25+ Tricky Riddles for Smart People Like You

Tickling neck tricky riddles

When young, growing up, we would binge tricky riddles sessions with our mother just before sleep.

She was a teacher and as a family tradition that was developed as I grew up, parts of the evening involved narrating what we learned in school for that day. If we did well, we would be rewarded with riddles and stories in return.

Such simple traditions made evenings the liveliest and the happiest times for the whole family. It also motivated us to learn as much as we can during the day so that in the evening, we have a story or two to tell about Math, Science, History…, etc.

If you are looking for ways to make your evenings lively as a family, these tricky riddles I have curated will help you achieve just that.

You can also incorporate other riddles, one theme at a time and make sure you never run short of riddles and jokes to surprise the little ones.

Tricky Riddles for Smart People

1. Crossing the River

Riddle: Two people are standing on the bank of a river looking forward to crossing to the other side. There is one boat with a capacity for one person. The two people managed to cross the river safely. How did they do it?

Answer: The two were on opposite sides of the river

2. Day After Tomorrow

Riddle: If the day after tomorrow becomes yesterday, today will be as far from Sunday as the day it was today when the day before yesterday was tomorrow. What day is it?

Answer: Sunday

3. Instagram Influencer

Riddle: Jemimah posted a photo on Instagram. How many people liked it if these statements are true? (1) Jemimah got at most 100 likes. (2) Jemimah got fewer than 100 likes. (3) Jemimah got at least 1 like.

Answer: Jemimah got 0 likes!

4. The 100 Dollar Bill

Riddle: A seller is selling his merchandise for $40 each. A customer approached him to buy one of the items with a 100 dollar bill at hand. The seller doesn’t have the change and so, he goes to his neighbor for it. After the customer has left, they discovered the 100 dollar bill was fake and the seller had to refund his neighbor with a $100. How much money did the seller lose?

Answer: $100. The merchandise was 40 and the change was $60. That is the amount of money the seller lost

5. The Family Limousine Riddle

Riddle: Three fathers and three sons are in a Limousine heading to a wedding ceremony for their youngest son. The total number of people inside the car is four. How is this possible?

Answer: Inside the car is a great-grandpa, grandpa, father and a son who is the bridegroom

6. Bachelorette Party

Riddle: In a bachelorette party attended by a group of 100 close friends, someone poisoned the drinks and every single person died. However, 25 miraculously survived. How comes this happened?

Answer: The 25 who survived were not single. They were either engaged or married.

7. The Last Born

Riddle: Himiko’s mother had three children. The firstborn is called Sunday and the second child is Monday. What is the name of the last born?

Answer: Himiko

8. Green Energy Cars

Riddle: If an old electric car at 70 miles per hour is heading south on an expressway on a calm day. Which direction will its smoke travel in?

Answer: None. Electric vehicles have zero emissions

9. Tricky Riddles for Teenagers

Riddle: Where I am, yesterday follows today and tomorrow is in the middle. Where am I?

Answer: In the dictionary

10. The Alphabet

Riddle: How many letters are there in alphabet?

Answer: There are 11 letters in alphabet. And there are 26 letters in the alphabet

11. The Riddle about Adopted Children

Riddle: A lady was asked about the number and ethnic composition of the children she is said to have adopted and her answer was: they are all Rwandese but two, all Albanian but two and all Nepalese but two. How many children did the lady adopt?

Answer: Only three. One fro Rwanda, one from Albania and one from Nepal

12. An English Word

Riddle: I am an English word. My first two letters refer to a male and my first three letters refer to a female. What am I?

Answer: Her

13. Train from Paris to Moscow

Riddle: A train from Paris to Moscow derailed at River Rhine while entering Germany from France. Its tail was in France while the head was in German soil and most parts were in no man’s land. Where will the survivors be buried in?

Answer: We don’t bury survivors but the dead!

14. Tricky Riddles for Kids

Riddle: I am an English word. The first two letters mean I am a male. The first three letters mean I am female. The first four letters mean I am a great man. And, the whole seven letter word means I am a great woman. What am I?

Answer: Heroine

15. The Penguin

Riddle: Unlike other birds, penguins don’t fly. They swim like fish and stand upright like a human being. Can a penguin call itself a bird?

Answer: Nope. Penguins don’t speak.

16. The 10 Meter Ladder

Riddle: Esperanza jumped from a 10 meters ladder and never hurt any part of her body. How comes?

Answer: She must have jumped from the first step of the 10 meters ladder

17. The Riddle of the Apple Tree

Riddle: Five pines are growing on a farm and every pine has 10 branches. If each branch bears 10 apples, how many apples will the farmer have?

Answer: None. Since when did pines start bearing apples?

18. Drawing a Circle

Riddle: If you are given a ruler, a compass, a protractor, a pencil and a piece of paper and asked to draw a circle and dissect it. What is the most logical first step to take?

Answer: Pick a piece of paper first

19. Tricky Riddles for Kids

Riddle: How many oranges would one eat on an empty stomach?

Answer: Just one. After the first orange, the stomach won’t be empty anymore

20. Family Fun

Riddle: A family of five is busy on a Sunday afternoon. The father is ironing. The mother is preparing meals. The firstborn child is playing chess and the last born is playing with the dog. What will the second-born be doing?

Answer: Playing chess with the firstborn

There you have our best tricky riddles for you.

Watch the Video Below:

tricky riddles for kids and adults

More riddles for you:

Easy Riddles with Hidden Tricks

Hard Riddles with Simple Answers

Super Funny Riddles for You

Good Riddles for Kids and Families

Dirty Riddles for the Naughty Minds

A List of the Best Riddles You’ll Ever Need

Tricky riddles