Askance, which etymologists believe may have been influenced by askew, comes from Middle English forms such as askaunce, a-skans, a-skaunces, meaning variously "in such a way that," "as if," "as if to say," and "artificially" or "deceptively." The word was first used in English in the 16th century with the meaning "sideways" or "with a sideways glance," and writers over the years have used the suggestion of someone looking askance at something to express a number of feelings from disapproval and distrust to jealousy.