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Brain Teasers and Riddles 

With Multiple-Meaning Words

happy boy

Brain teasers and riddles are a great way to practice language skills. If students can see the humor in word play, it shows they have a good understanding of word meanings.

To solve these riddles, you’ll need to use words that have more than one meaning. For example, a story can mean a legend or news account, or it can mean the level of a building. The first joke uses this word.

Multiple-Meaning Mania!

Brain Teasers and Answers from www.spelling-words-well.com

Printable Brain Teasers 


man climbing up a stack of giant books

1. How can you make a library bigger?

2. What kind of instruments do all animals have inside of them?

3. When do bad days usually fall apart?

4. When do kids get the most exercise?

5. What cannot run although it has three feet?

blue music notes

6. Why was the music teacher so upset?

7. If a man gives fifteen cents to one of his sons, and a dime to another, what time is it?

8. What’s the quickest way to make a point in your writing?

9. What is the fruit of history?

10. Where were the first donuts fried?

artist's palette

11. When do artists paint the best oceans?

12. What’s a prisoner’s favorite punctuation mark?

13. What never asks questions but is often answered?

14. What animals are well-educated?


15. Who is a sound sleeper?

16. What did the mountain say to the earthquake?

17. What do gingerbread men put on their beds?

18. Where do you find the biggest spiders?

brown dog with tongue hanging out

19. How do you make an egg roll?

20. How do dog catchers get paid?

Check your answers with ours.

More Brain Teasers and Riddles

brain with turning gears

You might also enjoy our brain teaser riddles that use homophones.

Why not try some of these assortments of fun brain teaser questions? Each one is also available in printable form.

In addition to our brain teasers and riddles, your students might also enjoy our  Mystery Words  puzzlers and Picture Puzzler worksheet pages.

NEW! - Fun Brain Teasers for Students  These fun brain teasers will check your students' spelling and vocabulary skills. They’ll also tickle their funny bones! 

More Difficult Brain Teasers

If you're looking for more challenging brain teasers and word play puzzlers, take a look at these:

man with lots of luggage

Travel Teaser - One of our most difficult logic brain teasers. Can you figure out who went where and when?  

Hidden Words - Put your logic skills to the test on this entertaining word brain teaser. How long will it take you to discover three hidden words?

detective with large magnifying glass

Brain Teasers for Adults  & Upper Grade Students - Two REALLY difficult letters with hidden messages. Good spelling skills are the key to uncovering them!

Don't miss our wide assortment of spelling worksheets. and spelling word games.  We have lots of fun, educational activities for all ages and abilities!


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