conundrum [L16th] The origin of conundrum is itself a conundrum. In 1596 the English political writer Thomas Nashe (1567–1601), who loved extravagant words, used it as a term of abuse for a crank or pedant: ‘So will I … drive him to confess himself a Conundrum, who now thinks he hath learning enough to prove the salvation of Lucifer.’ The word later came to refer both to a whim and a pun. The current sense of ‘a riddle or puzzle’ dates from the late 17th century.