fit a square peg in a round hole = to do the impossible
to square that circle = to do the impossible
to be square
to come full circle
circle jerk
The term square meal is a nautical term from the days of old sailing ships. Any significant meals (usually the last one of the day) would be eaten off a square-shaped wooden plate, which also served as the tray. A decent meal on board became known as a square meal.
le da mil vueltas
he runs circules around (another person)
how do you square that circle?
triangulate
the pentagon