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Rather confusingly, there were more than one Christian martyr named Valentine. Indeed, there are actually two Saint Valentine’s that are celebrated on February 14th, Valentine of Rome and Valentine of Terni. One of them (old records are not specific) was buried on February 14th, thus connecting this date to the name Valentine.
You might be wondering, what exactly does the death and burial of a Christian martyr have to do with romantic love? As with so many holidays, this particular date ended up being conflated with an older, pagan celebration. The date and concept were kept, but the “star” of the show was not a Christian Saint, not the pagan Juno.
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The festival of Juno, Lupercalia, was celebrated on February 13–15th, so the “happy” coincidence of Valentine’s burial cemented the day's new name. The original celebration focused on love and fertility, so it was perhaps difficult to remove this association even if you were, nominally, celebrating a martyr.
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Modern readers aren’t the only ones to notice this discrepancy. February 14th as we know it, only really took off in the 14th century, with Chaucer's poems about it. Two specific pieces, Parlement of Foules and Complaint of Man seem to have sparked off the whole craze, although scholars have noted that the traditions and conventions he writes about don’t seem to have had any basis in reality.
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In other words, this entire tradition might be the figment of the imagination of a poet looking back at the older meanings of Valentine’s Day. So if you rank among the folks who had a big Valentine’s Day fail or you don’t like the holiday in general, perhaps it can help to recognize that the whole idea might be made up in the first place.
Another common and perhaps warranted criticism of Valentine’s Day might be the over-commercialization of the entire thing. In the US alone, 190 million Valentine’s cards are sent every single year. Unfortunately, we do not have an average success rate on these, but one suspects the number isn’t high.
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