The gift-giving business on Valentine’s Day is a serious one. In the US alone, people are expected to spend a record $29.1 billion on the holiday in 2026, according to the National Retail Federation’s annual survey. That total covers presents for partners, family, friends, coworkers, teachers, and even kids’ classmates—basically anyone who could use a little love.
Whether it’s dinner, chocolates, roses, or a funny gift like the ones on this list, it all looks pretty sweet on the surface. But the tradition has a long backstory—and it isn’t exactly romantic or adorable.
Valentine’s Day’s origins are famously murky, and historians still debate where the modern holiday really begins. Still, one common starting point is Lupercalia, an ancient Roman fertility festival celebrated every year in mid-February.
It was held to honor Faunus, the Roman god of agriculture, as well as the legendary founders of Rome, Romulus and Remus, and it was about as far from romance as you can imagine.
The celebrations involved animal sacrifices, drunken revelry, and a lottery system that paired men and women together in matches that often led to marriage. Not exactly the candlelit dinner we picture today.
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But how did a rowdy pagan festival eventually become the holiday of love? The bridge, at least in part, appears to be Christianity.
In the third century, there were several Christian martyrs named Valentine who were executed on February 14, though it is not entirely clear which one of them history eventually latched onto.
The most popular legend tells the story of a priest named Valentine who secretly performed marriages for young Roman soldiers after Emperor Claudius II banned the practice, believing that single men made stronger fighters.
Valentine was eventually imprisoned for his defiance, and before his passing, he allegedly wrote a letter to his jailer’s daughter—who was blind, and whom he had miraculously restored sight to—signed “From your Valentine,” an expression that lives on to this day.
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As the Roman Empire gradually shifted toward Christianity, Lupercalia began losing its footing. At the end of the 5th century, Pope Gelasius I officially forbade the celebration, and many credit him with replacing it with a Christian feast day in honor of St. Valentine—part of a broader effort by the early Church to absorb and reframe popular pagan traditions.
Not everyone agrees on that link, though. Some historians argue there is little solid evidence that the two were ever directly connected, and that the story of one neatly replacing the other is more legend than documented fact.
What is clear is that over time, as the Empire became less pagan, the mid-February festivities slowly moved away from Roman gods and toward St. Valentine instead.
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Even then, the holiday still had very little to do with love. That connection would not come for nearly another thousand years. It was the poet Geoffrey Chaucer who is widely credited with first linking Valentine’s Day to romance, in his 1375 poem The Parlement of Foules, partly because February falls around the time European birds begin mating.
Later poets, including Shakespeare, followed Chaucer’s lead and helped cement the romantic associations we know today.
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From there, the holiday grew steadily sweeter. The first known written Valentine was a poem composed in 1415 by Charles, Duke of Orleans, written to his wife while he was imprisoned in the Tower of London.
Handmade cards became popular through the Middle Ages, and by the mid-18th century it had become common for friends and lovers of all social classes to exchange small tokens of affection or handwritten notes. By the year 1900, printed cards—many depicting the arrow-launching cherub known as Cupid—began to replace written letters as printing technology improved, thanks to a company that would later become Hallmark.
Today, that same company estimates that 145 million Valentine’s Day cards are sent each year, making Valentine’s Day second only to Christmas in terms of card-sending holidays.
