150+ Confusing Riddles that bent my mind

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I’ve always been fascinated by riddles, the kind that make your brain ache a little, your eyes squint, and your coffee go cold as you obsess over the answer.

So I decided to go all in and gather some of the most confusing riddles I could find.

Not the “what has four legs” kind of easy stuff, but the kind of riddles that make even adults pause mid-scroll and wonder if their logic circuits need a reboot.

Some of these will trip you up with wordplay. Others will wrap your thoughts in knots. A few might even make you groan once you read the answer (my favorite kind).

I’ve tested most of them on friends and family and let’s just say not everyone was ready. But that’s the fun of it.

So if you love riddles that twist your brain into pretzels, you’re in the right place. Take a deep breath, trust your gut, and prepare to overthink everything. Let’s get puzzling.

150+ Confusing Riddles that bent my mind

  1. The more you take, the more you leave behind. What am I?
    Answer: Footsteps

  2. I speak without a mouth and hear without ears. I have no body, but I come alive with wind. What am I?
    Answer: An echo

  3. A man who was outside in the rain without an umbrella or hat didn’t get a single hair on his head wet. Why?
    Answer: He was bald

  4. What comes once in a minute, twice in a moment, but never in a thousand years?
    Answer: The letter “M”

  5. Forward I am heavy, but backward I am not. What am I?
    Answer: The word “ton”

  6. What is always in front of you but can’t be seen?
    Answer: The future

  7. What can fill a room but takes up no space?
    Answer: Light

  8. The more you take away, the bigger I become. What am I?
    Answer: A hole

  9. What has keys but can’t open locks?
    Answer: A piano

  10. What can travel around the world while staying in the same corner?
    Answer: A stamp

  11. I am not alive, but I grow. I don’t have lungs, but I need air. What am I?
    Answer: Fire

  12. What disappears as soon as you say its name?
    Answer: Silence

  13. The more there is, the less you see. What is it?
    Answer: Darkness

  14. A girl has as many brothers as sisters, but each brother has only half as many brothers as sisters. How many brothers and sisters are there in the family?
    Answer: 4 sisters and 3 brothers

  15. What comes at the end of everything?
    Answer: The letter “g”

  16. You see a boat filled with people. It hasn’t sunk, but when you look again, you don’t see a single person. Why?
    Answer: All the people were married

  17. A cowboy rode into town on Friday. He stayed three days and left on Friday. How is this possible?
    Answer: His horse’s name is Friday

  18. What flies without wings and cries without eyes?
    Answer: A cloud

  19. What has a head, a tail, is brown, and has no legs?
    Answer: A penny

  20. What comes down but never goes up?
    Answer: Rain

  21. What has many teeth but can’t bite?
    Answer: A comb

  22. What is always running but never moves?
    Answer: Time

  23. What can be broken but never held?
    Answer: A promise

  24. What has hands but can’t clap?
    Answer: A clock

  25. What begins with T, ends with T, and has T in it?
    Answer: A teapot

  26. What gets wetter the more it dries?
    Answer: A towel

  27. You see me once in June, twice in November, but not at all in May. What am I?
    Answer: The letter “e”

  28. If two’s company and three’s a crowd, what are four and five?
    Answer: Nine

  29. What word is spelled incorrectly in every dictionary?
    Answer: Incorrectly

  30. What begins with an E, ends with an E, but only contains one letter?
    Answer: An envelope

  31. What invention lets you look right through a wall?
    Answer: A window

  32. What has one eye but can’t see?
    Answer: A needle

  33. I go in hard, come out soft, and am never the same. What am I?
    Answer: Chewing gum

  34. You answer me, although I never ask you questions. What am I?
    Answer: A telephone

  35. What can run but never walks, has a bed but never sleeps, and has a mouth but never talks?
    Answer: A river

  36. The more of me there is, the less you see. What am I?
    Answer: Fog

  37. What has legs but doesn’t walk?
    Answer: A table

  38. What can you hold in your left hand but not in your right?
    Answer: Your right elbow

  39. What can’t talk but will reply when spoken to?
    Answer: An echo

  40. What kind of coat is best put on wet?
    Answer: A coat of paint

  41. What belongs to you but other people use it more than you do?
    Answer: Your name

  42. If a plane crashes on the border between the US and Canada, where do they bury the survivors?
    Answer: Nowhere, because survivors aren’t buried

  43. I shave every day, but my beard stays the same. Who am I?
    Answer: A barber

  44. What begins with a P, ends with an E, and has thousands of letters?
    Answer: The post office

  45. What kind of tree can you carry in your hand?
    Answer: A palm

  46. What can be cracked, made, told, and played?
    Answer: A joke

  47. If you drop me, I’m sure to crack, but give me a smile and I’ll always smile back. What am I?
    Answer: A mirror

  48. What comes once in a year, twice in a month, four times in a week, and six times in a day?
    Answer: The letter “e”

