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Very Hard Riddles

Very hard riddles can either be fun or frustrating, depending upon the situation. Either way, they often capture our attention and often hold onto it until we finally find an answer. Below are some resources for finding very hard riddles, as well as a brief history of how these difficult brainteasers began.

Humor from the Ancients

Very Hard Riddles

We all love to laugh, enjoy other’s company and spend some time pondering things nonsensical. Humor is essential to the heart. This emotional need for a balance between work and play is exactly why difficult riddles date back to early civilizations.

Archeologists have even found ancient sacred temples with carved puzzles and mind benders, although they were very different from the type with which we are familiar. Today's "modern" brainteaser dates to the Middle Ages; this is when street entertainers made their living by challenging their audiences with very hard riddles. The base format of a riddle -- asking a question and challenging a response -- helped to truly engage the audience and make these entertainers popular as they traveled through towns.

What started as a great entertainment venture for early creative artists is now wonderful entertainment for us. Very hard riddles can help to pass the time on a leisurely afternoon, some good-naturedly tormenting us for hours as we search for the solutions. While your administering riddler may go easy on you and give you the answer to an exceptionally challenging puzzle, history shows that earlier people groups were much more ruthless.

The Ancient Greeks loved riddles, especially difficult ones. They were used as a means of proving intellectual superiority, and winners even sometimes received laurel crowns as a status symbol for their quick wit. Very hard riddles were also used in Africa as a rite of passage for young people. If they failed to answer them, they could not be officially recognized as adults. Riddle tournaments have even allegedly reached the remotest islands of Fiji, where the champions enjoyed a grand feast.

Today, some groups of friends and family continue to tease and jab each other in the same ways early tribes and villages did, and we also sometimes tend to gloat and elevate our social status via riddle solving, just as it was done in the ancient past. In short, we haven’t really changed at all.

Finding Very Difficult Riddles

Finding a tough riddle can be tricky, as it often seems the same ones circulate through both conversation and e-mail forwards. To find a truly difficult brainteaser, you’ll have to hunt. A great place to start online is, which features plenty of tortuous riddles for those who love a good stumper. The site also rates each riddle on a 5-star scale, so you can quickly find the most challenging and entertaining selections. is a site you will never tire of, as they update their homepage with a new riddle each and every day. Keep up with the daily mind bender and explore their archives to find a hard riddle that will take your favorite riddler plenty of time to solve.

Lastly, will provide you with some riddles that will greatly challenge you, as well as provide some simpler puzzles for when you need a quick break from your daily responsibilities.

Looking for a challenge for kids? Ultimate I Spy contains plenty of riddles that will be challenging for kids aged 7-10. Manufactured for the Nintendo Wii system, you can start their love of very hard riddles early on by encouraging them to push through when the game stumps them. Watch their minds and curiosity grow with this newest form of riddle solving.

Classic Hard Riddles

While these classics may not seem hard to those who already know the answers, they have stumped generations of people. Do you know the solutions?

1. You have a jug of milk, and you need to measure out just one cup. How do you do this if you only have a three-cup measuring container and a five-cup container?

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Fill the 3-cup container with milk and then pour all three cups of milk into the 5-cup container. Fill the 3-cup container with milk again and then use it to fill the 5-cup container the rest of the way. The remainder left in the 3 cup container will equal one cup.

2. What gets wetter and wetter the more it dries?

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by Tamara Warta