Yes, there is a problem. We are called upon not to celebrate the holidays of other faiths. This is for several reasons. First, of course, we should not engage in foreign, forbidden worship. (Think about the second of the Ten Commandments: “Thou shalt have no other gods before Me.”) Celebrating a holiday can constitute a form of worship. Second, even if our celebrations don’t constitute worshipping false gods, we should do nothing to suggest that we are doing that. We should do nothing to suggest that other religious traditions – in this case, paganism or Christianity – are somehow “truer” than Judaism, and that we believe in them. (This is the principle of “marit ayin” – refraining from doing something technically permissible because it may raise incorrect but plausible suspicions of improper activity.) Third, even if neither of these concerns is implicated, we should not “imitate the practices of the gentiles.” (See Leviticus 18:1-3) We should celebrate Jewish holidays – not those of the other peoples among whom we live. We should seek to be thoroughly at home in the Jewish tradition, and within Jewish culture – and not find our spiritual homes elsewhere.
Having said all that, is it really that problematic to go trick or treating, or to send a Valentine’s Day card to your sweetheart? Isn’t it possible that, as your question implies, our society has in fact created a new category of secular holidays? If no one today “remembers” the pagan or religious origins of these holidays, if those origins have nothing to do with the reasons that people are drawn today to celebrate them, are the concerns raised above still relevant?
That’s a good question! My own response may sound equivocal: it depends. Theoretically, it is problematic to go trick-or-treating, or to send a Valentine’s Day card to a sweetheart. But when my kids were young and Halloween came around, I found trick-or-treating to be a wonderful community-building experience for the family and the neighborhood. I found the notion that somehow I was honoring paganism absurd. Similarly, although I am not at all attracted by the historical background of St. Valentine’s Day, it has occurred to me on more than one occasion to bring my wife flowers on that day. These practices, it seems to me, have evolved far beyond their origins. “Observing” them no longer symbolizes what it once did.
As Mordecai Kaplan once wrote, American Jews live with one foot in American culture and one foot in Jewish culture. So long as that Jewish foot is firmly anchored, I wouldn’t be too worried about Jews partaking in these rather benign secular experiences.