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44 Pencil Riddles

Pencils are more than just writing tools; they can also be a source of fun and mental exercise as well! 

Pencil riddles combine the everyday object with the challenge of solving brain-teasers. 

Get ready to sharpen your wits as we explore some delightful riddles that will keep you entertained and engaged.

Pencil Riddles

  1. Why did the pencil draw a broken line?

  2. How does a pencil introduce itself in a party?

  3. What’s a pencil’s favorite mode of transportation?

  4. Why was the pencil always calm?

  5. Why did the pencil fail its math test?

  6. What did one pencil say to the other during a race?

  7. Why couldn’t the broken pencil win the argument?

  8. How do pencils apologize?

  9. Why was the pencil so good at history?

  10. What do you call a pencil with two erasers?

  11. Why did the pencil go on vacation?

  12. What makes a pencil unique at a party?

  13. How does a pencil feel when it’s sharpened?

  14. Why don’t pencils make good detectives?

  15. What did the paper say to the pencil?

  16. Why did the pencil draw stairs?

  17. What do you call a pencil’s best friends?

  18. Why did the pencil cross the road?

  19. What happens when a pencil takes a vacation?

  20. Why are pencils poor?

  21. What’s a pencil’s favorite subject in school?

  22. Why don’t pencils tell secrets?

  23. What did the pencil sharpener say to the pencil?

  24. Why was the pencil so small?

  25. What did the paper do when it met the pencil?

  26. How do you know if a pencil is good at math?

  27. Why was the pencil always tired?

  28. Why did the pencil go to school?

  29. What do you call a pencil that doesn’t work?

  30. What did the pencil say to the other pencil?

  31. Why do pencils always seem to understand you?

  32. What did the pencil say to the sharpener?

  33. Why was the pencil so good at explaining things?

  34. How did the pencil feel about winning an award?

  35. Why did the pencil go to bed?

  36. What did the pencil say after making a mistake?

  37. Why did the pencil look different?

  38. What happens when a pencil breaks in two?

  39. Why was the pencil so popular?

  40. How does a pencil stay in shape?

  41. Why was the pencil’s story so confusing?

  42. What did the eraser say to the pencil?

  43. Why did the pencil keep getting lost?

  44. What did the math book say to the pencil?


  1. Because it couldn’t draw a straight line.

  2. “Hello, I’m write on time!”

  3. The “lead” car.

  4. Because it always had a point to stay composed.

  5. Because it couldn’t decide which point to stick to.

  6. “Look sharp, we’re drawing to a close!”

  7. It couldn’t make its point.

  8. By erasing their mistakes.

  9. Because it could go back to any period.

  10. Pointless.

  11. To get a little break.

  12. It’s always the highlight.

  13. A little sharp, but quite on point.

  14. They always lead you on.

  15. “Write on!”

  16. Because it wanted to draw a step up.

  17. Eraser and paper – they always stick together.

  18. To get to the other side of the stationery shop.

  19. It gets a little break!

  20. Because it’s always a little sketchy with money.

  21. Drawing.

  22. Because they’re always worried about being erased.

  23. Stop going in circles and get to the point!

  24. Because it was a little short on lead.

  25. It felt quite torn about the encounter.

  26. It always has a point.

  27. Because it worked overtime on the drawing board.

  28. To improve its skills in draw-matics.

  29. Non-sense-sical.

  30. You’re looking sharp today!

  31. Because they’re always on point.

  32. You’re really sharp today!

  33. It always had a fine point.

  34. It was beside itself, write on cloud nine.

  35. Because it was drawn out.

  36. This is not the end; I can still be turned around.

  37. It was feeling a bit dull.

  38. You get a couple of pointless pieces.

  39. Because it was part of the in-crowd (ink crowd).

  40. By doing daily circular motions.

  41. Its plot was all over the place.

  42. You always bring out the best in me.

  43. It kept going down the wrong paths.

  44. Stop going in circles and get to the point!
pencil riddles

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