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Six Tricky Riddles that Will Leave you Thinking

by Julia Chaly '24


They're fun, they're puzzling, they take time, they're the mind's loose nail! Here are some of some famous perplexing riddles and why they can be so tricky...

  • Sophocles: The Sphinx’s Riddle

“What goes on four legs in the morning, on two legs at noon, and on three legs in the evening?”


Oedipus the King, written in ancient Greece during the fifth century BC, is the famous tragedy containing this brilliant brain teaser. In this devastating story, Oedipus fulfills his destiny while trying to avoid it. Oedipus faces the Sphinx, a being with the head of a woman and the body of a lion. The Sphinx stands at the gates of the city of Thebes, puzzling travelers with this riddle. If a traveler solves the riddle, they can enter the city intact. If they guess incorrectly, they become the Sphinx’s next meal. Can you guess the answer? “What goes on four legs in the morning, two legs at noon, and three legs in the evening?” A human! When they are babies, humans crawl on hands and knees, hence the “four legs.” Humans walk on two legs in mid-life, which represents “noon,” and use a walking stick (“three legs”) in old age (“the evening”).

  • Eighteenth-Century England: A Riddle with a Vengeance

“As I was going to St. Ives,

I met a man with seven wives,

Each wife had seven sacks,

Each sack had seven cats,

Each cat had seven kits:

Kits, cats, sacks, and wives,

How many were there going to St. Ives?”


This riddle originated as an old nursery rhyme in the seventeenth century. Even though a 1730 manuscript first documented this riddle, it is famous for appearing in the Die Hard threequel, Die Hard with a Vengeance. The villain asks Bruce Willis and Samuel L. Jackson to solve the riddle in 30 seconds to save civilians from a ticking bomb. The answer, you might ask? One. Yes, the answer is only one person. This riddle is a trick question. It throws in all of those sevens in there to make you think you have to complete calculations. In reality, the speaker was traveling to St. Ives when he met everyone. So to say, no specific details state the destinations of all the other characters.

  • Ancient Sumer: The World’s Oldest Riddle

“There is a house. One enters it blind and comes out seeing. What is it?”


In Sumer, located in present-day Iraq, this riddle intended to test the brain’s “worth.” Can you guess what kind of “house” the speaker is referring to? A school! The Sumerians emphasized the value of education and knowledge. When children begin their education, they can be considered “blind” in that they are ignorant and innocent. However, as they learn, they become more aware and thoughtful. They are no longer “blind” and “come out seeing.”

  • The Hobbit: Gollum’s Final Riddle

“This thing all things devours;

Birds, beasts, trees, flowers;

Gnaws iron, bites steel;

Grinds hard stones to meal;

Slays king, ruins town,

And beats mountain down.”


In this popular series, originally written in 1937, Bilbo Baggins, the Hobbit, finds himself having to riddle-solve for his life to escape from the underground lair of the evil Gollum. Gollum tells Bilbo he will grant him a safe passage through if he solves five riddles, the last of which is this one. What do you think is the “thing” in this riddle? The answer? Time. Bilbo, who solves every other riddle correctly except for this one, is just lucky. In asking Gollum to give him more seconds to solve the puzzle, he blurts out the word “time” and wins his freedom.

  • Harry Potter and the Goblet of Fire: The other Sphinx’s riddle

“First think of the person who lives in disguise,

Who deals in secrets and tells naught but lies.

Next, tell me what’s always the last thing to mend,

The middle of middle and end of the end?

And finally give me the sound often heard

During the search for a hard-to-find word.

Now string them together, and answer me this,

Which creature would you be unwilling to kiss?”


In the 4th Harry Potter book, Harry participates in the Triwizard Tournament, a dangerous magical competition. During the final task, he traverses through an obstacle-filled maze. One of the obstacles involves a Sphinx who won’t let Harry pass until he solves her riddle. The answer to this tongue-tying riddle? A spider.

This riddle has three parts. The “liar in disguise” is a spy. The middle of “middle” and the end of “end” refers to the letter D. And finally, “er” is the sound referenced in the third part of the clue. Once you guess these three mini-clues, the riddle becomes a puzzle, and you have to put the three parts together to form the answer: “spy-d-er.” Harry successfully solves the first and third parts, then puts them together and guesses the creature must be a spider. The Sphinx lets him pass. Later on, Harry fights a giant spider in the same maze, learning that the riddle was also a warning.

  • Riddle: Match Game

“You measure my life in hours, and I serve you by expiring. I’m quick when I’m thin and slow when I’m fat. The wind is my enemy.”


Hard riddles want to trip you up, and this one works by hitting you with details from every angle! No one knows where this riddle originated; however, it has been confusing people for decades! Can you guess the answer? That’s right, a candle. Many overthink this riddle, render it too easy, and miss the key detail—or question. What does wind threaten most? You have to stretch your brain to come up with something tiny and unexpected!

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