For overconfident adults and teens

Tricky Riddles

A tricky riddle works by letting you make an assumption. A plumber and an electrician stand in line, one is the father of the other's son, and the mind goes looking for a complicated family tree. A plant that turns out cars sounds like nonsense until you stop picturing something green. The answer was available the whole time; you just read the words the usual way.

The difference between tricky and unfair is that the real answer has to be clearly right once it is revealed. We avoided riddles that only work by bending a word past its normal meaning, or that hide a clue nobody could reasonably spot. If the room groans and says "of course", the riddle did its job. If the room argues, it didn't, and it isn't here.

30 riddles ✓ Every answer tested blind
Print as cards

How to play tricky riddles at a table

These work best read aloud, once, without repeating. Tricky riddles rely on the listener filling in a picture quickly, and a second reading gives people time to question it. Let everyone write a guess on paper before anyone speaks, then reveal all the guesses together. A whole row of identical wrong answers is the payoff.

To score it, give a point for the right answer and take one away from anyone who fell for the obvious reading, so a careful player can win by guessing less.

Tips for not getting caught

  • Underline every word that could be read two ways, such as plant, kid or hand, and try the less common meaning first.
  • Question who the riddle assumes the people are; several of these traps depend on the listener picturing a particular kind of person.
  • If an answer feels impossible, check whether the riddle actually says what you think it says, word for word.
  • When you are the reader, keep a straight face and don't stress any key word, or you'll give the trick away.
Page 1 of the Tricky Riddles printable card pack: eight cut-out cards

Print these as cards

All 30 on 4 pages of cut-out cards, eight to a page, with the answers on a separate sheet so nobody peeks. Prints on US Letter or A4.

Download the PDFAll riddle card packs

How this page was checked

Every riddle here went to a second solver without its answer. When they reached a different answer that also fit, the riddle was rewritten and tested again, or cut. Our editorial standards.

Drafted for this page
40
Solved blind
30
Cut as repeats of other pages
10
Original to this site
21

More to try