pondering woman

How Fast Can You Solve This Tricky Riddle About Two Brothers?

There are many things that are strangely satisfying. Things like peeling the plastic off a new phone, popping bubble wrap, crunching leaves, and freeing a cake from a Bundt pan without any cracking. But solving a tricky riddle can feel more satisfying than them all. There’s the added feeling of being smart that makes riddles so intriguing and so addictive to solve.


So here are 12 riddles for you to try. They range from logical puzzles to wordplay that forces you to think outside the box. For an added challenge, give yourself a time limit to solve each one. The answers immediately follow the question, so don’t scroll until you’re ready to check your solution.


12 Tricky Riddles to Stump Your Brain

Riddle #1: The Ages of Two Brothers

Brad is 12. His brother, John, is 13. How is the 12-year-old older than his brother?


Answer: Brad is 12 years old and John is 13 months old. 


Riddle #2: Her Next Birthday

Jess was 10 years old on her last birthday and she will be 12 on her next birthday. How is this possible?

Answer: Today is her 11th birthday.


Riddle #3: Sharing Something Tricky

If you have me, you want to share me. If you share me, you don’t have me. What am I?


Answer: A secret.


Riddle #4: Everything and Nothing

Turn me on my side and I am everything. Cut me in half and I am nothing. What am I?


Answer: The number 8. When it’s placed sideways, it looks like the infinity symbol. But when it’s cut in half, it becomes two zeros.


Riddle #5: Crossing the Tricky River

A farmer needs to carry a fox, a chicken, and a bag of grain across a river. The only way across the river is via a little boat, which can only hold the farmer and one of the items at a time. Left alone, the chicken will eat the grain, and the fox will eat the chicken. But the fox won’t eat the grain, and neither of the animals will wander away. How does the farmer get everything across the river?


Answer: This is what the farmer should do:

  1. Take the chicken and cross the river.
  2. Return with an empty boat.
  3. Bring the grain across the river.
  4. Take the chicken back.
  5. Bring the fox across the river.
  6. Come back with an empty boat.
  7. And once again, take the chicken and cross the river. [1]

Riddle #6: In a Dark, Dark Room

You’re trapped in a dark room with a candle, a wood stove, and a gas lamp. You only have one match, so what do you light first?

Answer: The match

Riddle #7: The Wind is My Enemy

You measure my life in hours and I serve you by expiring. I’m quick when I’m thin and slow when I’m fat. The wind is my enemy. 

Answer: A candle.

Riddle #8: The Tricky Middle of Spring

What is seen in the middle of March and April but it can’t be seen at the beginning or end of either month?

Answer: The letter “R”

Riddle #9: A Boat Full of People

You notice a boat filled with people sailing on a lake. It hasn’t sunk or floated away, but when you look at the boat again, you don’t see a single person. Why?

Answer: All of the people on the boat were married.

Riddle #10: How Many Siblings Are There?

A girl has as many brothers as sisters, but each brother has only half as many brothers as sisters. How many brothers and sisters are in this family? 

Answer: There are four sisters and three brothers.

Riddle #11: The Tricky Key to the Answer

I have keys, but no locks and space, and no rooms. You can enter, but you can’t go outside. What am I?

Answer: A computer keyboard

Riddle #12: Getting Wet, Getting Dry

What gets wet while drying?

Answer: A towel. [2]

Looking for some more brain teasers, riddles, and puzzles? Check these out:


  1. “14 brainteasers and riddles only smart people can solve.” Insider. Lucy Yang. May 8, 2019
  2. “27 of the Hardest Riddles Ever. Can You Solve Them?Reader’s Digest. Molly Pennington, PhD. August 12, 2021
Sarah Biren
Freelance Writer
Sarah is a baker, cook, author, and blogger living in Toronto. She believes that food is the best method of healing and a classic way of bringing people together. In her spare time, Sarah does yoga, reads cookbooks, writes stories, and finds ways to make any type of food in her blender.