This is the deep end. These riddles defeat most people on a first pass, and several defeat most people on a second. They are not harder because they are longer or more obscure - they are harder because they stack two pieces of misdirection where an ordinary riddle uses one.

Expert riddles are the right choice for a tie-breaker, for the last question of a quiz, or for the person who claims to be good at riddles. Give them one from this page and time how long the confidence lasts.

Every riddle has the answer and a written explanation, because at this level "the answer is a candle" is not enough - you need to see why nothing else fits.

If these are too much, Riddles for Adults sits one step down and is still not easy.

23.HardDark Riddle

I am the beginning of sorrow and the end of sickness. You cannot express happiness without me, yet I am in the midst of crosses. I am always in risk, yet never in danger. You may find me in the sun, but I am never out of darkness. What am I?

  • A.The heart
  • B.A tear
  • C.The letter A
  • D.The letter S
Answer: The letter S

The letter S starts "sorrow," ends "sickness," and appears inside each described word (happineSS, croSSeS, riSk, Sun, darkneSS).

Full explanation and related riddles

Frequently asked questions

Hard riddles usually rest on one piece of misdirection. Expert riddles stack two or more, or require you to reject an answer that fits everything except a single word.

The ones here are - every answer follows from the wording. The explanations exist precisely so you can check that after the fact.