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Secret Santa is a form of communal gift giving, that I have seen being done at workplaces to foster closer ties to employees. It is generally done near the end of the secular year. While the wiki article says that it's often voluntary, everytime I've seen them, the voluntary nature of it was not very clear, and it felt pretty obligatory to me.

While one can't give a gift to a non-Jew 3 days before their holiday, how does that halacha apply to this situation? Also what other relevant halachot are there? Does it matter if the instigator of Secret Santa is Jewish? Does it matter if there are other Jews in the group besides yourself?

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At an office I once worked at they called it Mystery Maccabee along the same lines... (where quite a few of the workers were not jewish) –  Naftali Dec 14 '11 at 15:49
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What Halacha says that"one can't give a gift to a non-Jew 3 days before their holiday"? Would this apply to the question about Giving gifts to non-Jewish teachers and bosses? –  morah hochman Dec 14 '11 at 16:01
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As answered in that related question, Avoda Zarah page 2a. is the halacha that says you can't give a gift to a non-Jew 3 days before their holiday. –  avi Dec 14 '11 at 16:39
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@avi: per Shulchan Aruch, Yoreh De'ah 148:4, the three-day thing applies only in Eretz Yisrael; elsewhere, it's prohibited only on the holiday itself. –  Alex Dec 14 '11 at 17:17
    
@Alex good thing I live in Israel :P –  avi Dec 14 '11 at 19:40

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A lot of leniencies have been given over the years, with the goal of not causing ill-will among non-Jewish co-workers, and improving work relationships. (It's quite amazing how many of the prohibitions in the first chapter of Avoda Zara are circumvented in one way or another by the Tosafists, which led one thinker to pen a monograph entitled "Was Rabbeinu Tam a Reform Rabbi?").

In an OU talk several years ago regarding various workplace issues, Rabbi Herschel Schachter insisted that saying "Season's Greetings" to a non-Jewish co-worker was permissible (or certainly "Happy New Year", I presume), but not "Merry Christmas."

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I thought the classic "Reform Tosafot" was about clapping on Shabbat, or something like that. –  Isaac Moses Dec 14 '11 at 16:47

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