Brain Teasers and Riddles
with Multiple-Meaning Words 

Boy laughing at brain teasers and riddlesBrain 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!

Printable Brain teasers and Riddles


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?

6. Why was the music teacher so upset?

7. If a man gives fifteen cents to one of his sons, and a time 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?

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?

19. How do you make an egg roll?

20. How do dog catchers get paid?

Check your answers.

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. Don't miss our wide assortment of spelling worksheets. We have pages for all ages and abilities!

Go to main page for Free Brain Teasers 

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