What do you do when your job requires you to promote non-Jewish holidays such as Christmas or Valentines day? Should you sell things that promote these holidays? If say you work for the media should you write on the topic if your boss asks you to?

I’m not sure that non-Jewish holidays are necessarily bad, from a Jewish perspective. While Jews shouldn’t participate in Christmas celebrations because it takes them outside of their own service of God, most Christians today (particularly in the US) likely don’t attach to the holiday any of the religious overtones that made it problematic over the years. In an America that has turned it into a celebration of brotherly love and the search for peace on earth, there’s not a lot there that runs counter to Jewish ideas.

Again, from my Orthodox perspective, the fact that non-Jews are doing something that seems good to me doesn’t necessarily mean I should join in. In the case of a holiday that has a history of being a time of pogroms and persecutions, as well as of religious views that contradict mine, there are many reasons a Jew cannot celebrate the day. That doesn’t mean there’s a problem in marketing it to non-Jews, who have few of those issues.

Ditto with Valentine’s Day. It may once have been about worshipping or celebrating a saint, and therefore might have had idolatrous elements (in which case, you probably shouldn’t encourage others to be involved in it, since we don’t want non-Jews engaging in idolatry any more than Jews). But today, it’s more about love in general, spousal love in particular, and there’s little wrong with that.

So unless there’s more to your role than I can tell, or you worry that you will necessarily be bringing more Jews to the holiday than non-Jews, I think you can do your job with a clear conscience.