square peg in a round hole UK /skwɛə ˌpɛɡ ɪn‿ə ɹaʊnd ˈhəʊl/US /skwɛəɹ ˌpɛɡ ɪn‿ə ɹaʊnd ˈhoʊl/ noun1 •Someone or something that does not fit well or at all in a certain setting; a misfit; hence, someone or something that will not succeed in an endeavour, except possibly with much effort and force.It is almost as if you have guidelines for putting a square peg into a square hole, but we are trying to apply those same guidelines to put a square peg into a round hole. — 1985 formssquare pegs in round holes