The English language can be quite puzzling at times. It’s full of quirks, inconsistencies, and complex grammar rules that often leave even native speakers scratching their heads. Riddles utilizing wordplay and the idiosyncrasies of English provide an entertaining brain teaser for language lovers. In this article, we have compiled 101 riddles about the English language along with their answers. The riddles range from simple plays on words to more advanced grammatical stumpers. Solving these verbal conundrums is not only fun, but can also help improve your mastery of English vocabulary, spelling, syntax, and more. So grab a dictionary and get ready to give your language skills a real workout!
Riddles
Homophones
1. What English word has three consecutive double letters?
Bookkeeper – The word “bookkeeper” has three consecutive pairs of double letters: oo, kk, and ee.
2. I’m tall when I’m young, and I’m short when I’m old. What am I?
A Candle – Candles are tall when new and get shorter as they burn down.
3. What word in the English language does following: the first two letters signify a male, the first three letters signify a female, the first four letters signify a great, while the entire world signifies a great woman. What is the word?
Heroine – He = male, Her = female, Hero = great, Heroine = great woman.
4. What 5-letter word becomes shorter when you add two letters to it?
Short – Adding two letters gives you “shorter”.
5. Forward I am heavy, but backward I am not. What am I?
Ton – Ton and Not.
6. What word looks the same backward and upside down?
SWIMS – SWIMS remains the same when reversed and rotated 180 degrees.
7. What word begins and ends with an ‘e’ but only has one letter?
Envelope – The envelope has one letter inside it.
8. I’m tall when I’m young and short when I’m old. What am I?
Candle – Candles are tall when new and shorten as they burn down.
9. What 4-letter word can be written forward, backward or upside down, and can still be read from left to right?
Noon
10. What common English word contains all 5 vowels in alphabetical order?
Facetious – The vowels a, e, i, o, u appear in order in “facetious”.
Homonyms
11. What word pronounced differently becomes its antonym?
Invalid – Invalid (sick) vs. invalid (not valid)
12. I follow you all day long, but when darkness comes I’m gone. What am I?
Shadow
13. What 3-letter word can be placed in front of each of the following words to make a new word: ape, car, dress, fell, bell, vein, trap?
Vein – making vainape, vainer, veindress, veinell, veinbell, veinvein, veintrap.
14. What word reads the same forward and backward?
Noon
15. What English word contains the same letters as its meaning?
Queue
16. What is unique about the word “rhythm”?
It has no vowels.
17. What is special about the word “facetious”?
It contains all the vowels in alphabetical order.
18. What do the following words have in common: job, polish, herb?
They become their own antonyms when the first letter is removed (ob, olish, erb).
19. There is a five letter word that when 2 letters are removed becomes its own synonym. What is the word?
Empty (becomes the synonym “void” when EM are removed).
20. What eight letter word contains only one vowel?
Strengths
Homographs
21. What word can mean the opposite of itself?
Sanction – Sanction can mean “approve” or “penalize”.
22. I’m an insect and the first part of a table. What am I?
Ant-ler
23. What English word retains the same pronunciation, even after you take away four of its five letters?
Queue
24. I’m tall when I’m young and short when I’m old. What am I?
Pencil
25. What 5-letter word becomes shorter when you add two letters to it?
Short
26. Forward I am heavy, but backward I am not. What am I?
Ton
27. What word begins and ends with an ‘e’ but only has one letter?
Envelope
28. I have a head like a cat. I have feet like a cat. But I am not a cat. What am I?
Caterpillar
29. What word looks the same upside down and backwards?
Swims
30. What word in the dictionary is spelled incorrectly?
Incorrectly
Contronyms
31. What English word can mean two opposites?
Sanction (to allow vs to penalize)
32. What word can be a noun or a verb, positive or negative, active or passive?
Cleave
33. I’m a word that’s spelled with all consonants. Take away one letter and I still sound the same. What word am I?
Rhythms
34. What word becomes shorter when you add two letters to it?
Short
35. What word reads the same forward and backward?
Noon
36. What word contains another word within itself?
Anonymous (contains “noun”)
37. What word looks the same upside down and backwards?
Swims
38. I’m an insect and the outermost part of a tree. What am I?
Bark
39. What word can have several meanings: an intestinal obstruction, money held for safekeeping, or a place to park?
Tie up
40. I’m the beginning of eternity and the end of time and space. What word am I?
E
Palindromes
41. What English word reads the same backward as forward?
Noon
42. What 4 letter word can be written forward, backward or upside down and can still be read left to right?
Noon
43. My first is in pain but not in ache, my second is in boat but not in ship, my whole is used a lot but never purchased. What am I?
