Our Hard Riddles Collection
The following collection includes some really difficult riddles,
and some not-so-hard riddles as well (just to keep readers from
getting too frustrated). The answers for almost all of them are
at the bottom of the page. Almost, I say, because I am engaging
in a bit of riddle-cruelty, and leaving you to ponder one of
them without an answer. Enjoy!
The More Difficult Riddles
1. What row of numbers comes next in this series?
2. A man was to be sentenced, and the judge told him, "You
may make a statement. If it is true, I'll sentence you to four
years in prison. If it is false, I'll sentence you to six years
in prison." After the man made his statement, the judge
decided to let him go free. What did the man say?
3. You have a barrel of oil, and you need to measure out just
one gallon. How do you do this if you only have a three-gallon
container and a five-gallon container?
4. If your sock drawer has 6 black socks, 4 brown socks, 8
white socks, and 2 tan socks, how many socks would you have to
pull out in the dark to be sure you had a matching pair?
5. What is broken every time it's spoken?
6. How did Mark legally marry three women in Michigan, without
divorcing any of them, becoming legally separated, or any of
7. Mom and Dad have four daughters, and each daughter has
one brother. How many people are in the family?
8. What English word retains the same pronunciation, even
after you take away four of its five letters?
9. If I say "Everything I tell you is a lie," am
I telling you the truth or a lie?
10. What work can a painter never quite finish?
11. Why wasn't Bertha put in jail after killing dozens of
12. Why wasn't John able to take a photo of his mother with
13. If there are three cups of sugar and you take one away,
how many do you have?
14. What has a mouth but can't chew?
15. How many letters are in the alphabet?
16. What gets wetter and wetter the more it dries?
17. What can travel around the world while staying in a corner?
18. Food can help me survive, but water will kill me. What
19. Take away the whole and some still remains. What is it?
20. What stinks when living and smells good when dead?
21. When is it bad luck to meet a white cat?
22. If it has a quart capacity, how many pennies can you put
into a empty piggy bank?
One More Hard Riddle
23. Which of the following statements are true?
1. At least one of these ten statements is false.
2. At least two of these ten statements are false.
3. At least three of these ten statements are false.
4. At least four of these ten statements are false.
5. At least five of these ten statements are false.
6. At least six of these ten statements are false.
7. At least seven of these ten statements are false.
8. At least eight of these ten statements are false.
9. At least nine of these ten statements are false.
10. At least ten of these ten statements are false.
1. 1113213211 After the first line, each line describes the
previous line: One One, Two Ones, One Two, One One (and so on...).
2. He said, "You'll sentence me to six years in prison."
If it was true, then the judge would have to make it false by
sentencing him to four years. If it was false, then he would
have to give him six years, which would make it true. Rather
than contradict his own word, the judge set the man free.
3. Fill the 3-gallon container with oil and pour it into the
5-gallon container. Then fill the 3-gallon container again and
use it to fill the 5-gallon container the rest of the way. One
gallon will be left in the 3-gallon container.
4. Five. There are only four colors, so five socks guarantee
that two will be the same color.
6. It's part of his job - he's a justice of the peace.
7. Seven. The four daughters have only one brother, making
five children, plus mom and dad.
9. A lie. It can't be the truth without contradicting itself
(and therefore being a lie), but some of my statements can be
lies, and this is one of those statements.
10. Her autobiography.
11. She was a hurricane.
12. You can't use curlers to take photos! You need a camera.
13. You have just one - the one you took away.
14. A river.
15. There are eleven letters in "the alphabet."
16. A towel.
17. A stamp.
19. The word "wholesome."
21. When you're a mouse.
22. Just one - after that it won't be empty.
23. You're on your own on this one, but don't worry. It isn't
the most difficult of these riddles.
I reserve some of the toughest riddles for the Brainpower
Newsletter, which is sent out by email every Sunday morning.
If you are not already a subscriber you can sign up (no charge)
using the form on the home page or in the side panel to the left.