We’ve collected 101 of the best trick questions to put your minds to work. Remember what makes these tricky is that the obvious answer is usually incorrect. There’s a hidden level of difficulty. You’re forced to think beyond your first solution.
However, the good news is that after taking on a few of these types of riddles, you begin to get the hang of it. Make it all the way through our list, and you’ll likely be prepared for just about any stumper.
If you’re looking for just one or two good brain teasers, our expert panel* has identified the top ten best ones just below. But, the more serious players will want to work their way down this whole page. Good luck – you just may need it!
Best Trick Questions With Answers
1.) 12 blackbirds sat on the branches of a tree. A man shot 1 blackbird with his gun. How many were left on the tree?
None. The rest flew away.
2.) What was the President’s name in 1992?
The same as it is today.
3.) John’s mother had three children. The first child was named April. The second child was named May. What was the third child’s name?
4.) Before Mount Everest was discovered, which was the highest mountain in the world?
5.) Imagine you are falling into a deep hole full of poisonous spiders and snakes. How would you survive?
Good Mind Trick Questions
6.) If you were running a race and passed the person in second place, what place would you be in now?
Second place. (If you passed the person in first place, you’d be in first.)
7.) A boy kicks a soccer ball. It goes 10 feet and comes back to him. How is this possible?
He kicked in up in the air right above him. Gravity!
8.) A truck driver is going down a one-way street the wrong way and passes at least five policemen. Why is he not caught?
He’s walking on the sidewalk, not driving at the time.
9.) How can you lift an elephant with one hand?
Don’t worry about it, as you won’t find one.
10.) If you had only one match and entered a dark room containing an oil lamp, a newspaper, and some kindling wood, which would you light first?
Tricky Riddles With Answers
11.) What do you call a woman who knows where her husband is all the time?
12.) A rancher had 500 cows and took one shot that got them all. How did he do it?
A panoramic photo.
13.) If you threw a red stone into a green sea, what would it come back as?
Wet. (Don’t overthink this.)
14.) How do you make the number one disappear?
Add the letter “g” to the front and it’s gone.
15.) How many sides does a circle have?
Two. Inside and outside.
16.) What gets bigger and bigger the more you take away from it?
17.) Why is it against the law for a man living in North Carolina to be buried in South Carolina?
You shouldn’t bury a person who is alive.
Hard Trick Questions
18.) What two words in combination hold the most letters?
Post and Office.
19.) In Nova Scotia you cannot take a picture of a man with a wooden leg. Why not?
You’d need a camera of some kind.
20.) You have two coins that add up to 30 cents, and one of them is not a quarter. Which two coins are they?
A quarter and a nickel – one is not a quarter, but one is.
21.) There was a terrible plane crash, every single person on board died, but yet two people survived. How is this possible?
The surviving couple was married.
22.) How many 6” by 6” books can you put in a (2ft x 2ft) container, so that it is not empty anymore?
One, after that, it is no longer empty.
23.) Which letter of the English alphabet flies, sings, and stings?
24.) John fell from a ladder 20 feet high. Yet, he was not hurt in the least. Why?
He was on the rung closes to the ground.
Hard Questions to Answer
25.) What gets broken without being held?
26.) What kind of tree can you carry in your hand?
27.) Some months have 31 days, and others have 30 days. How many have 28 days?
All 12 of them do.
28.) Which word in the dictionary is nearly always spelled incorrectly?
29.) What do an island and the letter “t” have in common?
They are both in the middle of water.
30.) She has married many men but has never been married. Who is she?
31.) What is at the end of a rainbow?
The letter “w”.
32.) What’s the best way to drop an egg on a concrete floor without cracking it?
Just drop it. The egg will likely crack, but the floor won’t.
33.) A woman dressed in all black is walking down a city street. Suddenly, a large black car without any lights on comes round the corner and screeches to a sudden stop. How did the car know the woman was there?
It was daylight.
34.) Can you spell enemy in three letters?
35.) I am an insect, and the first part of my name is the name of another insect. What am I?
36.) What wants to be answered but never has a question?
Brain Teaser Questions
37.) Is the capital of Kentucky pronounced Louisville or Luee-ville?
Neither. The capital is Frankfurt.
38.) The maker doesn’t want it; the buyer doesn’t use it, and the user doesn’t see it. What is it?
39.) What has 4 fingers and a thumb, but isn’t living?
40.) On which side of a chicken are there more feathers?
41.) What always ends everything?
The letter “g.”
42.) How can a man who shaves several times a day still sport a long beard?
He’s a barber.
43.) What coat goes on best wet?
A coat of paint.
44.) How many letters are in the alphabet?
11 letters are in “the alphabet.”
45.) How do you go 20 days without sleep?
Sleep at night.
46.) If Brenna had 4 piles of sand and Sara had 5 piles of sand, and they put them all together, how many piles would there be?
One big pile!
47.) The teacher asked the two girls who looked exactly like the following questions: a.) Are you from the same family? b.) Do you have the same parents? c.) Were you born on the same day? They answered truthfully “yes” to those questions, and yet told the truth when they indicated they were not twins. How can this be?
They were triplets.
48.) How long is the answer to this question?
49.) John’s father had three sons: Snap, crackle and …. who?
50.) What are the next three letters in this sequence: OTTFFSS?
ENT. One, two, three…It’s the first letter to every number counting up from one.
51.) John is a butcher. He is 5’ 10” tall and wears a size 11 shoe. What does he weigh?
52.) What is full of holes, but still holds liquid?
53.) A man claimed to have special powers, by saying that he could predict the score of any baseball game before it began. And, he was right. How did he do it?
The score is 0 – 0 before the game begins.
