If you’re into riddles, here are some doozies — but don’t feel bad if some or all of them stump you, because people throughout history have struggled, too!

Just have fun with them, and wipe your brow when you come out the other side.

Riddle #6. Gollum’s Trick

“Voiceless it cries,
Wingless flutters,
Toothless bites,
Mouthless mutters.”

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Answer for #6.

The wind.

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Riddle #5. The Mad Hatter’s most maddening question.

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Alice never guesses the answer to his question “Why is a raven like a writing desk?” Can you?

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Answer for #5

Well, the Hatter (and Carroll) didn’t have a good answer, at least not until this appeared in the preface of a later edition of the book:

“Enquiries have been so often addressed to me, as to whether any answer to the Hatter’s Riddle can be imagined, that I may as well put on record here what seems to me to be a fairly appropriate answer, viz: ‘Because it can produce a few notes, tho they are very flat; and it is never put with the wrong end in front!’ This, however, is merely an afterthought; the Riddle, as originally invented, had no answer at all.”

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Riddle #4. Follow in Oedipus’s footsteps?

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Sophocles asks Oedipus, “What walks on four feet in the morning, two in the afternoon and three at night?” Our hero (antihero?) nails it, but can you?

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Answer for #4

“Man: as an infant, he crawls on all fours; as an adult, he walks on two legs and; in old age, he uses a ‘walking’ stick.”

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Riddle #3. Solving this puzzle doesn’t requite witchcraft.

Image Credit: Warner Bros.

But it does come from the 4th Harry Potter book, The Goblet of Fire. Harry is tasked with solving it during the Triwizard Tournament. Can you figure it out, too?

“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?”

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Answer for #3

A spider.

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Riddle #2. The One That Started Everything

There is debate over who wrote the first riddle. Ancient civilization of Sumer wrote one of them. Sumerians’ contribution to the legacy of logic problems:

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

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Answer for #2

Answer: A school

Riddle #1. Raymond Smullyan’s Heaven and Hell

This riddle, created by mathematician Raymond Smullyan, has gone by many names: “A Fork in the Road,” “Heaven and Hell,” and “The Two Doors,” but they all go something like this:

“You’re met with a choice between two identical doors with an identical guard at each. One door leads to heaven and one door leads to hell. You can ask one guard one question and then make your choice on which door to pass through. One of the guards always tells the truth and one of them always lies. So, what question do you ask?”

You might recognize it from the 1986 movie “Labryrinth,” in which Jennifer Connelly’s character answers correctly. What does she ask and why?

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Answer for #1

Sarah answers like this:

She asks the one on the left, “Would he [referencing the guard on the right] tell me that this door leads to the castle?” He tells Sarah ‘yes,’ and from there she concludes that he is the one guarding the door to “certain death.”

There are endless resources on the internet regarding this riddle if you want a deeper dive!

Got a fun riddle you want to share?

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