Medium difficulty riddles sit in the sweet spot: challenging enough to make you think, but not so hard that you give up. These require a bit more lateral thinking, wordplay awareness, or logical deduction than easy riddles. They are ideal for group problem-solving sessions, date nights, or whenever you want a satisfying mental challenge.
188 medium riddles
A man was found dead next to a 13 story building. The police say it was a suicide, but you say it was a homicide (someone killed him). To prove this, you go to...

I am never quite what I appear to be. Straight-forward I seem, but it's only skin deep, for mystery most often lies beneath my simple speech. Sharpen your wits,...

Almost everyone sees me without noticing me, For what is beyond is what he or she seeks. What am I?

It's hard to give up. Remove part of it and you still have a bit. Remove another part, but bit is still there. Remove another and it remains. What is it?

A natural state, I'm sought by all. Go without me, and you shall fall. In times past you'd me when you spend, and use me when you eat to no end. What am I?

A young man walks through the forest. He comes to a bridge. In front of the bridge is a large man carrying an axe. The man says, "If you want to cross this brid...
Alex was the strongest man in the world. He can lift up something that weighs 1000 kg easily. He can even pick up five women at once without any pain. But one d...

At your wedding, you are introduced to your new partner's mother's only sister's husband's sister in law. What do you call this woman?

A merchant can place 8 large boxes or 10 small boxes into a carton for shipping. In one shipment, he sent a total of 96 boxes. If there are more large boxes tha...

A man was found dead in his study. He was slumped over his desk and a gun was in his hand. There was a cassette recorder on his desk. When the police entered th...

Dean Sam and Castiel are three brothers. Interestingly their current age is prime. What's more interesting that difference between their ages is also prime. H...

One brick is one kilogram and half a brick heavy. What is the weight of one brick?

2 men and a boy started a never ending race. One of the men can run super fast while the other man can run way faster than the boy. The boy is the slowest runne...

You bought a cute little girl mouse at the pet store. This mouse can breed once every month, 7 babies at a time. So how many mice will you own in exactly twelve...

What is a word made up of 4 letters, yet is also made up of 3. Sometimes is written with 9 letters, and then with 4. Rarely consists of 6, and never is written...
A man murders his wife with a knife in their car. Nobody is around to see this. He throws her out of the car being careful not to leave any fingerprints on her...

What is the largest possible number you can write using only 2 numbers - just 2 numbers, no other mathematical symbols?
What is the value of 1/2 of 2/3 of 3/4 of 4/5 of 5/6 of 6/7 of 7/8 of 8/9 of 9/10 of 1000?

Cathy has six pairs of black gloves and six pairs of brown gloves in her drawer. In complete darkness, how many gloves must she take from the drawer in order t...

A man leaves home. He goes a little ways and turns a corner. He goes a while and turns another corner. Soon, he turns one more corner. As he's returning home, h...

You're in a room with no windows and no doors. All that's in there is a table and a mirror. How do you get out?

A certain crime is punishable if attempted but not punishable if committed.

In the land of the green glass door there are riddles but no answers, sheets but no blankets, and books but no words. Name something found in the land of the gr...

Where can one stand up straight, but still be considered sideways?