Trick Questions For Kids
54.) A woman pushes her car to a hotel and then proceeds to tell the owner that she is bankrupt. Why?
She’s playing the game of Monopoly.
55.) What’s the next number in the sequence: 8 5 4 9 1 7 6 10 3 _?
Two. The numbers are in sequence by the alphabet.
56.) Brothers Ben and Bob went and played checkers in the park. Each played 5 games. Ben told his mother he won 4 games. Bob told his mother he won 3 games. Both were telling the truth. How was this so?
They didn’t play against each other.
57.) In a lake, there is a patch of lily pads. Every day, the patch doubles in size. If it takes 50 days for the patch to cover the entire lake, how long would it take for the patch to cover half the lake?
49 days. Because when it doubles on that day, it will have covered the entire lake.
58.) Why was six afraid of seven?
Because seven, eight [ate], nine.
59.) What is round and extremely violent?
A vicious circle.
60.) How do you know when a clock is hungry?
It goes back four seconds.
61.) What word is the longest in the English language?
Smiles, because there’s a mile between the start and finish. Check out the more straightforward answer to the longest word.
62.) How do you catch a unique animal?
Unique up on ‘em.
63.) How do you catch a tame animal?
The tame way.
64.) Why do hippos wear red sneakers?
To hide in cherry trees.
Have you never seen a hippo in a cherry tree?
See how well it works?
65.) What did the person who invented the door-knocker win?
The No-bell prize.
66.) Which one is correct? “Penguins flies” or “A Penguin flies”?
Neither, a penguin doesn’t fly.
67.) Who is bigger, Mr. Bigger, Mrs. Bigger, or their baby?
Their baby is a little Bigger.
Check out more Funny Riddles.
Funny Brain Teasers
68.) How do you put an elephant in a refrigerator?
Open the door, put the elephant in, and close the door.
69.) How do you put a giraffe in a refrigerator?
Open the door, take the elephant out, lead the giraffe in, and close the door.
70.) The Lion King throws a party and invites every animal. All the animals attend except one. Which one?
The Giraffe. He’s still in the refrigerator.
71.) You receive an invite to the Lion King’s party. Five miles from Lion’s house, you have to cross a river noted for being full of crocodiles. How do you get across?
Swim across. Remember, all of the animals except the giraffe are at the party.
72.) A rope tied to a bull’s neck is 10 feet long and his food trough is 15 feet away. How did the bull eat successfully without breaking the rope or cutting it?
Walked over. The rope wasn’t tied to anything beyond the bull’s neck.
73.) Four football players stood under one umbrella and didn’t get wet. How could that be?
It wasn’t raining.
Trick Questions Image
74.) How could Tom go outside into the pouring rain without a hat or any protection, and yet not have a hair on his head got wet?
Show the answer: Tom was bald.
75.) The cowboy rode his mule into town. Why?
He couldn’t carry it.
76.) If an electric train is moving north at 100mph and a wind is blowing to the west at 10mph, which way does the smoke blow?
An electric train has no smoke.
77.) A rooster laid an egg on top of the barn roof. Which way did it roll?
It didn’t roll as roosters don’t lay eggs. Hens do.
78.) What goes up and down but still remains in the same place?
79.) How many times can you subtract 10 from 100?
Once. The next time you’d be subtracting 10 from 90.
80.) A plane crashes on the border of the U.S. and Canada. Where do they bury the survivors?
You don’t bury survivors…only the dead.
81.) Which president is on the U.S. $100 bill?
There isn’t one. Benjamin Franklin was never the president.
82.) How far can you walk into the woods?
Half-way. After that, you’re walking out of the woods.
83.) If I have it, I don’t share it. If I share it, I don’t have it. What is it?
84.) Tom’s father has five sons named: Ten, Twenty, Thirty, Forty and…guess what would be the name of the fifth?
Tom would be the fifth son.
85.) Two mothers and two daughters went out to eat, everyone ate one slice of pizza, yet only three slices were eaten. How’s that possible?
The group eating included a grandmother, her daughter, and her daughter’s daughter.
86.) How do you interpret this: “Ban ana”?
87.) How about this:
88.) Try this: “land time”
The land before time.
89.) And this one:
90.) A hard one…what does this mean?
A grave error. (Should read “RIP”)
91.) An easier one:
Age before beauty.
92.) Love this one:
pol mom ice
93.) And one more:
94.) Harder than you think…
95.) Can you name a word that is pronounced differently when the first letter is capitalized?
Herb or Polish.
96.) What’s the answer here?
97.) How about this?
Read between the lines.
98.) And this?
A pic in kle
In a pickle.
99.) Try this:
Three degrees below zero.
100.) If you have three, you have three. If you have two, you have two. But, if you have one, you have none. What is it?
Most Famous Trick Question Ever
101.) The Greeks believed that the Sphinx of Egypt would devour all travelers who could not answer correctly the riddle it posed, “What is the creature that walks on four legs in the morning, two legs at noon, and three in the evening?” This is a great example of a What Am I Riddles
The Greek hero Oedipus came up with the winning answer, “Man.” This caused the Sphinx’s death.
So, the moral of the story is that if you know the answers to tricky riddles, you have a lot of power. Do you now want to go back and review the answers above one more time?
— Tim Moodie and Mike O’Halloran
Our *expert panel: Tim, a writer and toy inventor, and Mike, a writer, and editor of Greeting Card Poet, have always loved a good riddle, brain teaser, and trick question. Yet, even in putting this collection together, they were stumped more than a few times.
They wholeheartedly agreed to leave one of the best-known questions off the list, “Have you stopped beating your wife?” But, then things got challenging. Through lots of giving and take, they arrived at the fine-tuned list above which they think are great for classrooms, dinner tables, and car rides.
You’re on the Trick Questions page.
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