The most distinctive feature of conundrum is the deliberate misinterpretation in the course of its application. The present paper attempts a new cognitive approach to the understanding of conundrums. Based on psychological laws of mankind, the conundrum begins with the questioner’s leaving a certain linguistic item on purpose, which will definitely cause deliberate misinterpretation. The process of its understanding is the result of the replier’s taking advantage of the impartment and inheritance of the connotation and denotation to disguisedly replace another concept.