Have you ever wondered why we love riddles so much? Is it the double or veiled meaning they put forth, our penchant for puzzle solving, the intriguing opposition between two or more descriptive elements the referent of which must be identified, or simply the unexpected or witty answers? Whatever the reason, it explains why riddles are encountered in all cultures and recorded as early as Babylonian times. What they achieve is making ”a point of playing with conceptual boundaries and crossing them for the intellectual pleasure of showing that things are not quite as stable as they seem”. Although such head scratching may be exasperating, it does open our minds to a variety of possibilities. Both a folklore genre and a rhetorical device, these brain teasers charm us even when we have heard them before, and either challenge us to think or just make us laugh.

Thus, there are two main types of riddles: enigmas, which are problems whose solving requires attention and sharpness, using metaphorical or allegorical language, and conundrums (or riddle jokes), which are questions whose effects arise from punning, and whose answer is not actually expected, but rather constitutes a punch-line; more often than not, the latter will put translators’ skills to the test. And while many riddles are based on logic, others rely on linguistic techniques to make the guesser understand something other than the desired answer. This month we explore the playful side of language, and propose a tentative, non-exhaustive classification of such riddles, according to the linguistic concept or relationship they use.

1. Riddles based on the opposition between the form and meaning of a word

Subtypes include riddles where:

  • The question relates to spelling rather than meaning, and the answer is a letter:

E.g.: What occurs once in a minute, twice in a moment, but never in a thousand years? (Letter M)

  • The question does not relate to a feature, but to the word itself, and adding or removing letters leads to the answer:

E.g.: What word becomes shorter when you add two letters to it? (Short)

  • The question relates to meaning rather than spelling:

E.g.: How can you say “rabbit” without the letter R? (Bunny)

  • The answer is a reverse anagram of a word in the question:

E.g.: Forward I am heavy, but backward I am not. What am I? (Ton)

  • Conundrums are based on form rather than meaning:

E.g.: When is this sentence true: “There are eleven letters in the alphabet”? (When the alphabet is in quotation marks.)

  • Conundrums are based on letters and their inclusion in a word:

E.g.: Why is letter T like an island? (Because it is in the middle of water.)

2. Riddles based on homophony

Subtypes include riddles where:

  • The answer is homophonous and the question relates to both homophones:

E.g.: What is the coldest country in the world? (Chile)

  • One of the homophones in the question is a letter:

E.g.: What begins with T, finishes with T and has T in it? (A teapot)

  • The answer is a homophonous letter:

E.g.: Which letter of the alphabet has the most water? (Letter C)

  • The answer of a conundrum contains several words that together are pronounced like one or several words which relate to the question:

E.g.: Why will one never starve in the desert? (Because of all the sand which is there.)

  • The answer of a conundrum relates to the homophone of a word (or combination of words) in (or suggested by) the question:

E.g.: Why is six afraid of seven? (Because seven eight nine.)

3. Riddles based on homonymy

Subtypes include riddles where:

  • The question contains the homonym and suggests one word, and the answer relates to the other word with the same spelling and pronunciation:

E.g.: What starts with letter P, ends with letter E and has thousands of letters? (The Post Office)

  • The answer is the homonym, and the question combines the two meanings:

E.g.: What kind of tree can you carry in your hand? (A palm)

  • The question contains or suggests two words which form a compound that is the answer:

E.g.: What kind of nails do carpenters avoid? (Fingernails)

  • Conundrums contain homonyms:

E.g.: Why is letter E like London? (Because E is the capital of England.)

4. Riddles based on polysemy

Subtypes include riddles where:

  • The question puts forth one meaning of a word, and the answer relates to a second meaning:

E.g.: What has a neck, but no head? (A bottle)

  • The answer of a conundrum relies on a polysemous word:

E.g.: Why can’t a nose be twelve inches? (Because then it would be a foot.)

5. Riddles using compounds or word parts

Subtypes include riddles where:

  • The answer is a compound, and one of the words composing it is in the question:

E.g.: What kind of dog has the most ticks? (A watchdog)

  • The answer word is not a compound, but part of it is in the question:

E.g.: What’s a teacher’s favourite nation? (Expla-nation)

  • Conundrums use compounds or word parts:

E.g.: Why is the bluebird blue? (Because the mockingbird is always mocking him.)

6. Riddles containing idiomatic phrases

Subtypes include riddles where:

  • The answer and part of the question form an idiomatic expression:

E.g.: What is so delicate even saying its name will break it? (Silence)

  • The answer is derived from the literal rather than the idiomatic meaning:

E.g.: Who earns a living for driving customers away? (A taxi driver)

7. Riddles based on the transitive/intransitive distinction

E.g.: What gets wet when it dries? (A towel)


The list of riddles that follows is for your own enjoyment (answers are provided at the bottom of the page), and the genuine language lovers out there may even try to guess which type in our classification above they belong to.

  1. What can’t be used until it’s broken?
  2. What odd number becomes even when beheaded?
  3. What goes `Oh, Oh, Oh’?
  4. Why do the French only have one egg for breakfast?
  5. What letter is looking for causes?
  6. What is the longest word in the English language?
  7. How many seconds are in a year?
  8. What instrument is bound to make false notes?
  9. What word of only three syllables contains 26 letters?
  10. What four days of the week start with the letter T?
  11. In what way can letter A help a deaf lady?
  12. Why are baseball stadiums so cool?
  13. What room has no doors or windows?
  14. What country can you put on the table?
  15. What kind of bell doesn’t ring?
  16. How do you make the number one disappear?
  17. What do you call a pig with three eyes?
  18. What is at the end of the rainbow?
  19. Why can’t a bicycle stand on its own?
  20. What can you catch, but not throw?
  21. What letter can do the work in one day that you can do in two days?
  22. What’s a minimum?
  23. Why do cows have bells?
  24. What has four wheels and flies?
  25. What is the centre of gravity?
  26. What is in the army and is corny?
  27. What has many keys but can’t open any door?
  28. What loses its head in the morning and gets it back at night?
  29. How does an octopus go to war?
  30. What is as light as a feather, but even the strongest man couldn’t hold it for more than one minute?




1. An egg. 2. Seven. 3. Santa Claus walking backwards. 4. Because one egg is un oeuf. 5. Y. 6. “Smiles”, because there is a mile between the two S’s. 7. 12: January 2nd, February 2nd, etc. 8. A lyre. 9. Alphabet. 10. Tuesday, Thursday, today and tomorrow. 11. It can make her hear. 12. Because there is a fan in every seat. 13. A mushroom. 14. China. 15. A dumbbell. 16. Put a G in front of it. 17. A piiig. 18. Letter W. 19. Because it’s two-tired. 20. A cold. 21. W. 22. A very small mother. 23. Because their horns don’t work. 24. A garbage truck. 25. Letter V. 26. A colonel. 27. A piano. 28. A pillow. 29. Armed. 30. Breath.

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