36 Riddles Teens Will Love + Answers (2023)

One of the best ways to engage the mind, and to keep it sharp as a tack is to engage in some riddles.

Riddles are fun to ponder, often leaving you thinking for multiple hours at a time, and once you find out the eventual answer, it can be incredibly amusing and satisfying.

The only trouble is, riddles can often be a little too difficult and are often a little too obtuse to carry the interest of some people. They can be especially unappealing to teenagers who may find some a little bit too difficult.

Want to know some of the very best riddles that can be enjoyed by teenagers? Want riddles that still offer a challenge but are not going to have your mind totally aching?

Then check out our comprehensive list of some of the very best riddles that teens will totally get a kick out of!

1.“I am lighter than a feather, but you cannot hold me for longer than two minutes. What am I?”

This is a fun riddle because it poses a truly fun question. What could be lighter than a feather, but still heavy to hold?

The answer to this riddle is actually ‘Breath’, as it is hard to hold your breath, but it is very light!

2. “The more I dry, the more I get wet. What am I?”

This is a totally classic riddle that has been shared for generations.

The answer to this riddle is ‘A towel’, as towels are made to suck up moisture from other objects!

3. “What has a neck but no head?”

It’s difficult to imagine any kind of creature having a neck, but not having a head.

The answer here, instead, refers to an object ‘A bottle’. Bottles are referred to as having ‘necks’, but you would never hear a bottle referred to as having a ‘head’.

4. “What is the similarity between “2+2=5”, and your left hand?”

This one has been known to stump people for a few minutes, but by the time the answer comes, it is incredibly satisfying. The answer is ‘Neither of them is right’!

5. “You can drop me from a tall building, and I will not be harmed, but drop me into the water, and I will fall apart. What am I?”

It can be difficult to imagine anything that can survive a fall from a tall building, but what if it were something light but structurally weak? In this case, the answer is ‘Paper’!

6. “If an electric train were to be traveling North, which way would the smoke from the train be traveling?”

Most people respond to this riddle with an emphatic “South”, but the answer is that the smoke travels nowhere, because electric trains don’t produce any smoke!

7. “What is the center of gravity?”

This riddle goes against standard convention, as we don’t normally think about anything being at the center of gravity. However, in this case, it refers directly to the word itself! Thus, the answer is ‘V’, the letter at the center of the word!

8. “In what case does divorce come before marriage?”

You’d assume that such a situation would be logically impossible, but in this case, the answer refers to the dictionary! Within the dictionary, the word ‘Divorce’ would naturally come first!

9. “I go up, but I never come back down. What am I?”

In this case, the answer is ‘Your age’! While gravity forces things to eventually come back down, time cannot be reversed, thus your age can never come back down!

10. “What weighs more: a pound of steel, or a pound of feathers?”

This particular riddle is very deceptive, as it quickly prompts people to respond with ‘A pound of steel’, but the answer is actually that they both weigh the same because they are both a pound!

11. “I’m an Uber driver, and I am going the opposite direction down a one-way street. However none of the five police officers that pass me stops me. Why is this?”

Surely traveling in the opposite direction of the street as an Uber driver would be dangerous, right? But what if the Uber driver was not currently driving, and was instead walking?

12. “There are two fathers and two sons sitting in a car. However, there are only three people actually sitting in the car. How is this possible?”

Surely this could not be possible, right? Well, in this case, this riddle is actually referring to three generations: Grandfather, father, and son. This would mean that logically there are two sons and two fathers!

13. “The trees are my home, though I am permanently outside, and if I fall from the tree, I will die. What am I?”

Can anywhere really be home if you are not inside it? In this case, the answer refers to leaves, which hang on the outside of the tree, yet depend on the tree for survival!

14. “I’m a cowboy, and I rode into town on Friday. I stayed in town for three days, and yet left town on Friday. How did I do this?”

In this case, you need to think about what the word “on” implies. In this case, when the cowboy says that they rode into town “on Friday”, they are actually referring to a living creature! In this case, “Friday” actually refers to a horse by the same name!

15. “I have four fingers and a thumb, but I am not actually alive. What am I?”

How could this be possible? What could possibly have fingers but not be alive? In this case, it refers to ‘a glove’, which has the shape of a hand, but is not alive!

16. “I can go through glass without breaking it. What am I?”

You’d think that being able to pass through glass would require the glass to break first, right? Glass is incredibly fragile, so what could possibly pass through it without causing damage?

In this case, the answer is ‘Light’! Which passes through windows.

17. “I start in little, but end in full. You’ll find me in both half and complete. What am I?”

This one will really get teens thinking quite hard, and have them questioning how they could possibly find the answer. In this case, it refers directly to the letter ‘L’ which can be found in all of these words at the positions described within the riddle.

18. “I am an odd number, but if you take away a letter, I become even. What number am I?”

This one really bends the mind, as it gets you wondering how it would be possible to remove a letter from a number and be met with an even number…

In this case, the answer is ‘seven’, because when you remove the letter ‘S’ from ‘Seven’, you will be left with the word ‘Even’.

19. “I am a word that is always spelled wrong. What word am I?”

Surely spelling a word wrong must be totally wrong, right? Well, in this case, a word that can easily be spelled wrong is actually the word ‘wrong’ itself! This is a riddle that will get people laughing once they receive the solution to it!

20. “ I am the only organ that managed to name itself. What organ am I?”

Our internal organs do not naturally have names and were given names over time by scientists. However, when you think about it, which organ was used in order to give a name to these organs? That’s right, ‘the brain’! Thus, the brain is the only organ that is able to name itself.

21. “I buy a number of eggs from the store, but by the time I get back home, all but six of the eggs have broken. How many are left unbroken?”

