It seems that there isn't a clear answer for how Valentine's Day came about, but we all think it has something to do with romance and expressing love to your significant other. And maybe a nearly naked child flying around shooting at people with arrows.
Valentine's Day is an abbreviation of St Valentine's Day. St Valentine seems to be the center of all this, but nobody's absolutely sure why. And there are many saints who went by that name(I think 14 altogether) so we don't know which one to give credit to for this occasion. Also, what exactly happened on February the 14th??? Some say a feast was held that day, some say it's the day he died, naturally or by execution, some say it's the day he started the letter-writing tradition. Who knows?
The famous legend about him, which probably linked the concept of romance to this special day, says that in prison, on the day he was to be executed(want to guess the date?), he wrote the first ever love letter, supposedly to the daughter of a jail guard there, because she accompanied him in jail and kept his spirits up.
Then who is Cupid exactly? Cupid wasn't originally as cute and lovely as he is pictured today, but more like a mischievous god who happened to be the son of Venus. Unlike now, he liked to deliberately mismatch people and then watch the fun. One story goes that Cupid was sent by Venus to punish a woman called Psyche, but he instead fell in love with her. Psyche's jealous sisters tricked her into thinking he has evil intentions, and she tried to sneak up to him with a knife, but was caught, forcing Cupid to punish her by leaving her. (Another version goes that Psyche was forbidden to look at Cupid, but she violated that law by sneaking up on him)
Then Psyche realized her foolish behavior, and decided to go up to Venus herself to get Cupid back. Venus happily set her many tasks to complete to test her worth, but luckily Psyche managed them all with some assistance from other gods. However for the final task, Psyche was instructed to bring a box into the underworld, take some of the beauty of Proserpine(wife of Pluto the god of the underworld) and put it in the box. She was warned not to open the box, but temptation drove her to do otherwise, and she found deadly slumber inside.
Cupid discovered her in deep sleep, and put the deadly slumber back into the box. He also forgave Psyche for her foolish act. The gods and goddesses, including Venus, were touched by their love and made Psyche a goddess.
So that's the story of the two mysterious figures. Have to cut this really short because I'm racing against time to finish this. So Happy Valentine's Day everyone!!! :D :D :D