100+ Challenging Riddles That Will Make You Think Twice

home insemination kit

These riddles will truly get your mental gears turning.

by Team Clever Minds
Updated: June 29, 2022
Originally Published: October 7, 2019

Remember the iconic quote, “Riddle me this, riddle me that”? You can channel your inner riddle master during family game night with our curated collection of the most perplexing riddles ever assembled. Delight in challenging your friends and family with riddles that range from humorous to deep, and everything in between.

Riddles do more than just entertain; they exercise your brain, enhancing your cognitive skills like problem-solving and unconventional thinking. They’re an excellent way to keep your mind sharp, so dive into this list and see how many you can solve! If you manage to get more than 20 right, you’re officially a genius (or at least quite clever) in our eyes!

1. What starts with T, ends with T, and has T inside? A teapot.
2. Which English word sounds the same even after you remove four of its five letters? Queue.
3. When you need me, you toss me away. When you don’t, you pull me back in. What am I? An anchor.
4. You don’t want me when you lack me, but once you have me, you don’t want to lose me. What am I? A lawsuit.
5. What word in English signifies a male with its first two letters, a female with its first three, a great with its first four, and a great woman in total? Heroine.
6. Combine two blackberries and five apples. What do you get? A house full of gadgets.
7. What always concludes everything? The letter “G.”
8. I am an odd number. Remove a letter, and I become even. What number am I? Seven.
9. Walk on the living, they don’t even whisper. Walk on the dead, and they mutter and grumble. What are they? Leaves.
10. The more you possess, the less you can see. What is it? Darkness.
11. Can you name three consecutive days without mentioning Sunday, Wednesday, or Friday? Yesterday, today, and tomorrow.
12. If a red house is built from red bricks and a yellow house from yellow bricks, what is a greenhouse made of? Glass; all greenhouses are made of glass.
13. What follows this sequence: JFMAMJJASON? The letter “D,” representing the first letter of each month.
14. Identify the outlier: CORSET, COSTER, SECTOR, ESCORT, COURTS. Courts, as all others are anagrams.
15. A man and his boss share the same parents but are not siblings. How can that be? He is self-employed.
16. What has four fingers and a thumb yet is not alive? A glove.
17. What is as light as a feather, yet even the strongest man cannot hold it for long? Breath.
18. What has a heart that doesn’t beat? An artichoke.
19. What cannot be utilized unless broken? Eggs.
20. Where do cows vacation? Moo York.
21. What am I when “today” comes before “yesterday”? A dictionary.
22. What’s golden and tidies up after you? A broom.
23. What moves without sight and cries without eyes? A cloud.
24. What descends but never ascends? Rain.
25. Round like an apple, deep like a cup, yet all the king’s horses can’t pull it up. What is it? A well.
26. What question can you never respond to with yes? Are you asleep yet?
27. What makes you younger? Adding “ng.”
28. I come from a mine and am surrounded by wood. Everyone uses me. What am I? Pencil lead.
29. What can illuminate an entire room without occupying any space? Light.
30. What has one head, four legs, and a single foot? A bed.
31. What consists of water but dies when placed in water? An ice cube.
32. I only lie down once – when I die. What am I? A tree.
33. I have four keys without locks, a space but no room. You can enter but can’t go inside. What am I? A keyboard.
34. What did the chewing gum say to the shoe? I’m stuck on you.
35. What can never fit into a saucepan? Its lid.
36. Feed me, and I will survive. Give me water, and I will perish. What am I? Fire.
37. What’s filled with holes but retains a lot of water? A sponge.
38. Not my sister nor my brother but still a child of my parents. Who am I? Myself.
39. What is always ahead of you but remains unseen? The future.
40. Why do you always find lost items in the last place you look? Because once you locate them, you stop searching.
41. You purchased me for dinner but never consume me. What am I? Cutlery.
42. What can be measured but not seen? Time.
43. How many letters exist in the alphabet? Eleven letters in “the alphabet.”
44. What can an elephant produce that no other animal can? A baby elephant.
45. I can be written, spoken, exposed, or broken. What am I? News.
