Peg and hole puzzle: Solution
Which gives a tighter fit: a square peg in a round hole or a round peg in a square hole? (The tighter fit is the one for which the ratio of peg area to hole area is greater.)
Solution
Consider the following picture:
Suppose that the side length of the large square is
so its area is
Then the circle has radius
so its area is
By Pythagoras’ theorem the small square has side length
so it’s got area
The square peg in round hole fit is given by the ratio of the area of the small square to the area of the circle, which is
The round peg in square hole fit is given by the ratio of the area of the circle to the area of the large square, which is
Since
we have
so
Dividing by 4 gives
so the round peg in a square hole gives the better fit.
This puzzle was contributed by Colm Mulcahy, Associate Professor of Mathematics at Spelman College in Atlanta, Georgia. Colm's own puzzles have appeared in Math Horizons and in the New York Times. He is a long-time columnist for the Mathematical Association of America and has his own blog. You can follow Colm on Twitter.

Comments
A related problem
A related problem which is fun, is to design a peg which fits into a triangular hole, a square hole, and a circular hole leaving no gaps.
Tim Davis
Pressure solution
Couldn't you also consider this problem from the direction of a pressure fit?
In this case, if the height of each peg is the same then the "pressure fit" is equal for both the rectangular prism and the cylindrical hole described above.
A peg is a cylinder with a height, h. The peg would contact the sides of the square hole at the cylinder's tangents lines of length,h. Pressure = force*area. Pressure =force*(4h*negligible width of each contact line)
A rectangular prism peg with the same height, h would contact a cylindrical hole at it's 4 edges. Again the pressure would be equal. Pressure = force*4h*negligible width of each contact line.
pi/4 > 3/4 > 2/3 > 2/pi
pi/4 > 3/4 > 2/3 > 2/pi