American Idioms – Idiom Wizard Lists Over 5,500 Idioms & Slang Descriptions

Square peg in a round hole


Awkward situation. Impossible dilemma. A square peg (block) does not fit inside a round hole of the same width, so this phrase explains why some things just will not work, regardless of how hard you try to make them meld. (Compare to Like nailing jell-O to the wall or Boil the ocean.)

“He’s not a good salesman because he has an introverted personality, so it is akin to  putting a square peg in a round hole.”

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