These riddles were selected by none other than Greylock’s own Mr. Thistle, a veritable master of lateral thought.

The Man in the Bar

A man walks into a bar and asks the bartender for a glass of water. The bartender pulls out a gun and points it at the man. The man says ‘Thank you’ and walks out.  Why?

Answer: The man had hiccups. The bartender recognized this from his speech and drew the gun in order to give him a shock. It worked and cured the hiccups – so the man no longer needed the water.

Push that Car

A man pushed his car. He stopped when he reached a hotel at which point he knew he was bankrupt. Why?

Answer: He was playing Monopoly.

Car Wreck

A man and his son are in a car wreck on the highway.  The father, unfortunately, dies.  The son is air lifted to the hospital.  The doctor enters the room, prepared to do surgery.  When the doctor looks down at the boy, the doctor says, ‘I can’t operate on this boy, he is my son’.  How is this possible?

Answer: The doctor was his mother.