When I was in grade school, Valentine's Day was one of my favorite holidays.

There were
cards. There was the possibility that your crush actually liked you back. And, there was the
chocolate -- so much chocolate.

Little did I know that the roots of this holiday bore little-to-no resemblance to my childhood
experience of it? We were never taught that Valentine's Day actually originated with an
arguably gruesome ancient festival, where there was no chocolate or exchange of cute, red-
and-pink cards. But love it or hate it, those are the types of things we associate with the
holiday today. After all, there's a reason roughly 114 million Valentine's Day cards are
exchanged each year -- it's what's become expected of us.
So how the heck did we get from an ancient Roman festival to a holiday that compels many
of us to spend no less than $147 on celebrating it? That story, it turns out, is thousands of
years old -- but we'll try to condense it.
How Valentine's Day Began and Evolved
Ancient Rome

Source: Christie's
The roots of Valentine's Day are cited by some sources to lie in the ancient Roman
festival Lupercalia, largely because it took place annually on February 15 -- the day after what is
today the observed date of Valentine's Day -- and involved some very primitive forms of
courtship and matchmaking. But it was also ancient Rome that saw the famous execution of a
St. Valentine on February 14, around 278 A.D. According to legend, he wrote a letter on the
night before his execution to his jailer's daughter, whom he had befriended, and signed it,
"From Your Valentine."
Over two centuries later, Pope Gelasius ordered that Lupercalia be replaced with the February
14 observation of St. Valentine's Day. That set the tone, some believe, for the day's forthcoming
tradition of exchanging "love messages," perhaps in remembrance of St. Valentine's farewell
letter.
The Romans are also credited with constructing the idea of Cupid -- a god of love often depicted
with arrows that, as the legend goes, inflict love upon those who are hit by them. The Roman
version of Cupid was adapted from Eros, a god of passion and fertility in Greek mythology. It
seems that no one is quite sure when cupid became associated with Valentine's Day, but the
fact that both have origins in ancient Roman culture suggests that there may have been some
very early overlap between the two

Shakespeare (and Chaucer) in Love

 Source: Internet Archive

When NPR's Arnie Seipel set out to explore the history of Valentine's Day, he found that it first
became romanticized by classic authors like William Shakespeare in the late 16th century, and
Geoffrey Chaucer in the 1300s.
Chaucer
Dartmouth English professor Peter Travis cites Chaucer's epic poem The Parliament of Fowls,
which was one of the first literary references to St. Valentine's Day, or "Seynt Valentynes day,"
as Chaucer spelled it. One such mention is made, Travis explains, alongside the line, "Now
welcom somer, with thy sonne sonne, That hast this wintres weders over-shake." In other
words, when we celebrate love in the coldest depths of winter -- in February, for instance -- it's
so heartwarming that it makes summer feel less far away.
Shakespeare
Some literary historians credit Shakespeare for the permeation of love into popular culture with
his composition of "Sonnet 18" -- said to be written between 1593-1601 -- a.k.a., "Shall I
compare thee to a summer's day?" It's unclear when or how this particular work became
associated with Valentine's Day, but like Chaucer, Shakespeare compares love to the seasons.
"While summer days may fade and fall into" colder months, writes Shakespeare analyst Lee
Jamieson, "his love is eternal."
Of course, Saint Valentine's day is alluded to outright in Hamlet -- written between 1599-1601 --
when the character Ophelia recites a song about a young lady's experience with the holiday,
which includes lyrics like, "Tomorrow is Saint Valentine's day," and, "To be your Valentine."
The 17th Century and Beyond

Source: American Antiquarian Society

By the 1700s, it's said that Valentine's Day made its way from Europe to the United States,
which aligns with the establishment of the North American colonies between 1607-1770. It
became traditional, according to HISTORY.com, "for friends and lovers of all social classes to
exchange small tokens of affection or handwritten notes." That was more common in England,
however, where the Industrial Revolution began earlier and eventually included the production
of "fancy valentines were extremely expensive to import."

It's said that one American woman, Esther Howland, was so intrigued when she received her
first English valentine wishes greeting in 1847, that she became infatuated with the idea of
manufacturing them in the U.S. She was an early entrepreneur, and instinctively believed that
there could be an American market for these formal, English-style greetings. After procuring
materials like high-quality paper and lace from her father, a stationer, she created what many
credit as the earliest American Valentine's Day greeting cards.

Today, Howland is still honored with the nickname "Mother of the American Valentine," with
many citing her work as the start of a multi-million-dollar industry. But it didn't happen
overnight -- let's take a look at how her work paved the way.