wooden puzzle pieces with question marks on them.
Mayukh Saha
Mayukh Saha
January 26, 2022 ·  3 min read

Test: 18 Challenging Riddles That Could Keep You Up All Night Long

Most of us are guilty of spending all our free time scrolling through the same three social media apps. Our brains get duller as social media and other apps consume us. The lack of mental exercise can leave us feeling disconnected and dull. Taking some time out for riddles is a good way to keep our brains sharp. 

Riddles are one of the most satisfying and healthy mental exercises. 

The additional satisfaction of solving a tough riddle is unrivaled. It makes you feel good about yourself. A healthy mind is key to having a meaningful life.

If all that has convinced you to try some riddles, then today we bring you 18 of them! But before you start solving them, here is a warning: they are built to test the limits of your intelligence. So do not feel unhappy if you are unable to solve some of them. Some of them are really tough!

Here Come The Riddles

1. Mikasa drove to San Francisco in 3 days. At the end of her journey, she realized that one of her tires was flat. So how did she reach San Francisco?

2. Eren pointed to a boy on the street and said that the boy was the son of his grandmother’s only son. How is the boy’s family related to Eren?

3. The more you touch, the more of me you leave behind. What am I?

4. I am full of holes but I can hold a lot of water. What am I?

5. A bus driver was going the wrong way on a one-way street. Why do the police see him but not say anything?

6. I spend all my time on the floor but never get dirty. What am I?

7. What question can you never answer yes to?

8. A rooster laid an egg on a sloping roof. Which way with the egg roll?

9. What is as big as a lion but weighs nothing?

10. Peel off my skin. I won’ cry but you will. What am I?

11. When you don’t have me, you don’t want me, but when you have me you don’t wanna lose me. What am I?

12. First, they threw away my exterior then cooked my insides. Then they ate my outsides and threw away my insides. What am I?

13. A boy bought 12 tomatoes but when he reached home all but 9 were not crushed. How many tomatoes were in good shape?

14. A man is sitting in his cabin in Michigan. 3 hours later he stepped out of his booth in Texas. How is it possible?

15. John fell from a 20-meter ladder. However, he was not injured in the slightest. Why?

16. Connie called Sasha that he would be home at 9. He arrived at 9:05. They had no special plans but Sasha was furious that he was late. Why?

17. There are 3 keys and 3 doors. How many tries will you need to figure out which key opens which door?

18. A boy was playing with a book. He tore out pages 7, 8, 100, 222, and 223. How many pages did he tear out?

The Answers

Take your time with the riddles. Some of them are simpler than the rest, but that does not mean you should underestimate them.

If you are sure about the answers, then here they are:

1. The flat tire was the spare tire of her car.
2. He is Eren’s brother.
3. Fingerprints. 
4. A sponge.
5. He is walking.
6. A shadow
7. Are you asleep yet?
8. A rooster does not lay eggs.
9. The lion’s shadow
10. An onion.
11. A lawsuit.
12. An ear of corn.
13. 9 tomatoes
14. He is a pilot. The man is in the cockpit of an airplane.
15. He was on the rung closest to the floor.
16. Connie should have come home by 9 pm but he came home at 9:05 am the next day.
17. 6 attempts. 3 times for the first door. 2 times for the second door. Once for the last door.
18. 3 sheets

So how many of them did you get correct? Let us know in the comments below! Also, be sure to challenge your family and friends with this riddle quiz.

Here are some more challenging riddles for you: