No, seriously... Valentine's Day, as it's celebrated in the UK, the US, and whatever other countries have decided to pick up on it, was created by retailers in the late nineteenth century to prop up sales during the after-Christmas slump. An obscure saint who was vaguely connected to petitions for romantic love was pulled out of the calendar because sales were terribly grim in February, and from that an obsession was born.
To give them props, though, it is the most successful marketing ploy in the history of modern retail. I mean, there are other commercial holidays, but only Valentine's Day was created by retail and then picked up by the culture; other made-up holidays like Mother's Day and Labor Day were created by people and enacted by government before anyone thought to commercialize them.
But if we're talking about your current relationship, if you take him out on the fifteenth when it's all half-price, you have to buy him twice as much. And then tell him you waited the extra day so you could give him more on a limited budget.
I loathe Valentine's Day, but I truly loathe cheap. And unless your boyfriend is a big bargain-hunter, he probably does, too.