Square Peg Into A Round Hole Meaning
(Can we clean up(+) this sense?) (idiomatic) Something or someone that does not fit well or at all; something that will not succeed as attempted, except possibly with much force and effort.
Example: 1873, Edward L. Bulwer, Lord Lytton, Kenelm Chillingly: his adventures and opinions : a novel, page 155:
... 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.
1985, United States Senate, Committee on the Judiciary, Subcommittee on Administrative Practice and Procedure, Rulemaking Procedures Reform Act of 1985: hearing before the Subcommittee on Administrative Practice and Procedure, page 77:
... 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.