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Tough Riddles

Do you like to try your hand at tough riddles? There are all kinds of riddles, like math riddles, logic riddles, and riddles that ask a question, like, "What am I". Following are some examples of tough riddles and links to online sites for more.


A riddle is a statement or question that requires a lot of thought to answer. Sometimes it is something you have to figure out or it has a play on words that makes it tricky. Synonyms include: conundrum, puzzle, brainteaser, enigma, dilemma, twister, mind-boggler, stumper, teaser, quandary, predicament, perplexity, and charade.

Here are a couple of tough riddles that have been around a while. Is this statement a lie or the truth: "Everything I tell you is a lie." If it were telling the truth, then the statement would not be true, so it is contradicting itself. Therefore, it must be a lie. Next, "If your sock drawer has four blue socks, two red socks, eight black socks, and six brown socks, what is the least number of socks you would have to pull out in the dark to be sure you had a matching pair?" The answer to this one is five, because there are four colors, so if you first four draws were one of each color, the fifth draw would match one of them.

Different Kinds of Riddles

Here are some examples of hard riddles grouped by type from Tricky Riddles. They are grouped by: logic, math, and what am I? What is it? Who am I? words and letters, and miscellaneous.


Question: Jackie's mom has 7 kids. They are Maddie, Madeleine, Madison, Magdalena, Marion, and Monica. What is the 7th child's name?
Answer: Jackie

Question: There were two girls born in the same hospital that looked exactly the same and were born into the same family. However, they were born in different years. How is that possible?
Answer: They were born on New Year's Eve and New Year's Day.


Question: I am a three-digit number. My tens digit is five more than my ones digit. My hundreds digit is eight less than my tens digit. What number am I?
Answer: 194

Question: How do you add eight 8's to get 1,000? (Using addition)
Answer: 888+88+8+8+8 = 1,000

What Am I?

Question: What remains dark when all else is light?
Answer: A shadow.

Question: I have seas without water, forests without wood, deserts without sand, and houses without bricks. What am I?
Answer: A map.

What Is It?

Question: The person who builds it doesn't want it. The person who buys it doesn't need it either. The person who uses it doesn't even know he is. What is it?
Answer: A coffin.

Who Am I?

Question: I am not my sister, I am not my brother, but I am still the child of my mother and father. Who am I?
Answer: I am myself.

Words And Letters

Question: How do you make 7 even?
Answer: Drop the S.

Question: What starts with an E ends with an E and has 1 letter in it?
Answer: An envelope.


Question: A horse is tied to a rope five meters long. There is a barn filled with hay 6 meters away yet the horse can get up and eat the hay whenever he wants. How can that be?
Answer: The rope is only tied to the horse and is not tied to anything else.

Here are a few more from Increase Brain Power

Question: 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?
Answer: 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.

Question: If it has a quart capacity, how many pennies can you put into an empty piggy bank?
Answer: Only one, because after that it won't be empty.

Question: What is broken every time it is spoken?
Answer: Silence.