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In a course of philosophy I heard “I mean it’s not like you’re going to fall asleep already, riddle me that”. My dictionary gives me only the noun’s signification “mystery”. but I guess it is used her as a verb. It’s mean something like “make that mysterious”?

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What did the person who said it have to say? –  Matt Эллен Mar 5 at 9:14

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Riddle me that is an idiom that means: Go ahead and try to explain that to me.

It trades upon the secondary meaning of riddle which is to solve or explain a riddle to someone. Link to definition here.

So essentially when someone says "Riddle me that (or this)" they are saying:

I find the statement I just made to be puzzling to the point where I consider it to be a riddle. Go ahead and try to explain it to me.

When someone says that, they typically don't expect an answer to be easily forthcoming.

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I'm not quite sure you can really call it an "idiom". OED sense 3 (for the ponder/puzzle verb, not the sift/separate with a sieve one) has To solve or answer (a riddle, question, etc.). Also: to solve a riddle for (a person). Essentially, it's just an ordinary construction. To me, an idiom is a form whose meaning can't be directly derived just from the literal dictionary definitions of the individual words. –  FumbleFingers Mar 4 at 2:53
    
@FumbleFingers Riddle me this or Riddle me that are idiomatic in the sense that you use them en bloc and in a singular manner that you would rarely use outside of the phrase. You would say solve that for me. I never hear anyone use riddle in this sense otherwise. Hence, I say idiom. Perhaps you'd prefer expression . . . but after our last discussion on this, I've found most dictionaries to give them semantic equivalence. –  David M Mar 4 at 2:58
    
Well, since I have OED open... idiom 3. A form of expression, grammatical construction, phrase, etc., used in a distinctive way in a particular language, dialect, or language variety; spec. a group of words established by usage as having a meaning not deducible from the meanings of the individual words. –  FumbleFingers Mar 4 at 3:02
    
@FumbleFingers I don't deny that it is a known usage. But, it is more obscure in the sense that it is never used outside the expression (making it not as deducible). Hence I've called it an idiom. –  David M Mar 4 at 3:11
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Note: People usually say riddle me this before stating a conundrum or riddle me that after it. –  Bradd Szonye Mar 4 at 3:34

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