Recommended for kids! A collection of challenging riddles. Difficult questions that make you think.
“Huh! That was the answer?” Ready to try some brain-teasing riddles that might make you blurt that out? If your child finds ordinary riddles too easy, the ones introduced here will have them firing on all cylinders and having fun! In this article, we’ve gathered challenging riddles that really test flexible thinking and imagination—perfect for kids to tackle.
There are plenty that kids can solve smoothly while adults end up going “hmm…” But if you think them through together as a family, you’re sure to find new discoveries and spark fun conversations.
Come on—let’s dive together into the world of riddles that stimulate intellectual curiosity!
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Recommended for kids! A collection of hard riddles. Challenging brain teasers (31–40)
What are the two things a younger brother has but a younger sister has only one of?
See the answer
The hiragana “to”
The word otōto (younger brother) contains two instances of the syllable “to,” while imōto (younger sister) contains only one. Both are family terms, but in this riddle the key is not their meanings—it’s the letters within the words. If you look closely at the words and consider which characters appear and how many times, you’ll arrive at the answer.
[Advanced Riddles] A set of 14 tough questions!
![[Advanced Riddles] A set of 14 tough questions!](https://i.ytimg.com/vi/-Q9M6GuAuXk/sddefault.jpg)
These riddles are packed with tough questions that require clever thinking.
They’re difficult for beginners, but confident kids should definitely give them a try.
The intense, ominous background music will make you feel as if you’re facing a boss battle in a video game.
Riddles for adults
These are high-difficulty riddles where you discover the answer by combining flashes of inspiration with the knowledge you’ve accumulated so far.
You’ll be tested on flexible thinking—like spotting trick elements in the question text or finding words that can be rephrased.
Some answers even involve kanji, so how broad your knowledge is also plays a key role in the challenge.
If you rewrite the problem entirely in hiragana or try reading it out loud, you might find it easier to notice the hint words.
15 difficult riddles
Here are 15 difficult riddles.
They’re very challenging, so there may be very few people who can get them all right.
Try to think flexibly.
Some of the words that appear in the questions and answers are a bit more adult-oriented, so we encourage not only children but also adults to take on the challenge together.
What gets smaller the bigger it gets?
The bigger it gets, the smaller it becomes… What does that even mean? you might wonder.
“Getting bigger” and “getting smaller” are opposites, and something that gets bigger doesn’t become smaller.
What we need to consider when solving this riddle is how to interpret “bigger.” In this puzzle, “bigger” means “growing.” When you grow, isn’t there something that becomes smaller? You probably experience it often when the seasons change.
The answer is clothes! As your body grows and gets bigger, the clothes you wore last year become too small and no longer fit.