mid-15c., "sweetheart chosen on St. Valentine's Day," from Late Latin Valentinus, the name of two early Italian saints (from Latin valentia "strength, capacity;" see valence). Choosing a sweetheart on this day originated 14c. as a custom in English and French court circles. Meaning "letter or card sent to a sweetheart" first recorded 1824. The romantic association of the day is said to be from it being around the time when birds choose their mates.
For this was on seynt Volantynys day
Whan euery bryd cometh there to chese his make.
[Chaucer, "Parlement of Foules," c. 1381]
Probably the date was the informal first day of spring in whatever French region invented the custom (many surviving medieval calendars reckon the start of spring on the 7th or 22nd of February). No evidence connects it with the Roman Lupercalia (an 18c. theory) or to any romantic or avian quality in either of the saints. The custom of sending special cards or letters on this date flourished in England c. 1840-1870, declined around the turn of the 20th century, and revived 1920s.
To speak of the particular Customs of the English Britons, I shall begin with Valentine's Day, Feb. 14. when young Men and Maidens get their several Names writ down upon Scrolls of Paper rolled up, and lay 'em asunder, the Men drawing the Maidens Names, and these the Mens; upon which, the Men salute their chosen Valentines and present them with Gloves, &c. This Custom (which sometimes introduces a Match) is grounded upon the Instinct of Animals, which about this Time of the Year, feeling a new Heat by the approach of the Sun, begin to couple. ["The Present State of Great Britain and Ireland" London, 1723]