Hard Riddles (With Answers) That'll Leave You Totally Stumped

When was the last time you challenged yourself with a riddle? Riddles are a fun way of testing your critical thinking skills, encouraging you to examine your assumptions, look for alternate meanings, and think more creatively. The brain-flexing value of a good riddle doesn't go away as you grow up; word puzzles like these can help you stay sharp. So read on for 60 hard riddles that will get your gears turning.

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60 Hard Riddles (With Answers)

Whether you're looking for a way to break the ice, keep your company entertained, or simply see what you've really got going on upstairs, these puzzles are sure to help. And don't worry, answers are included. Now, read on to get started!

Tricky Riddles

1. Riddle: Without a bridle or a saddle, across a thing I ride a-straddle. And those I ride, by help of me, though almost blind, are made to see. What am I?
   Answer: Eyeglasses.
2. Riddle: George, Helen, and Steve are drinking coffee. Bert, Karen, and Dave are drinking Pepsi. Following this pattern, is Elizabeth drinking coffee or soda?
   Answer: Coffee, just like all the other names with two e's. (Those with one "e" drank Pepsi.).
3. Riddle: What English word has three consecutive double letters?
   Answer: Bookkeeper.
4. Riddle: First, think of the color of the clouds. Next, think of the color of snow. Now, think of the color of a bright, full moon. Now, answer quickly: What do cows drink?
   Answer: Water.
5. Riddle: If you have me, you want to share me. If you share me, you don't have me. What am I?
   Answer: A secret.
6. Riddle: I am something people love or hate. I change people's appearances and thoughts. If a person takes care of themself, I will go up even higher. Some people might want to try and hide me, but I will show. No matter how hard people try, I will never go down. What am I?
   Answer: Age.
7. Riddle: What are the next three letters in this combination? OTTFFSS.
   Answer: ENT. Each represents the first letter of a number in a sequence beginning with "one." So what comes after six and seven? Eight, nine, and ten.
8. Riddle: I have only two words but thousands of letters. What am I?
   Answer: The post office.
9. Riddle: My thunder comes before the lightning. My lightning comes before the clouds. My rain dries all the land it touches. What am I?
   Answer: A volcano.
10. Riddle: I come from a mine and am surrounded by wood. I help others to express themselves. What am I?
    Answer: Pencil lead.
11. Riddle: I have cities, but not houses. I have mountains, but no trees. I have coasts, but no sand. What am I?
    Answer: A map.
12. Riddle: You're in a dark room with a candle, a wood stove, and a gas lamp. You only have one match, so what do you light first?
    Answer: The match.
13. Riddle: What can travel all around the world while remaining stuck in a corner?
    Answer: A stamp.
14. Riddle: You measure my life in hours, and I serve you by expiring. I'm quick when I'm thin and slow when I'm fat. The wind is my enemy.
    Answer: A candle.
15. Riddle: A woman was born in 1975 and died in 1975. At the age of her death, she was 22 years old. How is this possible?
    Answer: 1975 refers to the hospital room number, not the year.
16. Riddle: What can you hold in your right hand but never in your left?
    Answer: Your left hand.
17. Riddle: I have keys but no locks. I have space but no room. You can enter, but you can't go outside. What am I?
    Answer: A computer keyboard.
18. Riddle: It's best to put this coat on wet.
    Answer: A coat of paint.
19. Riddle: What has four fingers and a thumb but isn't alive?
    Answer: A glove.
20. Riddle: A woman shoots her husband. She plunges him underwater for several minutes, then hangs him. Right after, they enjoy a lovely dinner. What happened?
    Answer: She took a picture of him and developed it in her dark room.
21. Riddle: A is the brother of B. B is the brother of C. C is the father of D. So how is D related to A?
    Answer: A is D's uncle.
22. Riddle: A butcher stands six feet and one inch tall and wears size 12 shoes. What does he weigh?
    Answer: Meat.
23. Riddle: How much dirt is in a hole that measures four feet by four feet by five feet?
    Answer: None.
24. Riddle: What disappears the moment you say its name?
    Answer: Silence.
25. Riddle: 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.
26. Riddle: How can you physically stand behind your father while he is standing behind you?
    Answer: You are standing back-to-back with your father.