This is a very simple but humorous riddle that first prompts listeners to think a little too hard, coming up with all kinds of complicated answers. However, the answer is very simple, as the riddle is only asking how many eggs haven’t broken, which is ‘six’ of the eggs!

22. “What question can you never answer ‘yes’ to?”

This is a very humorous riddle, because the question that it refers to is one that has been asked countless times. The question that is being referenced is ‘Are you asleep?’. The answer to this riddle is sure to generate a laugh.

23. “What comes up to let us move, but goes down to hold us in place?”

This is another riddle that tests a teenager’s sense of logic, and their ability to tackle complicated logical issues.

The answer to this is quite simple, but it may take a while to arrive at it! In this case, this riddle is referring to an ‘Anchor’, which is used to hold ships in place despite the tide, but once pulled up allows the boat to move onward.

24. “What is heavy when pushed forward, but not backward?”

This is another riddle that is deceptively simple. The riddle invites you to begin questioning the logic to try and think about objects that could match this description. However, if you approach the riddle in a different way that instead focuses on the words, then the answer soon reveals itself.

In this case, the answer is a ‘Ton’, which is heavy to push, but when the word itself is spelled backward, it reads ‘Not’!

25. “What eight-letter word remains a word even as you remove letters from it one at a time?”

This is a riddle that many do not eventually figure out when asked, but when the answer is eventually revealed, it proves to be surprisingly satisfying!

The answer to this riddle is the eight-letter word ‘Spelling’, which can be reduced to the following words by removing one letter each time: ‘staring’, ‘string’, ‘sting’, ‘sing’, ‘sin’, ‘in’, and ‘I’. This is as much a fascinating fact as it is an intriguing riddle to ponder.

26. “Two people are playing chess, but both win. How is this possible?”

This is another riddle that will have people pondering all of the possibilities, but not the most obvious. The riddle does not stipulate that the two people are actually playing the same game of chess, thus the answer to this riddle is simply that the two people are playing separate games that they individually won!

27. “There are three apples. You take two. How many apples do you now have?”

This is another delightfully deceptive riddle because it is worded in such a way that will make you think that it is some kind of math problem, but in fact, it is actually much simpler than that! All you need to consider is the wording of the riddle.

The riddle is asking how many apples you have, but the riddle has just told you that you have only taken two of the three apples that were lying around. This means that you now have two apples!

28. “What object can go up a chimney down, but cannot go down a chimney up?”

This is a riddle that really boggles the mind, and may prove to be one of the most difficult on this list. However, the resulting solution is very funny.

This riddle is particularly difficult because it sounds physically impossible. How can you possibly go down and up at the same time? However, if you think about what it is that is traveling up while it is ‘down’, then you may get closer to the solution.

The answer in this case refers to an ‘Umbrella’. An umbrella can either be ‘up’ or ‘down’. Thus, if the umbrella were ‘up’, it would no longer fit ‘down’ a chimney!

29. “What has no beginning, middle, or end?”

Again, this is another riddle that sounds far more complex than its resulting answer is! In this case, the riddle is referring to an object, and not a philosophical idea or question. The answer to this riddle is simply ‘a donut’.

Think about it, as a circular food, a donut does not have a distinct beginning, and thus lacks a distinct ending. It also does not have a center, giving it that iconic shape!

30. “What is made of water, but when put into water will disappear?”

This one should seem very obvious. It’s a very simple riddle, so it can make a good break from some of the more mind-boggling riddles we saw earlier.

The answer to this riddle is ‘Ice’, as it begins to melt when placed in lukewarm water!

31. “When I am young, I am tall, but when I am old, I am short. What am I?”

This one will get a teen’s mind thinking, as they will question how it is possible for something to get shorter as it gets older, especially as this is such a thing that does not happen to people as they age!

The answer to this question is ‘A candle’.which grows shorter the more it is used and melts away.

32. “How can a man go eight days without sleeping?”

This is another riddle that will have you deeply questioning the possibilities, but soon it comes to you. The key here is all in the wording. The riddle only mentions ‘Day’, thus it could be reasoned that the man in question simply only sleeps at night instead!

The answer sounds obvious when you hear it, but eludes many that hear the riddle!

33. “What has a bottom at the top?”

This is a very funny riddle that is sure to get a laugh from a teenager, thanks to its slightly more crude content. The solution to this riddle is ‘Your legs’. We will leave it to you to work out the joke here!

34. “What kind of room doesn’t have any doors or windows?”

You’d think that a room could not possibly exist without any windows or doors, so you could spend hours pondering this riddle. Luckily, all you need to consider is the word ‘Room’, and where else such a word belongs. The answer to this riddle is ‘Mushroom’, as mushrooms do not have windows or doors, but the word does have ‘Room’ in it!

35. “You are in a room with two candles. What do you light first?”

This is an incredibly misleading riddle that always generates a laugh when you reveal its solution. In this case, the riddle is inviting you to consider how exactly you would light either of the two candles. In most cases, you would use ‘a match’, which needs to be lit in order to light up a candle!

The riddle does not ask you which candle you light first, and simply what, of anything at all, you would light first!

36. “I am full of holes, but still I can hold water. What am I?”

Let’s close off this list with one of our favorite riddles. This riddle seems impossible, but it’s as simple as a ‘Sponge’!

To Wrap Up

These are just a few of the best riddles on the internet, but ones that are sure to get you closer to your own teenager.

Frequently Asked Questions

What can run but can’t walk?

The answer to this popular riddle is ‘A River’!

What Goes To Z To A?

This riddle refers to ‘Zebra’, which starts with ‘Z’, and ends with ‘A’.

What Flower Has 2 Lips?

This riddle is referring to the flower known as the ‘Tulip’!