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A convert is required to honor his parents. This does not apply when fulfilling their requests violates halacha. I suspect that many parents of converts, who are not knowledgable in halacha and probably don't care to be, would not really understand or accept a halachic response.

In the case of Christian or nominally-Christian parents, there can be tensions in late December. Whether Christianity is avodah zarah is controversial. One seemingly-non-religious aspect of their holiday is giving gifts, which is typically done at family gatherings (not privately). Leniencies appear to exist in the workplace, so one might say "if so, how much the moreso for parents?". While we are not supposed to give gentiles gifts before their holiday, it has been argued that we aren't necessarily concerned about prompting their worship by giving gifts (they don't tend to see the gifts as religious). On the other hand, and as noted there, there is also the consideration of imitating the ways of non-Jews.

Most of the converts I know are stumped at this time of year. Strict halacha seems to say they shouldn't participate in these family gift exchanges, but refusing to do so can cause upset (concerns of shalom bayit). In some families deferring to a different time of year (e.g. Purim, or emphasizing birthdays instead) is not acceptable to the parents.

So my question is: beyond consulting his rabbi (which he should of course do, though the rabbi probably doesn't know the family members), how should a convert weigh these various factors? How should he decide when to say "sorry it upsets you Mom, but no" versus going along with it? I am looking for practical answers moreso than halachic explanations.

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I don't know if this counts as different times of year, but deflecting to Thanksgiving or New Years might be a better option (assuming issues surrounding celebrating those holidays can be dealt with). –  Double AA Dec 20 '12 at 4:25
    
If [strict] Halakhah says not to participate in these family gift exchanges, what is there to weigh? Why not decline with respect( like with other things they'd have to refuse)? As an aside: I would have thought that problems concerning interacting with non-Jewish friends and family should have been made clear to perspective converts( and resolved?) before they converted( so that they don't become "stumped at this time of year"). –  Tamir Evan Dec 20 '12 at 9:32
    
@TamirEvan, because the strictest chumra doesn't automatically apply in a system that supports both strict and lenient interpretations. Also, "seems"; the areas mentioned here are controversial. Rabbis do discuss these issues with prospective converts, but apparently it's not possible to fully prepare for these situations in advance (and sometimes people, particularly aging parents, change over time). –  Monica Cellio Dec 20 '12 at 14:02
    
@MonicaCellio If it's just a Chumrah , then the convert can do whatever( within Halakha ) they choose, and the better course of action would be to follow the Chumrah ( if they accept it's validity). But if it is Halakhah , strict or otherwise, then it is to be observed. If there is controversy or doubt over what is obligatory, what is a Chumrah , and what is allowed, I see little recourse but to ask a Halakhic expert( a Rabbi), who's authority you accept, about it. –  Tamir Evan Dec 20 '12 at 17:49
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You might be able to preempt the whole thing by linking the gifts to Channukah. Both requesting that you receive gifts only then, and giving them then. (This will be easier when Channukah comes first, so maybe wait for a year when that happens, and then make it a known thing for future years.)

In my local school they suggest giving annual gifts to teachers on Purim instead of Channukah, to avoid it looking like non-Jewish holiday gifts.

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Does doing this help to promote Chanukah as "Jewish Christmas" (already a problem in the US at least)? And if so, how strong a concern is that? –  Monica Cellio Dec 19 '12 at 13:54
    
@MonicaCellio It certainly doesn't help, but it's better than nothing - especially if there are going to be hurt feelings. However, that's why I suggested the Purim option. –  Ariel Dec 19 '12 at 21:36
    
Good point about Purim. In one case (at least) deflecting away from December ("let's make a bigger deal about birthdays instead") didn't work, so Purim wouldn't work there either, but it could work well in other cases. Definitely better than Chanukah if you can swing it. (I've edited the question to reflect this.) –  Monica Cellio Dec 19 '12 at 21:44
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@MonicaCellio I was rather young when this was a real issue for my family (my father ז"ל was a convert), however I do recall that my (non-Jewish) grandmother would specifically send us Chanuka gifts. It all really depends on the personalities involved. For my father's family it apparently wasn't a big deal, especially as they knew that whatever we were doing (or not doing) was purely for religious reasons and had nothing to do with them personally. However, many families aren't as easily able to make such distinctions. –  LazerA Dec 20 '12 at 2:03
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