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Difficult Riddles

Are you looking for some difficult riddles with answers to pass the time and keep that brain sharp? Riddles are fun for all ages, and research has even shown that people who play riddle games have better memories as they age. If you have mastered all of the easy riddles, enjoy this collection of more challenging riddles. How many can you solve?


Difficult Riddles with Answers

Are you ready to flex your brainpower? Try your hand at solving these riddles, inspired by the riddle set from Increase Brainpower. You can find the answers below.


  1. You need to measure one gallon of oil out of a barrel, but you only have a three-gallon container and a five-gallon container. How do you do it?
  2. Every time it is spoken, this is broken.
  3. A man married three women in Michigan. He never got divorced and none of his wives died, yet he didn’t break the law. How did he do it?
  4. Before a judge handed down a sentence, he let the convicted person make a statement. The judge said that if the statement was true, he would only sentence the convicted to four years in prison. If the convicted made a false statement, the sentence would be six years in prison. The convicted made the sentence, and the judge let the person go free. What was the statement?
  5. You have a piggy bank that has a capacity of one gallon. When it is empty, how many nickels can you put into it?
  6. In a family, there is a mom, dad and four sisters. Each sister has one brother. How many people are in the family?
  7. In your drawer, there are six white socks, eight black socks, four tan socks and two brown socks. Without looking at the socks, how many do you have to reach in and pull out to end up with a matching pair?
  8. What work can no one ever finish?
  9. There are three cups of flour and you take one away. How many cups of flour do you have now?
  10. You can take four of the five letters out of this word, but the pronunciation never changes. What is the word?


  1. Start by filling the three-gallon container. Dump those three gallons into the five-gallon container. Refill the three-gallon container and pour as much of the contents as you can into the five-gallon container. That should leave one gallon of oil in the three-gallon container.
  2. Silence
  3. He works as a Justice of the Peace.
  4. The convicted said the sentence would be six years in prison. If that statement were true, then the judge would have to give him four years in prison – which would then make the statement false. In order for the statement to be false, the judge could only sentence him to four years in prison, which would make the judge have to go back on his word. The convicted got to go free because it was the only way the judge could stick to his word.
  5. You can only put one nickel in. After you have put that nickel in, the piggy bank won’t be empty anymore.
  6. There are seven total people in the family – the two parents, the four sisters and the one brother.
  7. You need to take out five socks. There are four colors of socks, so if you take out five, you are sure to have two of the same color.
  8. Their autobiography
  9. You only have one cup – you took it away.
  10. Queue (remove the last four letters – the pronunciation is the same)

More Riddles and Answers

Still craving more difficult riddles with answers? Give the following websites a try:

Heather McDonald