Two People, One Hour, and Seven Chances in Sixteen
Two people arrive at random inside the same hour and each waits fifteen minutes, so the reflex answer is a quarter. Drawing both arrival times as one point in a 60 by 60 square turns the question into an area, and the two corner triangles it leaves out have legs of 45, giving 7/16 rather than 1/4. The general formula n(2T-n)/T squared shows why the first minutes of patience buy the most.