Seven Riddles from the Town with Two Barbers (2024)

  1. You've just arrived in a new town, seeking your fortune, and you need a haircut. In this town, there are two barbers. The first barber has a neat, dapper haircut, and his shop is immaculately clean. The second barber's haircut is grotesque, and his shop is filthy—giant tumbleweeds of hair drift across the floor, and the scissors are caked in layers of rust. Which barber do you want to cut your hair?

Answer: You cleverly deduce that the first, well-groomed barber couldn't possibly cut his own hair; therefore, he must get his hair cut by the second barber. And, though the second barbershop is filthy, it's because the second barber has so many customers that there's simply no time to clean. Thus, you correctly decide to patronize the second barbershop.

  1. You worked up an appetite trying to settle on a barbershop. In this town, there are two sandwich shops. The first sandwich shop is spick and span, with floors thatyou could eat off of. The owner is a jolly fat man. The second shop is filthy, with piles of rancid bologna on the floor, pepperoncini in the toilet, and Swiss cheese jammed into broken light fixtures. The owner is emaciated and covered in sores. Where do you get your sandwich?

Answer: You should obviously get lunch from the clean sandwich shop. Never buy food from a place with such glaring health-code violations! You don't have to be good at riddles to know that; it's just common sense. Unfortunately, you choose to get a sandwich from the second shop. You have assumed that the rules that applied to the town's barbershops would apply to its delis as well. Why would you think that? A guy who makes sandwiches can easily eat his own sandwiches.

  1. You ate a bad sandwich and are feeling sick. In this town, there are two doctors. The first doctor's patients are the very picture of health, and his waiting room has an excellent magazine selection. The second doctor chain-smokes and refuses to wash his hands, and in his waiting room there's only a waterlogged Sports Illustrated from 1995—not that you'd be able to read it anyway; the dying patients packed in there wail so loudly that it's impossible to concentrate on anything. Which doctor do you decide to see?

Answer: Trick question! The town used to have two doctors, but now it has only one. The first doctor died due to complications from a runny nose while under the care of the second doctor. The second doctor gives you some pills he found in an ashtray and tells you to get a good night's sleep.

  1. Following the bad doctor's orders, you decide to rent a hotel room for the night. In this town, there are two hotels. One has a pool. The other has room service. Which hotel do you stay at?

Answer: You're too sick to swim, so you decide to stay in the hotel with room service and to order some saltines and ginger ale. Unfortunately, you have picked the bad hotel. "Room service" is a euphemism for when the concierge sneaks into your room in the middle of the night and beats you with a sock filled with loose change.

  1. You fear that between the beating, the weird ashtray pills, and the food poisoning, you don't have long to live. In this town, there are two priests. One is a regular priest. The other stabs his parishioners. Which one do you want to administer your last rites?
Seven Riddles from the Town with Two Barbers (2024)
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