These trick questions can be fun to ask your friends even your coworkers. Some are a play on words, others are just a little silly trick that will definitely keep you guessing.

Icebreaker games

Aside from these trick questions, you can find all kinds of difference icebreaker games over at Brightful Meeting Games. If you enjoy riddles, you will probably love playing Trivia too!

1. What word is spelled incorrectly in every single dictionary?


2. What goes up and down but can't move?

A staircase.

3. What goes up but never down?

Your age.

4. I have one head, one foot, and four legs. What am I?

Your bed.

5. Forwards I’m heavy but backwards I’m not. What am I?

A ton.

6. What runs, but never walks. Murmurs, but never talks. Has a bed, but never sleeps. And has a mouth, but never eats?

A river.

7. I have teeth but can’t eat. What am I?

A comb.

8. If I drink, I die. If I eat, I’m fine. What am I?

A fire.

9. I’m light as a feather, but not even the strongest girl can hold me for more than 5 minutes. What am I?


10. How can the pocket of your pants be empty, but still have something in it?

When the something is a hole.

11. A girl fell off a 50-foot ladder but didn’t get hurt. How come?

She fell off the bottom rung.

12. If two’s company and three’s a crowd, what do four and five make?


13. What gets bigger and bigger the more you take away from it?

A hole.

14. Is it legal for a man to marry his widow’s sister?

No, but since he is dead it would be hard to do so.

15. How did the boy kick his soccer ball ten feet, and then have it come back to him on its own?

He kicked it up.

16. What breaks and never falls, and what falls and never breaks?

Day breaks and night falls

17. What did one campfire say to the other?

Shall we go out tonight?

18. What happened when the wheel was invented?

It caused a revolution.

19. What has one eye but can’t see anything at all?

A needle.

20. What starts with “e” and ends with “e” but only has one letter in it?

An envelope.

21. How can a girl go 25 days without sleep?

She sleeps at night.

22. There was terrible plane crash, every single person onboard died, but yet two people survived. How is this possible?

The surviving couple was married.

23. A 10 foot rope ladder hangs over the side of a boat with the bottom rung on the surface of the water. The rungs are one foot apart, and the tide goes up at the rate of 6 inches per hour. How long will it be until three rungs are covered?

Never. The boat rises as the tide goes up.

24. What has a face and two hands, but no arms or legs?

A clock.

25. Mr. Jones noticed that his pants pockets were totally empty – but that there was still something in it. What was it?

A hole.

26. A is the father of B. But B is not the son of A. How’s that possible?

B is the daughter.

27. I’m so fragile that if you say my name, you’ll break me. What am I?


28. A man dressed in all black is walking down a country lane. Suddenly, a large black car without any lights on comes round the corner and screeches to a halt. How did the car know he was there?

It was day time.

29. What kind of tree can you carry in your hand?

A palm.

30 How can you drop a raw egg onto a concrete floor without cracking it?

The egg won’t crack the concrete floor!

31. What can one catch that is not thrown?

A cold.

32. What has a head and a tail but no body?

A coin.

33. A truck driver is going down a one way street the wrong way, and passes at least ten cops. Why is he not caught?

Because he was not driving! He’s walking on the sidewalk.