Math Riddles

27. Riddle: When Billy's asked how old he is, he replies, "In two years I will be twice as old as I was five years ago." How old is he?
    Answer: 12 years old.
28. Riddle: How is seven different from the rest of the numbers between one and 10?
    Answer: Seven is the only one with two syllables.
29. Riddle: Turn me on my side, and I am everything. Cut me in half and I am nothing. What am I?
    Answer: The number eight.
30. Riddle: 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: Four sisters and three brothers.
31. Riddle: Two girls were born to the same mother, on the same day, at the same time, in the same month, and in the same year—but they're not twins. How is this possible
    Answer: The girls are triplets.
32. Riddle: TEN = 20, 5, 14. MEN = 13, 5, 14. Using the same logic, what do WOMEN equal?
    Answer: WOMEN = 23, 15, 13, 5, 14. The numbers represent the letter's position in the English alphabet.
33. Riddle: What would be math teacher be doing with a piece of graph paper?
    Answer: Plotting something.
34. Riddle: Mr. Taylor has four daughters and each has a brother. In total, how many children does Mr. Taylor have?
    Answer: Five children because all of his daughters have the same brother.
35. Riddle: If an electric train is moving north at 55 mph and the winds blowing east at 70 mph, which way does the smoke blow?
    Answer: An electric train doesn't emit smoke.
36. Riddle: What is 3/7 chicken, 2/3 cat, and 1/2 goat?
    Answers: Chicago.
37. Riddle: If a zookeeper had 100 pairs of animals in her zoo, and two pairs of babies are born for each one of the original animals, then (sadly) 23 animals don't survive, how many animals do you have left in total?
    Answer: 977 animals (100 x 2 = 200; 200 + 800 = 1000; 1000 – 23 = 977).

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Funny Yet Challenging Riddles

38. Riddle: Who spends the day at the window, goes to the table for meals, and hides at night?
    Answer: A fly.
39. Riddle: Which word in the dictionary is always spelled incorrectly?
    Answer: "Incorrectly."
40. Riddle: It belongs to you, but everyone else uses it.
    Answer: Your name.
41. Riddle: First you eat me, then you get eaten. What am I?
    Answer: A fishhook.
42. Riddle: Who has a neck and no head, two arms and no hands?
    Answer: A shirt.
43. Riddle: You see a boat filled with people. It has not sunk, but when you look again you don't see a single person on the boat. Why?
    Answer: All the passengers are married.
44. Riddle: What gets bigger the more you take away?
    Answer: A hole.
45. Riddle: What has 10 letters and starts with gas?
    Answer: An automobile.
46. Riddle: How can you drop a raw egg onto a concrete floor without cracking it?
    Answer: Concrete floors are very hard to crack.
47. Riddle: Two fathers and two sons are in a car, yet there are only three people in the car. How?
    Answer: They are a grandfather, father, and son.
48. Riddle: Three different doctors said that Paul is their brother yet Paul claims he has no brothers. Who is lying?
    Answer: No one is lying because the three doctors are Paul's sisters.

Tough Riddles About Words and Linguistics 

49. Riddle: I belong in the month of December, but not in any other month. I am not a holiday. What am I?
    Answer: The letter "D."
50. Riddle: One of these words does not belong: Brawl, Carrot, Change, Clover, Proper, Sacred, Stone, Seventy, Swing, Travel.
    Answer: Carrot. It's the only word that does not become another word when you remove the first and last letters.
51. Riddle: White bird, featherless. Flying out of paradise. Flying over sea and land. Dying in my hand. What is it?
    Answer: A snowflake.
52. Riddle: I'm everywhere and a part of everyone. I am at the end of space and time and existence itself. What am I?
    Answer: The letter "E."
53. Riddle: 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."
54. Riddle: What word in the English language does the 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?
    Answer: Heroine.
55. Riddle: What comes once in a minute, twice in a moment, but never in a thousand years?
    Answer: The letter "M."
56. Riddle: How many letters are in the alphabet?
    Answer: There are 11 letters in the words "the alphabet."
57. Riddle: It cannot be seen, cannot be felt, cannot be heard, cannot be smelt. It lies behind stars and under hills, and empty holes it fills. It comes first and follows after, ends life, kills laughter.
    Answer: Darkness.
58. Riddle: With pointed fangs, I sit and wait; with piercing force, I crunch out fate; grabbing victims, proclaiming might; physically joining with a single bite. What am I?
    Answer: A stapler.
59. Riddle: If the prisoner tells a lie, he'll be hanged; if he tells the truth, he'll be beheaded. What can he say to save himself?
    Answer: "You will hang me."
60. Riddle: What English word retains the same pronunciation, even after you take away four of its five letters?
    Answer: "Queue."

Wrapping Up

That's it for our list of hard riddles! Be sure to check back with us soon for even more brainteasers. You can also sign up for our newsletter so you don't miss out on what's next!