Here's sort of a mathy one that doesn't involve gouging out sensory organs or committing suicide. Instead, it's only about trains. Nice, relaxing trains.
A man retires from his job and moves to the countryside. He's sick of the hustle-and-bustle of the city and decides never to even wear a wristwatch any more or even keep clocks in his house.
He's always enjoyed trains (as in railroad) though, and happens to live next to a railroad track. Each day, at a completely random time, he walks out to tracks and waits for a train. After watching a train go by he goes back home for the rest of the day and records whether the train was a yellow train or a red train.
After months and months of data, he notices that for every red train he has seen, he has seen about 5 yellow trains. (i.e. 5 yellow trains to every 1 red train.)
One day he goes into the town to get groceries and mentions this to the shopkeeper, who knows quite a lot about local trains and train schedules. The shopkeeper informs him that the trains are on a very tight schedule and the red train passes on the tracks near his house on the hour every hour (12:00, 1:00, 2:00, 3:00, etc.). And to the man's surprise, the shopkeeper also informs him that the red and yellow trains alternate, one after the other, also at a set schedule, and there are an equal number of red trains as yellow trains that pass on the tracks near his house. And those are the only trains that ever use those tracks. [Edit: by all that I mean the yellow trains are also on a fixed schedule. And for any given hour of the day, two trains will pass: one red and one yellow.]
How can this be? Why did he see so many more yellow trains than red trains?
Stipulations:
(a) The red trains and the yellow trains are all of equal size/length, and that size is rather short: just a couple of cars or so.
(b) Although trains are involved, this enigma has nothing to do with special relativity or the Doppler effect. They are just normal trains (albeit short ones) moving at normal train speeds.