20 Challenging Lateral Thinking Puzzles That Are Harder Than They Seem

These lateral thinking puzzles require some serious out-of-the-box thinking in order to solve.

Lateral thinking puzzles are designed to truly test your creative thinking skills. With these challenging riddles that require lateral thinking, you have to step outside the box and consider all the factors that could contribute to an answer that isn’t so obvious. This gives you a chance to put on your detective hat to try to solve these fun mysteries. Lateral thinking requires plenty of creativity, which is a great exercise for your brain.

The difference between lateral and vertical thinking

Lateral thinking differs from vertical thinking completely. When you’re thinking vertically, you’re going straight for the obvious and accepted answer, but with lateral thinking, you might come up with an alternative solution to a riddle that requires you to piece things together to come up with a creative answer. Fun, right? It encourages you to use creativity because, for most lateral thinking puzzles, there are a few ways you could come up with a “correct” answer. These solutions are more about creativity than correctness.

When you’re working on a lateral thinking puzzle, you have to look at the scenario presented and try to find context clues. Sometimes the most correct answer is actually the most obvious, which is why you don’t land there immediately. Other times the correct answer is really hard to get to because you have to create the rest of the scenario yourself to get there. If this sounds a little confusing, it’s because it is! But we pulled together some lateral thinking puzzles that will demonstrate how these riddles work. The answers are also provided with explanations so you can understand how to get to the solution. Check them all out and then quiz your brain with these logic puzzles next.

1. A woman lives on the 30th floor and hates taking the stairs. Every day she takes the elevator down to the lobby floor to go to work. When she comes home from work, she takes the elevator to the 20th floor and walks the rest of the way up, except on days when it rains. Those days she takes the elevator all the way home. Why does she walk the last ten flights of stairs if she hates it so much?

Answer: The woman is too petite to reach the button for the 30th floor. She can only reach the 20th floor button. On days when it rains, she uses her umbrella to hit the button for the 30th floor.

2. A man pushes his car until he reaches a hotel. When he arrives, he realizes he’s bankrupt. What happened?

Answer: He’s playing Monopoly and his piece is the car. He lands on a space with a hotel and doesn’t have the money to pay the fee.

3. A woman enters a room and presses a button. Within seconds she instantly loses 20 pounds. How did she lose the weight?

Answer: The room is actually an elevator. When she gets inside to go down, the elevator accelerates downward, making her weight temporarily lower.

4. A man who lives in a 30-story building decides to jump out of his window. He survives the fall with no injuries. How did that happen?

Answer: He may live in a 30-story building, but he only jumped out the window of the first floor.

5. A man is condemned to death. He has to choose from three rooms to accept his punishment. The first room has a firing squad with guns loaded. The second room has a blazing fire. The third room is full of tigers that haven’t eaten for six months. Which room should he choose?

Answer: The room of tigers. If the tigers haven’t eaten in six months, they’d be dead.

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6. A woman opened a door, screamed, and then was found dead a few minutes later. No gunshots were heard in the area. What happened to her?

Answer: She was on an airplane and opened the door while the plane was in flight, falling to her death.

7. Sam’s dad couldn’t keep his son from playing video games. To keep Sam from playing video games all the time, the dad grabbed a hammer and solved the problem. Now he can play video games but Sam cannot. What did the dad do

Answer: The dad built a shelf out of Sam’s reach and put the video game console up there. The dad can still reach it to play but Sam cannot.

8. After a night of partying with her friends, a woman arrives home and finds that she cannot enter the house. She’s sure that she’s at the right home, but she cannot get inside. What happened that makes entering her home impossible?

Answer: Her friends took her keys away from her the night before because she had too much to drink. They called her a cab to get home and kept her keys, which meant she didn’t have her house key.

Every two weeks a woman sits down and writes two words on 60 sheets of paper. Why does she do this?rd.com, Getty Images

9. Every two weeks a woman sits down and writes two words on 60 sheets of paper. Why does she do this?

Answer: The woman owns her own business with 60 employees. Every week she signs her name on their paychecks.

10. A woman enters a large metal tube. She’s terrified and holds her husband’s hand for comfort. He soothes her but is fine himself. A few hours later, the torment ends, and the woman is fine. What happened?

Answer: They were on an airplane and she’s scared of flying. Her husband, who isn’t scared of flying, tried to comfort her during the flight. She was fine once they landed.

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11. On a Sunday afternoon, a woman spotted a bear in the distance. Rather than be afraid, she ran toward it excitedly. Why wasn’t she afraid?

Answer: She was at the zoo.

12. Six pieces of coal, a carrot, and a scarf are lying on the lawn. Nobody put them on the lawn but there is a perfectly logical reason why they should be there. What is it?

Answer: A snowman was built in the yard, and the snow has since melted, leaving the eyes, nose, mouth, and scarf on the ground.

Three people enter a room but only two walk out. The room is empty. Where is the third person?rd.com, Getty Images

13. Three people enter a room but only two walk out. The room is empty. Where is the third person?

Answer: The third person was in a wheelchair and wheeled out.

14. A man is in a grocery store and fills a shopping cart. He walks out of the store without paying but no one stops him and no one calls the police. Why?

Answer: The man is an employee of the store and was filling the cart with trash to take out to the Dumpster.

15. A man walks into a bar and asks the bartender for a glass of water. The bartender pulls out a gun and points it at the man. The man says, “Thank you” and walks out.

Answer: The man had hiccups and the gun scared them out of him, to which he said, “Thank you.”

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16. If you were alone in a dark room, with only one match and an oil lamp, a fireplace, and a candle to choose from, which would you light first?

Answer: The match. You can’t light any of the rest of the objects without first lighting the match.

17. You are driving a bus. The bus is empty when you begin your route. At the first stop, three people get on. At the second stop, nine people get on and two get off. At the third stop, four people get off and two get on. What color are the bus driver’s eyes?

Answer: You are the bus driver —what color are your eyes?

18. A boat has a ladder that’s 10 feet long, and hangs off the side of the boat, with its last three feet submerged in water. If the ocean tide rises five feet, how much of the ladder will be underwater?

Answer: Still three feet. When the tide rises, the boat will rise with it, bringing the ladder along. No matter what, there will still be three feet submerged.

There are a dozen eggs in a carton. Twelve people each take a single egg, but there is one egg left in the carton. How?rd.com, Getty Images

19. There are a dozen eggs in a carton. Twelve people each take a single egg, but there is one egg left in the carton. How?

Answer: The 12th person takes the egg and the carton, leaving the egg inside.

20. A woman had two sons. They were born at the same hour on the same day of the same month in the same year. However, they were not twins. How could this be?

Answer: They’re triplets—there is a third child.

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Hedy Phillips
Hedy is a freelance writer for places including Best Life, POPSUGAR, InStyle, and more. She devotes 99% of her time to snuggling with her cats and 100% of her money to following Harry Styles around on tour. She's always on the lookout for another slice of New York pizza and she's never met a Starbucks drink she doesn't like.