Would it be possible to add humor based flagged questions that are not serious in nature, not quite open threads, but would be variations on a theme, just to get the crowd sourcing response. Something like "Did Hillary just get schlonged by Weiner?"

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No, because this would contradict the very nature of StackExchange.

We are here to learn. To learn from facts, not from someone's sharp tongue and a quick wit.
There are plenty of political-related chat boards and forums around, and humorous posts here would only dilute the valuable information.

Exceptioุุุุ้้้ns from this rule are very rare. :-)

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The closest thing I know of on a Stack Exchange site is Mi Yodeya (Judaism) and their Purim Torah policy. As part of a cultural tradition, they have a few weeks out of the year where they can ask humorous questions, but only with strict guidelines about the nature of the humor (e.g. a misinterpretation of the Torah).

If we allow political humor, I think we would also have to set guidelines as to what kinds of humor is allowed (we don't want rude or offensive humor. I also think it would be a difficult to moderate.

Additionally, we don't want to change the goal of the site. Mi Yodeya is primarily a site about serious questions, so Purim Torah questions must be closed at the end of the allowed period. I think that this site is about serious questions, so we don't want to encourage it to become a humor site.

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    sigh. A 1-word answer with zero argumentation on Meta gets 4 upvotes (whether it's because it's by a moderator, or because people dislike the question, or questioner, or a combination thereof). Everything that's wrong with SE, in one short example. It doesn't matter if you agree with the answer, a 1-word answer shouldn't be upvoted. – user4012 Nov 4 '16 at 15:29

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