Literally yes, but in practice the situation where exactly one question (and no more) is allowed is unusual. For this reason, the first would probably not be interpreted as strictly enforcing such a restriction. To emphasise that really only one is allowed you could say "You can ask me any one question".
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teacherJapanYou have a very flexble way of thinking, so you can adjust to any situation/any situations."any situation" feels more natural to me. I suppose you are interested in whether there is any difference between this and the first sentence in respect of singular/plural, and if so, why. One theory might be that situations are considered as separate and se