  49. What begins with an “I” and can help you see?
    Answer: An eye

  50. What goes up and down without moving?
    Answer: A staircase

  51. What has cities, but no houses; forests, but no trees; and rivers, but no water?
    Answer: A map

  52. What has a neck but no head?
    Answer: A bottle

  53. What can be touched but can’t be seen?
    Answer: Someone’s heart or emotion

  54. What has four fingers and a thumb but isn’t alive?
    Answer: A glove

  55. What can you keep after giving it to someone?
    Answer: Your word

  56. What type of building has the most stories?
    Answer: A library

  57. What has a bottom at the top?
    Answer: Your legs

  58. What is so fragile that saying its name breaks it?
    Answer: Silence

  59. What word has three consecutive double letters?
    Answer: Bookkeeper

  60. What kind of band never plays music?
    Answer: A rubber band

  61. What’s easy to lift but hard to throw?
    Answer: A feather

  62. What can go up a chimney down, but not down a chimney up?
    Answer: An umbrella

  63. What’s full of holes but still holds water?
    Answer: A sponge

  64. What begins and has no end, and ends all that begins?
    Answer: Death

  65. What runs around the house but doesn’t move?
    Answer: A fence

  66. I have branches, but no fruit, trunk, or leaves. What am I?
    Answer: A bank

  67. What flies forever, rests never?
    Answer: Time

  68. What has no beginning, middle, or end?
    Answer: A circle

  69. What word starts and ends with an “e” but only contains one letter?
    Answer: Envelope

  70. The more you take, the more I grow. What am I?
    Answer: A debt

  71. What has one head, one foot, and four legs?
    Answer: A bed

  72. What travels faster: hot or cold?
    Answer: Hot, because you can catch cold

  73. What’s something you can’t give someone without keeping it yourself?
    Answer: Your word or a promise

  74. What is always coming but never arrives?
    Answer: Tomorrow

  75. What gets sharper the more you use it?
    Answer: Your brain

  76. What gets bigger the more you take away from it?
    Answer: A hole

  77. If you’re running in a race and pass the person in second place, what place are you in?
    Answer: Second place

  78. What has a heart that doesn’t beat?
    Answer: An artichoke

  79. What can you catch but not throw?
    Answer: A cold

  80. What’s always in the middle of nowhere?
    Answer: The letter “h”

  81. What occurs once in every minute, twice in every moment, but never in a thousand years?
    Answer: The letter “m”

  82. What can one not keep, two hold tight, and three tear apart?
    Answer: A secret

  83. What can be heard and caught but never seen?
    Answer: A remark or a cold

  84. The person who makes it doesn’t use it. The person who buys it doesn’t want it. The person who uses it doesn’t know it. What is it?
    Answer: A coffin

  85. What can you see once in a year, twice in a week, and never in a day?
    Answer: The letter “e”

  86. A man is pushing his car along a road when he comes to a hotel. He shouts, “I’m bankrupt!” Why?
    Answer: He’s playing Monopoly

  87. What’s greater than God, more evil than the devil, the poor have it, the rich need it, and if you eat it you’ll die?
    Answer: Nothing

  88. A word I know, six letters it contains, remove one letter and twelve remains. What is it?
    Answer: Dozens

  89. Which is heavier: a pound of feathers or a pound of bricks?
    Answer: Neither, they weigh the same

  90. Before Mount Everest was discovered, what was the highest mountain in the world?
    Answer: Mount Everest

  91. What’s so delicate that even saying its name breaks it?
    Answer: Silence

  92. A box without hinges, key, or lid, yet inside golden treasure is hid. What am I?
    Answer: An egg

  93. What has four wheels and flies?
    Answer: A garbage truck

  94. What’s the one question you can never answer yes to truthfully?
    Answer: Are you asleep?

  95. What has a beginning, a middle, and an end, but no content?
    Answer: An empty book or story structure

  96. What question can you never truthfully answer “yes” to?
    Answer: Are you dead?

  97. What gets broken without being touched?
    Answer: A heart

  98. What word starts with “e,” ends with “e,” and has one letter in it?
    Answer: Envelope

  99. What do you throw out when you want to use it and take in when you don’t want to use it?
    Answer: An anchor

  100. What is as light as a feather, yet the strongest person can’t hold it for more than a minute?
    Answer: Your breath

  101. What comes in the morning without being called, and is lost in the night without being stolen?
    Answer: The sun

  102. What has eyes but can’t see?
    Answer: A potato

  103. What five-letter word becomes shorter when you add two letters to it?
    Answer: Short

  104. I am the beginning of everything, the end of time and space, the beginning of every end and the end of every place. What am I?
    Answer: The letter “e”

