square peg in a round hole

Commonly associated with a shape sorter, a baby toy that consists of (often wooden) pegs that need to be inserted through holes in a box, using the hole that has the same shape as the peg. While all the shapes are of roughly equal size, each peg will only fit in the hole that has the same shape. Inserting a peg in a different hole would require either modifying or breaking the toy.

• (Received Pronunciation) IPA^(key): /skwɛə ˌpɛɡ ɪn‿ə ɹaʊnd ˈhəʊl/, /skwɛː-/
• (General American) IPA^(key): /skwɛəɹ ˌpɛɡ ɪn‿ə ɹaʊnd ˈhoʊl/

• Audio (General Australian):

  (file)

• Rhymes: -əʊl

square peg in a round hole (plural square pegs in round holes)

1. (idiomatic) 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.

   Synonym: like a fish out of water

   • [1873, [Edward Bulwer-Lytton], chapter XXI, in Kenelm Chillingly: His Adventures and Opinions […], 2nd edition, volume I, Edinburgh; London: William Blackwood and Sons, →OCLC, book II, page 352:

     ["]Now, your son's case is really your case—you see it through the medium of your likings and dislikings—and insist upon forcing a square peg into a round hole, because in a round hole you, being a round peg, feel tight and comfortable. Now I call that irrational." / "I don't see why my son has any right to fancy himself a square peg," said the farmer, doggedly, "when his father, and his grandfather, and his great-grandfather, have been round pegs; and it is agin' nature for any creature not to take after its own kind.["]]

   • 1919, W[illiam] Somerset Maugham, chapter LIV, in The Moon and Sixpence, [New York, N.Y.]: Grosset & Dunlap Publishers […], →OCLC, page 282:

     To these people, native and European, he was a queer fish, but they were used to queer fish, and they took him for granted; […] In England and France he was the square peg in the round hole, but here the holes were any sort of shape, and no sort of peg was quite amiss.

   • [1985 July 9, Eugene Gressman, witness, “Statement of a Panel, including: Elliot H. Levitas, Esq., Kilpatrick & Cody, Washington, DC; Stuart E. Eizenstat, Esq., Powell, Goldstein, Frazer & Murphy, Washington, DC; Stan M. Brand, Esq., Brand & Lowell, Washington, DC; and Eugene Gressman, Professor of Constitutional Law, School of Law, University of North Carolina, Chapel Hill”, in Rulemaking Procedures Reform Act of 1985: Hearing before the Subcommittee on Administrative Practice and Procedure of the Committee on the Judiciary, United States Senate, Ninety-ninth Congress, First Session on S. 1145: A Bill to Increase the Accountability of, Policy Coordination by, and Management of Priorities by Agencies through an Improved Mechanism for Congressional Oversight of the Rules of Agencies […] (Serial J-99-38), Washington, D.C.: U.S. Government Printing Office, →OCLC, page 77:

     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.]

   • [2005, Gini Graham Scott, “Dealing with Danger”, in A Survival Guide for Working with Bad Bosses: Dealing with Bullies, Idiots, Back-stabbers, and Other Managers from Hell, New York, N.Y.: AMACOM, American Management Association, →ISBN, part V (Ethical Challenges), page 153:

     As they say, you can't fit a square peg in a round hole. If your boss is like that round hole and you are that square peg, you aren't going to fit in unless you re-shape your edges. If you can't do that, then look for that square hole where you will fit.]

• square the circle (semantic overlap regarding a difficult problem)