Commercialized, stressful, sad. Lots of folks might describe Valentine's Day using those words, whether they have reason to celebrate with a partner or not. If the day packaged and sold to you in the name of love feels as disingenuous as that U2 song repeats the phrase "in the name of love," you're not crazy -- it is! The actual history of Valentine's Day is a fraught one, filled with murder, abuse, and the failures of romance. Here is the historical horror, in the name of love.
It started with a violently abusive Roman holiday about wolves
The furthest back we've been able to trace the origin of Valentine's Day is a Roman feast day called Lupercalia (from the Latin "lupus" for "wolf"). It was a holiday celebrated in mid-February where, per the Greek writer Plutarch, "many of the noble youths and of the magistrates run up and down through the city naked, for sport and laughter striking those they meet with shaggy thongs." They mirthfully physically abused women who were pregnant or infertile, on the logic that whipping them would help them with the babymaking. Plutarch writes that women of rank were into this and would "purposely get in their way" to receive punishment, and I would believe that bit whole-hog if this were not the same culture that quite literally defined the word "patriarchy." After the dudes were done, they sacrificed two goats and dog and congratulated themselves by anointing each other with their blood.
There's the whole matter of several Valentines dying
That was Lupercalia, but Valentine's Day is named after St. Valentine, the saint canonized by the Roman Catholic Church as a patron of love, young people, and happy marriages. Here's where the history gets murky: several Valentines in the Roman Empire were executed or martyred in the name of Christianity -- at least two of them in the 3rd century by Emperor Claudius II alone, both on February 14. Claudius (also known as Claudius the Cruel) executed the first, Valentine of Rome, for illegally marrying people after the emperor had explicitly stated marriage was not allowed under his Roman reign. The second, Valentine of Terni, was a spiritual leader and faith healer said to have restored sight to the blind. A third was also believed to have been martyred in Africa.
At some point in the next two hundred years, after the Roman Catholic Church gained more of a foothold in Rome and on the continent, Pope Gelasius I took steps "to purify" the month of February. Following an 1,800-page letter to the Roman senator Andromachus, he successfully abolished Lupercalia in the late 5th century and replaced it with St. Valentine's Day. Rome even keeps a skull of the St. Valentine of Rome on display that tourists with morbid curiosity can check out for free.