Rental
44. Poor people have it. Rich people need it. If you eat it you die. What is it?
Nothing
45. What word looks the same upside down as right side up?
Swims
46. What word begins and ends with an ‘e’ but only has one letter?
Envelope
47. What 5 letter word becomes shorter when you add two letters to it?
Short
48. Forward I’m heavy, but backwards I’m not. What am I?
Ton
49. I’m tall when I’m young, and I’m short when I’m old. What am I?
Candle
50. What word looks the same backward as forward?
Noon
Anagrams
51. What is unique about the word “rhythm”?
It has no vowels
52. Unscramble this word: eilmnte
Element
53. Unscramble this word: draeiblc
Blackbird
54. Unscramble this word: dlanhoiy
Holiday
55. Unscramble this word: nteca
Canteen
56. Unscramble this word: slcsohu
Schools
57. Unscramble this word: aerpln
Parlour
58. Unscramble this word: roscoite
Scissors
59. Unscramble this word: lpatnye
Entaply
60. Unscramble this word: dinerga
Danger
Puns
61. What do you call a funny mountain?
Hill-arious
62. Did you hear about the race between the lettuce and the tomato?
The lettuce was a “head” and the tomato was trying to “ketchup”!
63. Did you hear about the hungry clock?
It went back four seconds.
64. What do you call an elephant that doesn’t matter?
An irrelephant
65. Want to hear a joke about construction?
I’m still working on it.
66. What do you call a dog magician?
A labracadabrador.
67. Why don’t scientists trust atoms?
Because they make up everything.
68. What do you call a belt with a watch on it?
A waist of time.
69. Did you hear about the angry pancake?
He just flipped.
70. What do you call a funny mountain?
Hill-arious.
Rhymes
71. What English word retains the same pronunciation, even after you take away four of its five letters?
Queue
72. I’m tall when I’m young, and I’m short when I’m old. What am I?
A candle
73. What word becomes shorter when you add two letters to it?
Short
74. Poor people have it. Rich people need it. If you eat it you die. What is it?
Nothing
75. What does this rhyme describe? I come in winter, but never in summer. I appear at night, but never at day. I am often frightening, sometimes pleasing too. All around the world I fly, silently with wings as white as snow.
Snow
76. What word begins and ends with “e” but only has one letter?
Envelope
77. Forward I’m heavy, backward I’m not. What am I?
Ton
78. What word becomes shorter when you add two letters to it?
Short
79. I’m tall when I’m young, and I’m short when I’m old. What am I?
A candle
80. What is so fragile even saying its name breaks it?
Silence
Grammar & Spelling
81. I’m a word that’s spelled with all consonants. Take away one letter and I still sound the same. What word am I?
Rhythms
82. What is the only 15 letter word that can be spelled without repeating any letter?
Uncopyrightable
83. What is the shortest English word containing all 5 vowels?
Sequoia
84. What is the longest one syllable word in English?
Screeched
85. What do the following words have in common: job, polish, herb?
They become their own antonyms when the first letter is removed.
86. What word contains all 26 letters of the alphabet?
Alphabet
87. What common English word contains all 5 vowels in alphabetical order?
Facetious
88. What 8 letter word has kst in the middle, in the beginning, and at the end?
Inkstand
89. What common word has three consecutive double letters?
Bookkeeper
90. What word retains the same pronunciation even after removing four of its five letters?
Queue
Vocabulary
91. What word can mean “to unite” as well as “to divide”?
Cleave
92. I end all disputes and make matters right. The heartbroken think I’m out of sight. But lovers know I make everything all right. What am I?
Kiss
93. I’m something people love or hate. I can be cracked, made, or told. What am I?
Joke
94. I can fill a room or just one heart. Others can have me but I can’t be shared. What am I?
Loneliness
95. People buy me to eat, but never eat me. What am I?
Plate
96. What word reads the same backward and forward?
Noon
97. Forward I’m heavy, backward I’m not. What am I?
Ton
98. I’m light as a feather, yet the strongest person can’t hold me for much more than a minute. What am I?
Breath
99. What word becomes shorter when you add two letters to it?
Short
100. What is so fragile that saying its name breaks it?
Silence
Conclusion
How did you do with these English language riddles? The idiosyncrasies of English provide endless possibilities for puns, wordplay, and trick questions. Solving riddles is not only fun, but helps improve vocabulary, spelling skills, and familiarity with grammar rules. The English language is complex, nuanced, and full of exceptions to the rules – which makes unraveling riddles about it both challenging and satisfying. We hope you enjoyed these linguistic brain teasers! Let us know if you have any other favorites we should add to the list. Keep puzzling!
