Valentine's Day stems from the Roman festival "Lupercalia". As most Roman festivals, it was a sensuous affair. Young women would place their names in a box and young men would draw the name out. The man did not need to ask for a date, plan a dinner setting or a movie. Just draw a name and off to fornicate.
One of the most intriguing suggestions for the origin of the heart symbol stems from the seventh century B.C. city-state of Cyrene. Cyrene traded the rare, now extinct, plant silphium. It was known as a means for birth control. The seedpod of the silphium looks exactly like a valentine's heart. Moreover, its use in sex is an obvious connection to love.
However, turn the heart upside down and it becomes a particularly intriguing symbol. Now the heart looks like a pair of plump, dangling breasts. The heart also compares favorably to the female buttocks.