50 Trick Questions Guaranteed to Leave You Stumped

Put on your thinking cap and try answering as many of these trick questions as you can—don't be shocked if you're left stumped!

How many of these trick questions can you answer correctly?

There’s nothing like tackling a good brain teaser to sharpen your memory and boost your brain power. Some of the best brain teasers to take a stab at? Trick questions. Trick questions require you to think outside the box and really get your brain churning for answers. Let’s see how many of these 50 trick questions you can answer correctly—no cheating! And if you’re looking for more ways to put your brain to the test, check out these hard riddlesriddles for adults, and “what am I?” riddles.

1. How many letters are in the alphabet?

11 (“the alphabet”)

2. If you build a fort, drive a Ford, and fill out a form, then what do you eat soup with?

A spoon

3. You have two coins that equal 30 cents, and one of them is not a quarter. Which coins do you have?

A quarter and a nickel (the nickel is the one that isn’t a quarter)

4. If the assistant captain of a sports team were to die, who would lead the team?

The captain

5. If there are eight oranges in a bag and you take away two, how many do you have?


6. If seven adults can eat seven cupcakes in seven minutes, how long would it take 30 adults to eat 30 cupcakes?

Seven minutes; one adult takes seven minutes to eat a cupcake

7. What is the answer to this question?


8. If Mrs. Smith’s rooster lays an egg in Mr. Brown’s yard, who owns the egg?

No one; roosters don’t lay eggs

Months Trick Questionrd.com

9. Some months have eight letters in their name, whereas others have five. How many have three?

They all do

10. What has five fingers but isn’t a hand?

A glove

Here are more brain games that will sharpen your mind (in a fun way)!

11. Ted is the father of Sam, but Sam is not the son of Ted. How is that possible?

Sam is not a boy

12. A deli worker in a grocery store is described as being 6’1″, wears size 10 shoes, and wears a medium-sized shirt. What does the deli worker weigh?

Lunch meat

13. A suspected burglar is brought in for questioning for a robbery that happened on the 4th of July. He tells the police he has an alibi, as he was home at the time of the robbery. A mailman comes in to the police station and verifies that he saw the suspect at home at the time of the robbery while on his mail route. The police, however, immediately know the mailman is lying. How?

The mail doesn’t run on the 4th of July, so there’s no way the mailman could have seen the suspect on his mail route. Check out more cool detective riddles.

14. What babbles but never talks?

A brook

Teeth Trick Questionrd.com

15. What’s something that has teeth but can’t chew?

A comb

16. A man once said he went 35 days without sleep. How is that possible?

He slept at night

17. What’s something that always wants an answer but doesn’t have a question?

A phone

18. You can catch me, but I can’t be thrown. What am I?

A cold

19. A woman quickly realizes there is no air in her driver’s side tire, but she finds something else in the tire instead. What is it?

A hole

20. What’s something that gets wetter the more it dries?

A paper towel

21. Sandy claims she saw an ocean without water, and it turns out, she was being honest. How is that possible?

Sandy saw the ocean on a map

22. What happens when you throw a blue rock into the Red Sea?

It sinks to the bottom

23. How can you drop a glass vase on a hardwood floor and not crack it?

Hardwood floors are hard to crack

24. What’s something that copies your looks but not your sounds?

A mirror

25. I wave, even if you don’t say hello. What am I?

A flag

Ladde Trick Questionrd.com

26. Al fell from a 30-foot ladder but didn’t get hurt. How is that possible?

He fell from the bottom rung

27. What word becomes longer after you add two letters to it?


28. What’s something that has a lot of holes in it but can still hold water?

A sponge

29. Two is a duo, and three is a trio. So what do four and five make?


Now, let’s see how many of these math riddles you can solve.

30. Which word in the dictionary has an odd spelling?


31. What’s something you can break but can’t put back together?

A promise

32. How many times can you cut a cake in half?

Technically, only once

Warm Cool Trick Questionrd.com

33. What’s something that gets warmer the more it cools?

An air conditioner

34. What are two things you can’t eat for dinner?

Breakfast and lunch

35. What’s something you can you hold without touching it?

Your breath

36. Let’s say you have to lift a hippo with one finger. How would you do it?

You wouldn’t because you can’t find a one-fingered hippo

37. What’s something that has a lot of problems not many people are eager to solve?

A math book

38. If you were in a race and passed the person in third place, what place would you be in?

Third place

39. A woman goes into the forest and sees ten trees. She then proceeds to snap all their branches at once. How is this possible?

She took a picture of the trees

40. What was the president’s name in 1990?

The same as it is today

41. What has a spine but no bones?

A book

Every Single Person Trick Questionrd.com

42. Every single person at a restaurant got sick, except for two people who were completely fine. How is that possible?

The two people were a couple and, therefore, not single

Want another challenge? Let’s see how many of these tongue twisters you can say without stumbling.

43. What’s something that has a head and a tail but no paws?

A quarter

44. Is it normal for someone to have all their toes on one foot?

No, as people’s toes are on two feet, not one foot

45. Which word in the dictionary is always spelled incorrectly?


46. What’s something that always rises and never lowers?

Your age

47. What gets larger the more you take away from it?

A hole

48. What’s something that belongs to you, but others seem to use it more than you?

Your name

49. A group of ten ostriches are in a field. If four of them take off flying, how many are left in the field?

Ostriches can’t fly

50. How many sides does a house have?

Two: an inside and an outside

Want another round of brain games? Let’s see how many of these lateral thinking puzzles you can solve.

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Kelly Kuehn
Kelly Kuehn is an assistant editor for Reader’s Digest covering entertainment, trivia, and history. When she’s not writing you can find her watching the latest and greatest movies, listening to a true crime podcast (or two), blasting ‘90s music, and hiking with her dog, Ryker, throughout New England.