  105. You can serve it but never eat it. What is it?
    Answer: A tennis ball

  106. The more you have of me, the less you see. What am I?
    Answer: Darkness

  107. What doesn’t have lungs but needs air?
    Answer: Fire

  108. What runs but never gets tired?
    Answer: A refrigerator or a clock

  109. What comes once in a second, twice in a decade, but never in a century?
    Answer: The letter “e”

  110. A man stands on one side of a river, his dog on the other. He calls the dog, who immediately crosses without getting wet or using a bridge or boat. How?
    Answer: The river is frozen

  111. I’m tall when I’m young and short when I’m old. What am I?
    Answer: A candle

  112. What has no bones but can break your heart?
    Answer: A promise

  113. What can’t be used until it’s broken?
    Answer: An egg

  114. You walk into a room with a match, a kerosene lamp, a candle, and a fireplace. Which do you light first?
    Answer: The match

  115. The more you take from me, the stronger I become. What am I?
    Answer: A black hole or debt

  116. If you have it, you want to share it. If you share it, you no longer have it. What is it?
    Answer: A secret

  117. I am always hungry, I must always be fed. The finger I touch, will soon turn red. What am I?
    Answer: Fire

  118. What comes in pairs but you use one at a time?
    Answer: Eyelids or gloves

  119. What gets sharper the more you use it but dulls when unused?
    Answer: Your mind

  120. What begins with a question and ends with confusion?
    Answer: A riddle

  121. What’s tall during the day but disappears at night?
    Answer: A shadow

  122. What is the longest word in the dictionary?
    Answer: Smiles (because there’s a mile between the first and last letters)

  123. What turns everything around without moving?
    Answer: A mirror

  124. What has four wheels and no engine?
    Answer: A shopping cart

  125. What comes in with two legs but leaves with four?
    Answer: A person carrying a chair

  126. What is seen in the middle of March and April that can’t be seen at the beginning or end of either month?
    Answer: The letter “r”

  127. What can bring back the dead, make us cry, make us laugh, make us young, is born in an instant, yet lasts a lifetime?
    Answer: A memory

  128. What is never used unless it is broken?
    Answer: A record or a secret

  129. If you throw a red stone into the blue sea, what will it become?
    Answer: Wet

  130. What cannot be seen, cannot be felt, cannot be heard, and cannot be smelt?
    Answer: The dark

  131. What comes but never arrives, is waited on by all, and leaves everything behind?
    Answer: Tomorrow

  132. What can’t be seen, only described, and disappears when noticed?
    Answer: A thought

  133. What changes when you name it?
    Answer: A riddle

  134. The person who makes it sells it. The person who buys it never uses it. The person who uses it doesn’t know they are. What is it?
    Answer: A coffin

  135. What has 13 hearts but no organs?
    Answer: A deck of cards

  136. What’s at the end of the rainbow?
    Answer: The letter “w”

  137. What comes in through your eyes but leaves through your mouth?
    Answer: Knowledge

  138. What is always around you but hard to see?
    Answer: Air

  139. What runs but never has legs, murmurs but never speaks, and dies in silence?
    Answer: A stream

  140. What must be broken to be helpful?
    Answer: A horse or a habit

  141. What belongs to you but is used more by others?
    Answer: Your name

  142. You can’t see me, but I’m there. You can’t touch me, but I affect you. I make you warm, then cold. What am I?
    Answer: The wind

  143. What’s the end of everything?
    Answer: The letter “g”

  144. What gets bigger the more you share it?
    Answer: Joy

  145. What can never be stolen, only given away, and once lost, is hard to get back?
    Answer: Trust

  146. What becomes shorter as you use it?
    Answer: A pencil

  147. What exists only when you believe in it?
    Answer: Faith or imagination

  148. What keeps going up but never comes down?
    Answer: Your age

  149. What kind of cup can’t hold water?
    Answer: A hiccup

  150. What flies when you’re having fun and crawls when you’re bored?
    Answer: Time

Conclusion

If you made it through all 150+ riddles and still have your sanity intact, well done, you’ve got one seriously nimble mind.

Or at least a stubborn streak strong enough to resist the urge to scroll down for answers too quickly (no judgment if you did).

I hope these riddles gave you something more than just answers.

Maybe a laugh. Maybe a pause.

Maybe a quiet moment where everything else melted away and all that existed was the question: what on earth is this talking about?

Keep them handy. Share them. Stump your smartest friends.

Or better yet, see how many of them you can remember the next time someone says, “Hit me with a good one.” You’ve got 150+ ready to go.

And if your brain hurts a little… welcome to the club.

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