46. Smell me, buy me, and deliver me; I won’t change. What am I? Scent, cent, and sent.
47. How do football players keep cool during a game? They stand next to the fans.
48. What kind of dress can’t be worn? Address.
49. What breaks in water but never on land? A wave.
50. Where does an alarm clock stay when it goes off? Right where it is.
51. My rings aren’t of gold, yet I gain more as I age. What am I? A tree.
52. What is found at the end of a rainbow? The letter W.
53. The more you take, the more you leave behind. What are they? Footsteps.
54. What has twelve faces and forty-two eyes? A pair of dice.
55. How many seconds exist in a year? Twelve – January 2nd, February 2nd, and so on.
56. As a stone within a tree, I help your words endure. But if you push me while I stand, the more I move, the less I am. What am I? A pencil.
57. What’s black when obtained, red when used, and white when finished? Charcoal.
58. You use a knife to behead me, yet you cry over my death. What am I? An onion.
59. Which bird can lift the most weight? A crane.
60. I appear twice in eternity and am always visible. What am I?
61. What can you hold in your right hand but never in your left? Your left hand.
62. What can you fill with empty hands? Gloves.
63. What is stronger than steel yet fears the sun? Ice.
64. What is spoken and broken almost immediately? Silence.
65. Forwards I’m heavy; backwards I’m not. What am I? Ton.
66. What has twelve faces and forty-two eyes? A pair of dice.
67. How do you make the number one vanish? Add a G, and it’s gone.
68. How many bricks are needed to finish a brick-made building? One – to “complete a building.”
69. What possesses a neck but no head? A bottle.
70. How can you burn an apple, blueberry, rose, and pumpkin without leaving ashes yet maintain their fragrance? By lighting scented candles.
71. What five-letter word becomes shorter when you add two letters? Shorter (Short + ‘er’).
72. Where there is light is where I thrive, but if light shines on me, I perish. What am I? A shadow.
73. What tastes better than it smells? Your tongue.
74. What can pass through glass without breaking it? Light.
75. What flies when born, lies when alive, and runs when dead? A snowflake.
76. What flows but doesn’t walk? Water.
77. What begins and has no end and is the conclusion of everything that starts? Death.
78. Which English word contains three consecutive double letters? Bookkeeper.
79. What appears in the middle of March and April but is absent at the start or end of either month? The letter “R.”
80. What time both begins and ends with “N”? Noon.
81. What word starts and ends with an E but contains just one letter? Envelope.
82. Where can you find cities, towns, shops, and streets but no people? A map.
83. What do you bury when it’s alive and dig up when it’s dead? A plant.
84. What spends all its time on the floor but remains clean? Your shadow.
85. What is so delicate that saying its name shatters it? Silence.
86. What has hands but cannot clap? A clock.
87. What has branches and leaves but no bark? A library.
88. Which type of tree can you carry in your hand? A palm tree.
89. What can you never get rid of when you actually lose it? Your temper.
90. What has one eye but cannot see? A needle.
91. What can you keep even after giving it to someone? Your word.
92. Why is an island comparable to the letter T? Because it’s in the middle of water.
93. How do we know carrots are beneficial for your eyesight? You never see rabbits wearing glasses.
94. What can you create that remains unseen? Noise.
95. What connects two people yet only touches one? A wedding ring.
96. What falls but never shatters? What breaks but never falls? Day and Night.
97. Who has wedded many women but has never been married? A priest.
98. What has a head and a tail but lacks a body? A coin.
99. If a brother, his sister, and their dog weren’t under an umbrella, why didn’t they get wet? Because it wasn’t raining.
100. What has teeth but cannot eat? A comb.

For more engaging content, check out our other articles, such as the at-home insemination kit for your journey to parenthood. Also, visit Make a Mom for trusted advice on home insemination methods. Additionally, IVF Babble is an excellent resource for pregnancy and home insemination information.

In summary, these riddles are a fun way to challenge your mind and engage with friends and family. They not only entertain but also sharpen your cognitive abilities. Dive in, enjoy, and see how many you can solve!