In the days when these holidays where celebrated as religious obsrvances - no question that they were outside the Halachic Pale. This is well-documented in Talmud Avodah Zoro and the corresponding Rambam Hilchot "AKu'M"
Stage 2 - Renouncement
When an idol worshipper renounces his idol, that idol reverts to being profane, secular. It is permitted for most uses - although it may never be used for any holy ritual purpose
Aspect 3 - Hashkafah or "Spirit of the Law"
Even when Halachically permitted, a former idol may carry "spritual baggage" thus - while being technically permitted does not necessrily make it desirable.
No doubt Holidays such as Halloween, Ground Hog Day, Valentine's have morphed into something secular. The questions remain
A How complete are those renouncements? IOW are witches still stirring their cauldrons on Halloween?
B. How much Pagan or non-Jewish overtones remain?
It seems to me that a Valentine's Day card or flowers to one's spouse is fairly innocuous. Maybe passively watching a Mardi Gras parade as entertainment is less offensive to the "spiritual" aspects of the law. OTOH, trick-or-treating dressed as a ghoul or goblen seems to me more sketchy.
At any rate, any participation for the sake of assimilation is questionable and not desirable, even when not outright forbidden.
However, there are some areas where innocent participation may do no harm. It would always be a good idea to Weigh Community Standards and to consult one's Spritiual Leader
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.
We need to be very careful in granting approval in every instance. Whereas we might allow “Trick or Treating” on Halloween or sending a Valentine’s card to a loved one, we need to note that an imprimatur for these might lead someone to feel carte blanche for the Easter Bunny or Saint Nick. Halloween is a pagan ritual associated with All Saints Day in the Church as well as the obvious of Saint Valentine. We should make a distinction between those festivals that are specifically non-Jewish and those in which we can participate as part of our society. The only way to make that distinction is through educating ourselves as to the meaning behind each observance and then choose either to participate or absent. When those observances are specifically Christological, we need to refrain. But when a school teacher helps the 4th graders in creating Valentines cards for Mom or Dad, there should be no problem.
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