Riddle Me This

Lately I’ve been into reading and writing riddles.

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Yes, I said riddles. (Don’t act so surprised; you already know I’m a “word nerd”!)

While researching riddles on Reddit, to my surprise and delight, I found some that relate to Halloween. Below are my favorites.

In case you’d like to try your hand at solving them, I’ve placed the answers waaay down at the bottom of this post (below the gif of Frank Gorshin, who played the Riddler on TV back in the 60s). Feel free to let me know how many you got correct in the comments!

1. The Black Cat

A black cat stepped out onto a black road, where there were no streetlights and not even the faintest glimmer of light from the moon. A black car approached with its lights turned off, and yet the driver slowed down and allowed the cat to cross the road. How did he know the cat was there?

2. Password

A man wants to go to a haunted house, but he does not know the password required for entry. The man observes other people being let in as they talk to the haunt’s security guard. The guard says “Twelve”; the first visitor says “Six” and gets admitted. Another visitor appears, and the guard says “Six”; the visitor then says “Three” and is allowed in too.

The man now understands the pattern, and he goes up to the entrance. The guard says “Ten,” and quickly the man says “Five.” But then the man is rudely turned away by the guard. Why?

3. Drawing Blood

I am an injury you inflict upon yourself, but not on purpose. I make your skin bleed and sting, but without the use of a knife or scissors. In fact, you can get me just by reading. What am I?

4. What’s Inside

I am inside you, but you didn’t eat me. I cannot stand up on my own, but I will outlast you. What am I?

5. Mass Murder

A man is the only man living in his building. Nobody lives around him for miles. One night, he goes up to his room, turns off the light, and goes to sleep. The next morning, he learns that without leaving his building, he has killed 39 people overnight. How?

6. The Container

Fill me with water; fill me with land.

Fill me with anything; hold me in your hand.

But be wary, and hear my cry–

For the day you boot me, you shall surely die. What am I?

7. Gargoyles

You stand in front of two large, ancient doors. One is the entrance to Heaven, and the other is the entrance to Hell. Each door is guarded by a terrifying gargoyle. You have been told that you may ask one gargoyle one question, but one of the gargoyles always lies, and the other always tells the truth. What is the one question you would ask to determine which door goes to Heaven?

Riddles from this Reddit page; I’ve rephrased a few of them.



1. It was daytime.

2. The password is based on the number of letters in the word the security guard says (e.g., the word “Twelve” has six letters in it, etc.).

3. A paper cut.

4. A skeleton.

5. He lives in a lighthouse. He turned off the light and caused a ship to crash, killing 39 people.

6. A bucket.

7. This one’s difficult. You would ask one of the gargoyles which door the other gargoyle would say leads to Heaven. Both gargoyles would indicate the same door, which is the door to Hell. You’d wisely choose the other one. (Read a more-detailed explanation here.)

2 responses to “Riddle Me This”

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