Riddle #1: Tricky Riddles
Riddle #2: Still Tricky
Riddle #3: Hard Ones
Riddle #4: Creepy Ones
Riddle #5: Grab Bag
100

Mr. Taylor has four daughters and each has a brother. In total, how many children does Mr. Taylor have?

Five children because all of his daughters have the same brother.

100

How can you throw a ball as hard as you can only to have it come back to you without it bouncing off of anything?

 Throw the ball straight into the air.

100

Which English word is the odd one out: Stun, Ton, Evil, Letter, Mood, Bad, Strap, Snap, and Straw?

Letter as it is the only one that does not spell another word when it’s written backward.

100

A young woman is attending her mother's funeral. While there, she meets a man she has never seen before and falls in love immediately. After the funeral, she tries to find him but cannot. Several days later she kills her sister. Why does she kill her sister?

She killed her sister hoping to see this man at her sister's funeral.

100

There was a plane crash every single person died. Who survived?

Married couples.

200

I possess a halo of water, walls of stone, and a tongue of wood. Long I have stood; what am I?

Castle.

200

 I am the beginning of the end of time and space that surrounds everything and every place. What am I?

The letter “E”.

200

Which word has three consecutive double letters?

Bookkeeper.

200

When you have me more, you can see only less. What Am I?

Darkness.

200

The more these are taken, the more they are left behind. What are they?

Footsteps.

300

What can run but never walk, have a mouth but never talk, have a head that never weeps, and a bed that never sleeps?

 A river.

300

 A man attending his mother’s funeral sees a woman in another pew, and experiences love at first sight. He tries to find her but has no luck. A few weeks later, he kills his sister. Why does he kill his sister?

He kills his sister in hopes of seeing the woman at her funeral.

300

I am born tall and grow short with age. What could I be?

 A pencil.

300

Imagine you are in a sinking rowboat surrounded by sharks. How would you survive?

Quit imagining.

300

Two girls ate dinner together. They both ordered iced tea. One girl drank them very fast and had finished five in the time it took the other to drink just one. The girl who drank one died while the other survived. All of the drinks were poisoned. How is that possible?


The poison was in the ice.

400

 If an electric train is moving north at 55 mph and the winds blowing east at 70 mph, which way does the smoke blow?

An electric train doesn’t emit smoke.

400

 People in poverty have this. If you eat this you will die. What is it?

Nothing.

400

The person who makes it and the person who buys it have no use for it and the person who uses it never sees it or feels it. What is it?

Coffin.

400

A man was found dead with a cassette recorder in one hand and a gun in the other. When the police came in, they immediately pressed the play button on the cassette. He said "I have nothing else to live for. I can't go on," then the sound of a gunshot. After listening to the cassette tape, the police knew that it was not a suicide, but a homicide. How did they know?

If the man shot himself while he was recording, how did he rewind the cassette tape?

400

I eat to live and drink to die. What could I be?

 Fire.

500

How many letters are in the alphabet?

Eleven letters are in “the alphabet”.

500

A is the brother of B. B is the brother of C. C is the father of D. How is D related to A?

 A is D’s aunt.

500

My buddies and I were inseparable mates until one by one we were split. My teacher then gave me a smack on the head so off in the corner I sit. What am I?

A staple.

500

A man is found murdered on a Sunday morning. His wife calls the police, who question the wife and the staff, and are given the following alibis: the wife says she was sleeping, the butler was cleaning the closet, the gardener was picking vegetables, the maid was getting the mail, and the cook was preparing breakfast. Immediately, the police arrest the murderer. Who did it and how did the police know?

The maid. There is no mail on Sundays.

500

A wealthy man lives alone in a small cottage. Being partially handicapped, he had everything delivered to his cottage. The mailman was delivering a letter one Thursday when he noticed that the front door was ajar. Through the opening, he could see the man's body lying in a pool of dried blood. When a police officer arrived he surveyed the scene. On the porch were two bottles of warm milk, Monday's newspaper, a catalog, flyers, and unopened mail. The police officer suspects it was foul play. Who does he suspect and why?

The police officer suspects the newspaper delivery person. The absence of Tuesday's and Wednesday's newspapers indicates that the delivery person knew there was no one there to read it.