Phrase originally used by the Riddler at the beggining of one of his riddles, asking the listener to explain the riddle. Now used as a challenge to someone to provide an answer to a question that has no apparent answer.
Riddle me this - why did "Batman & Robin" with the collective talent of George Clooney, Chris O Donnell, Uma Thurman, John Glover and even Alicia Silverstone suck so hard?
by Little Green Bag July 04, 2009
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A person whom likes to bull shit about pointless thing to come to no objective
So i hear that jake riddle me this about some bull shit that happen last night at the club.
by the boss aka tupac February 18, 2012
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There isn't even a meaning, It just means please explain.
Riddle me that Ron.
by Cloza69 March 12, 2017
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When a person of weaker mind skills and most of the time their name is Joe blow and he tries to outsmart you in the text world but is merely playing checkers when you're playing chess.
Out riddle me is when Joe Blow tries to text you false outrage and you know that he's playing checkers but you're playing chess
by LOFT AND SHOVE October 05, 2017
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when somene wants to recieve information from a shawtay, when something is being pondered

other variations include : "shwatay, riddle them this"

"shawtay, riddle me this"

to be sung to the tune of t-pain's song "buy you a drank"
SHAWTAY, YEAH EE YEAH YEAH
SHWATAY, RIDDLE ME THAT
1: Yo, why the world gotsta be so messed up and bucket of crackers?
2: Shawtay riddle me that.

also

1: This banana is delicious!
2: Shawtay riddle me that.
by riddlingshawtay December 30, 2009
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A riddle that is so genius and stumping that anyone who encounters it will scream timber at the peak of their orgasm
ohhhh, oh im going to riddle me timbers till my pants are wet
by i dont mind 69 all the time September 25, 2009
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