<P> Square is slang for a person who is conventional and old - fashioned . This sense of the word "square" originated with the American jazz community in the 1940s, in reference to people out of touch with musical trends . Older senses of the term square referring positively to someone or something honest and upstanding date back to the 16th century . </P> <P> The English word square dates to the 13th century and derives from the Old French esquire . By the 1570s, it was in use in reference to someone or something honest or fair . This positive sense is preserved in phrases such as "fair and square", meaning something done in an honest and straightforward manner, and "square deal", meaning an outcome equitable to all sides . </P>

Where does be there or be square come from