This question comes up every year. Every Reform rabbi I have ever heard speak about it says, "Sure. Why not?"
Valentines Day has become so secular, such a part of the social fabric, it doesn't cause too many shpilkes religiously. Hallmark has far more to do with the holiday than Hashem does. Orthodox Rabbi Benjamin Blech's opinion is that it's fine for Jews to celebrate Valentines Day; we should, in fact, celebrate love every day. Read what he has to say here.
The history of Valentines Day, formerly referred to as St. Valentines Day, goes all the way back to Romulus and Remus. Love, martyrdom, and fertility came together, and the holiday was born. Over the centuries, it grew and changed into the flowers-cards-and-chocolates extravaganza we celebrate today. More about that here.
So, if you're Jewish, or if your sweetheart is, go nuts. Order up special gift of a hand-made papercut, with a mushy message from a sacred Jewish text, lovingly framed and signed by the artist. Make a splash.
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