Valentine’s Day to the next level. Handmade cards became works of art—ornate creations adorned with lace, silk flowers, ribbons, and sentimental poetry. Shops even began selling ready-made Valentines for the first time, making it easier (and sometimes more socially expected) to send a little love through the post.

Victorian ingenuity: a “Barometer of Love” card with a tiny movable dial—measuring affection from Esteem all the way to Enrapture, Unity & Bliss.

But not every Valentine was all lace and longing. The Victorians had a playful side—and sometimes, a mischievous one. Hidden messages, clever designs, and even a few tongue-in-cheek surprises found their way into the day’s festivities.

One of the more notorious traditions? The so-called "Vinegar Valentines"—cheaply printed cards filled with biting humor, sarcastic jabs, and warnings about wayward sweethearts. Thanks to the anonymous magic of the Victorian post, senders could mail these little stingers without signing their names—leaving the unlucky recipient to foot the postage bill for a less-than-flattering surprise!

"Here's a pretty cool reception,
At least you'll say there's no deception,
It says as plain as it can say,
Old fellow you'd best stop away."

Victorian poetry at its finest—delivering a splash of honesty, one vinegar Valentine at a time.

And of course, not every sly Valentine relied on biting words alone. Some, like this cheeky "snake in the grass," let the imagery do the talking—delivering a warning that even Cupid’s arrows could sometimes miss their mark.

A slithery Victorian Valentine 'Beware of the Snake in the Grass'—proving that not all hearts came sugar-coated (and yes, that's a snake in fishnets).

Thankfully, most of these sharper traditions faded over time, leaving behind the sweeter spirit we know today. But during the height of Victorian Valentine’s Day fever, things were just ramping up.

By the mid-1800s, the British postal system was flooded with cards—so many that extra deliveries were needed just to keep up. Love, it seemed, traveled swiftly... especially when postage was only a penny.

So if you’ve ever agonized over which card aisle poem feels less awkward, you can thank Victorian England for starting the tradition—where a Valentine could be sweet as lace, sharp as a quip, or somewhere perfectly in between.

How Valentine's Day Became a Big Deal

By the early 1800s, Americans were exchanging handmade Valentines too—but it was a woman named Esther A. Howland who helped launch Valentine's Day into a full-fledged industry. In the 1840s, she began selling the first mass-produced Valentines in the United States, earning her the title "Mother of the Valentine." Her elaborate creations, decorated with lace, ribbons, and colorful illustrations called "scrap," turned simple notes into something truly special—and helped cement Valentine's Day as the card-giving tradition we know today.

Esther A. Howland—the "Mother of the Valentine"—and a glimpse of her beautifully crafted creations.

Today, an estimated one billion Valentine's Day cards are sent each year, making it the second-largest card-sending holiday after Christmas. (Christmas cards clock in around 2.6 billion!) And if you’re wondering who's doing most of the shopping—statistics say women purchase about 85% of all valentines.

Valentine's Day Around the World

While the U.S. has cornered the market on candy hearts and giant teddy bears, Valentine's Day traditions pop up in plenty of places around the globe—and in most countries, it’s still celebrated on February 14th.

Turns out, Cupid’s arrows have quite a reach—and Valentine’s Day has become a truly global celebration.

A Few Valentines of My Own

Growing up, I took Valentine’s Day very seriously. While some kids were tossing together cards the night before, I was planning for weeks. Every note had to be handwritten. Every candy carefully chosen. It was a full-scale production—from glittery stickers to perfectly selected heart-shaped treats.

Fast forward a few years (and a few kids of my own), and let’s just say—not everyone shared my Valentine enthusiasm. My three oldest enjoyed the day, sure, but they were more in the "grab a box of cards from the store" camp. Cute, but not quite the same level of obsessive planning.

And then came my youngest—my Mini-Me in every way.

Me and my Mini-Me at a certain sold-out concert. (Swifties, we see you.)

Valentine’s Day? She lived for it. Every invitation was handwritten. Every card was custom. We’d pack little clear cellophane bags with treats, seal them with ribbons, and she would’ve handed out Costco-sized candy bundles if she could’ve. Watching her light up the same way I did was one of those sweet little reminders that some things really do run in the family—especially a love for over-the-top Valentine’s celebrations.

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Maybe that's what Valentine's Day is really about after all. Not the grand gestures or the glitter (although let's be honest—those help), but the simple joy of making someone else feel remembered, appreciated, and just a little extra loved.

We’d love to hear your favorite Valentine memories—or just say hello! After all, sharing a little love is what the day’s all about. Leave a comment below and help us celebrate the heart behind the holiday.

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