riddle (n.) Look up riddle at Dictionary.com
"A word game or joke, comprising a question or statement couched in deliberately puzzling terms, propounded for solving by the hearer/reader using clues embedded within that wording" [Oxford Dictionary of English Folklore], Old English rædels "opinion, riddle, counsel, conjecture," from Proto-Germanic *rædislijan (cf. Old Saxon radisli, Middle Dutch raetsel, Dutch raadsel, Old High German radisle, German Rätsel "riddle"). Related to Old English rædan "to advise, counsel, read, guess" (see read (v.)).
riddle (v.) Look up riddle at Dictionary.com
"perforate with many holes," 1817 (implied in riddled), earlier "sift" (early 13c.), from Middle English ridelle "coarse sieve," from late Old English hriddel "sieve," altered by dissimilation from Old English hridder "sieve," from Proto-Germanic *khridan (cf. German Reiter), from *khrid- "shake" (cf. Old Norse hreinn, Old High German hreini, Gothic hrains "clean, pure"); probably from same PIE root as Latin cribrum "sieve, riddle," Greek krinein "to separate, distinguish, decide" (see crisis).