[Difficult] Riddles for High School Students
When you hear “riddles,” you might strongly associate them with kindergarteners or elementary school kids, but some are challenging even for adults.
This time, we’re introducing a collection of difficult riddles aimed at high school students.
Give them a try when you have some spare time!
- [Easy] Riddles for High School Students
- Funny quizzes and riddles that get everyone excited in high school
- [Challenging and Fun!] Quizzes & Riddles for Adults
- Easy Quiz for High School Students
- [Hard] Riddles for junior high school students
- Riddles for college students. Questions that test thinking and creativity.
- Recommended for kids! A collection of challenging riddles. Difficult questions that make you think.
- [Battle of Wits] Stimulate your intellectual curiosity! Quiz questions that get adults excited
- [Satisfying When Solved] Challenging Quizzes Recommended for Elementary School Students!
- [Brain Training] Difficult Riddles That Even Adults Struggle With
- [Easy] Fun and Educational Quizzes! A Collection of Interesting Problems for University Students
- Funny quizzes for middle school students. Quizzes that can liven up a middle school setting.
- A quiz site for university students, featuring everything from academic to entertainment quizzes!
[Challenging] Riddles for High School Students (21–30)
A quiz that 99% of people get caught by

It’s hard to arrive at the answer! Here are some ideas for quizzes that trick 99% of people.
These are riddles that most people get caught by, and to find the answer, it’s important to approach them with flexible thinking.
Try looking at them from different angles with your friends and family.
For example, there’s a question like: “You picked up a wallet someone dropped.
What should you do with the wallet you picked up?” Try thinking with an open mind!
Riddle Battle: College Students vs. Middle Schoolers

This is a video where a college student and a middle school student take on riddles in a battle format.
The difficulty is set so that even a middle schooler can solve them, but the people in the video answer quickly.
If you try not to lose and think along with them, it requires quick reflexes and might make it even more enjoyable.
Genie of the Lamp AI

Did you know that the genie of the lamp is clever? On top of that, this video features a showdown between a genie equipped with artificial intelligence and a highly intelligent human.
In this video, the University of Tokyo Quiz King provides the answers.
Can you answer using your own knowledge and experience? Give it a try!
Five brain-training riddle questions

This is a collection of five riddles, each accompanied by clear, helpful illustrations to spark ideas along with the problem statements.
Even if you’re unsure, there are easy-to-understand explanations with the answers, so why not try this brain-training challenge in your spare time? It might be perfect for a bit of mental exercise.
Insanely difficult riddle

As the title suggests, this is quite a difficult riddle.
Solving it requires both riddle-solving knowledge and vocabulary, so it can’t be solved by someone who is only good at riddles or someone who is confident only in their vocabulary.


