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Hard to Answer Riddles

Hard to answer riddles have been around for ages and during the 16th and 17th centuries contests for answering riddles abounded. If you enjoy finding, reading, and attempting to answer riddles, check out some of the sites below for riddles that are hard to answer. Then, find out what's needed to create your own riddle that is hard to answer.


Most riddles are a play on words. That way, only one answer is correct and it may not seem obvious to the person trying to solve the riddle. Other riddles could be regional, meaning the answer to the riddle is a local person or someone whose name fits the play on words in the riddle. Even other riddles have obvious answers but because we tend to look too hard for an answer, you may not get the correct answer right away. As you can see, riddle answers can be almost anything the creator wants it to be, you just have to think a little deeper for the harder riddles.

Where to Find Hard to Answer Riddles

  • At Increase Brain Power you can start your riddle quest with 23 hard to answer riddles. Some are short form—meaning they are a simple question—and others are mathematically-related. A few are longer, giving you a description in paragraph form with as many clues as necessary. The answers are located at the bottom of the page, but try to answer them all before you move there.
  • Another site to stoke your intelligence is Most of these are moderately hard, especially for children and teens. There are 15 riddles with answers. Also on the same site are Hard Riddles with Answers. You'll find hard riddles for adults as well as children on this page. The answers are available if you click the "Show Answer" link.
  • With over 8,000 riddles, Think Riddles will keep you busy for a long time. Many of the riddles are user submitted, so you may find ones you've heard before or original ones that will keep you stumped. As you browse the site, you'll see themed riddles like math or Halloween and riddle collections for children, teens, and adults. Not sure where to start? The main page has four daily riddles to get you started.
  • Tricky Riddles organizes their riddles in categories like Logic, Math, What am I, What is it, Who am I, Words and Letters, and Miscellaneous. Some of the riddles are added from the owners of the website, but you can suggest a riddle of your own or one you've heard as well as rate others' riddles. The database of riddles is large at this site so it should keep you busy for weeks. However, if you don't have that kind of time, you can opt to receive the daily riddle in your e-mail.

Make Your Own Riddle

So how do you make your own riddle? Riddlemakers have different techniques, but one of the easier ways is to start with an answer. Next, think how you can play around with words that describe your answer. For example, if you wanted to write a riddle about socks, then you have to think of everything related to socks: they go on feet, they keep your toes warm, and they cover the soles of your feet. Now if you spoke this riddle, it may go something like "What covers your sole, keeps you warm, and is always two feet wide?" The answer? Socks, of course. The trick is when you say "sole" people may think "soul" and forget about the rest of the clues.

Brain Teasers

Hard to answer riddles are a great way to get your mind sparked for the day. Receive a newsletter or a daily text with a riddle so you can start the day with an exercised mind.