The paper deals with the results of studying contemporary crosswords from the cognitive linguistic standpoint. The author focuses on the following aspects: (i) the crossword as a product of wit and as a specific model of interaction between the author and the reader/ solver; preliminary evaluation of genre-specific and stylistic peculiarities of the riddle as a language game; (2) the crossword as a way of familiarizing the solver with problems pertaining to language faculty per se (lexical polysemy; polynominalization; ellipsis in adjectival constructions, etc.); (3) semantic shifts caused by figurative logic; occasional metaphorical models combined with idioms’ “cryptography” and other devices that are both disorienting and prompting the solver. One can prove that the contemporary crossword is a guide to speech culture by the following: the words being unriddled in a crossword are not interpreted but rather hinted at by means of identifying characteristics taken arbitrarily. The object of “interpretation” modifies its status freely, as the crossword compiler either means the extralinguistic fragment of reality (i.e. the signified), or focuses on the very means of denotation. The crossword uses idioms of varying syntactic structure and style, including (a) aphorisms and (b) restricted collocations (viz. clichéd expressions that do not serve as definitive and general assertions). The solver is supposed to reconstruct and recognize the implied idiomatic context comprising the desired word. The constituents of implicit clichéd word-groups are creatively rephrased by means of arbitrary analogy. The feature used for association with the desired word can be guessed by means of a familiar idiom or cliché hinting at the right answer, as well as by a key word that serves as a specific cultural sign identifying a custom, a popular belief or a piece of country lore. Solving a crossword is not unlike voluntarily passing a self-examination, with the reader/solver getting an opportunity of evaluating their education (as s member of a community) and their intuition (as a native speaker).