More Complex Riddles

Analytical riddles are more challenging than situational ones because instead of shifting perspectives, they require you to carefully analyze information to arrive at conclusions. This is the classic comparison of divergent versus convergent thinking. It might be easier depending on your proclivities, but often, the devil is in the details.

Five men are walking together when it starts to rain. Four of them start walking quickly, while the fifth doesn’t. Yet he stays dry, and the other four get wet. They all arrive at their destination at the same time. How?

A window cleaner is cleaning windows on the twenty-fifth floor of a skyscraper when he slips and falls, yet isn’t harmed despite not wearing any safety equipment. How?

Questions or comments regarding the podcast?

As you’ve seen, the kind of riddle we explored in part one could be solved by switching perspective, questioning ordinary assumptions, and looking more closely at words, tools, or situations to find a hidden, overlooked aspect where the solution lies. These riddles are sometimes solved quickly in a flash of insight—you may or may not get them, but if you’re stuck, it seldom makes it better to keep thinking.

Our next group of riddles, however, requires a little more than a quick shift in perspective or a flash of insight. Instead, these riddles are all about carefully picking your way through details to arrive at a logical conclusion.

The Riddle of Five Men

The riddle goes like this: “Five men are walking together. It starts to rain, and so four of the men speed up and walk more quickly; the fifth man doesn’t try to pick up pace—yet he stays dry. The other four men, however, get wet despite trying to avoid it. The five men all arrive together at their destination at the same time.”

Immediately, you can tell that this puzzle will require a different set of intellectual tools than our previous riddles. Let’s put away the lateral and creative thinking and instead bring out the analytical thinking. Remember the important aspects of this way of thinking: first identification, then research, some inference, deduction or induction, determining relevance, and finally, curiosity.

Let’s begin by identifying the problem. It seems on the surface impossible that four men should get wet while the other doesn’t, despite them seemingly moving more or less together. The puzzle seems to be: what is different about the fifth man or what he is doing that results in him not getting wet when the others did?

There are many details to this puzzle, all of which need to be considered separately, then combined. The man makes no effort to stay dry and yet does. The men arrive together. A hint might help you narrow down the possible answers that might work here: not all of the men were on foot.

A possible scenario: the fifth man was in a car or other kind of vehicle, so he was shielded from the rain. However, this is a little weird—it would entail the men walking closely beside a slowly driving car. Bodyguards surrounding an important figure in a ceremonial car, for example? Another option is that the fifth man is ill somehow and lying down on a stretcher, being carried by the other four men. However, this would still result in the fifth man getting wet. Unless . . .

As you can see, another solution is possible. Here it is: The man is actually dead and being carried by the other four, who are the funeral’s pallbearers. They run and get wet anyway, but the dead man doesn’t because he is covered inside the coffin.

To arrive at this answer, you likely had to systematically work your way through possible solutions and decide whether they worked or not. Doing so brought you closer and closer to the answer, not so much by flash of insight but by methodical and logical steps. We can see this kind of thinking in real life all the time. Doctors do it when they perform differential diagnosis: “It can’t be this, it can’t be that, so that means it must be the third thing.” You’ll recognize this process as a form of deductive reasoning.

Riddles like this teach us to use conditionals in our thinking, or IF, THEN, AND, or BUT operators. We think along the lines of, “If the man was with the other four all along and didn’t get wet, then he must have been covered somehow, or inside something else . . .” These are processes that we take for granted until a riddle like this shows us how important they are in problem solving!

The Murderer’s Choice

Our second analytical riddle asks you to carefully consider a few options and then make your choice between them using whatever data you can. Here it is: “A murderer is found guilty and condemned to death in a rather cruel and unusual way. He is instructed to choose to open one of three possible doors. Behind the first is a room full of powerful raging fires; behind the second is a room full of deadly assassins with weapons, hellbent on killing him; in the third is a room with vicious lions who haven’t eaten in years.”

The question is, which room would be the safest for the murderer to choose if he wanted the best chance of survival?

Okay, thinking caps on. We’ll need to use our analytical minds to unpick the relative risks associated with each choice. This parallels a lot of critical thinking tasks we all have to do in real life—choosing between different careers, different houses or areas to live in, even different romantic partners. How are we even going to start weighing up the risks of each room?

To start with, the raging fires seem pretty grim—would it really be possible to survive being burned alive? The second room doesn’t look good either—one highly trained assassin could probably finish you off, not to mention a whole room full of them. Similarly, a room full of hungry lions could quickly make a meal of the man. Which would be the best choice?

If you’re eagle-eyed or familiar with riddles, you may have easily spied the answer already. The truth is that the riddle only seems like a complex analytical puzzle on the surface—in reality, it’s very, very simple. It’s as though we are primed to see three choices and then immediately begin weighing them up (not to mention this book is deliberately misleading you as well . . . sorry about that!). Have you spotted the obvious clue that makes all this analysis unnecessary?

The answer to the riddle follows: the third room is the safest, because all the lions would be dead, since they “haven’t eaten in years.” If you’re groaning and rolling your eyes now, it’s probably because you were caught out by what you thought the riddle was asking, rather than looking very clearly at what it was actually saying.

There is a similar riddle that asks a person a series of complex mathematical questions to do with age, and finishes with the question, so how old are you? The answer is to simply say how old you are—the rest of the riddle was nothing more than an elaborate red herring.

It’s worth looking closely at admittedly annoying riddles such as this one. Sometimes ordinary life really does appear to us as more complex than it really is. Being used to solving things in a particular way, we race ahead and solve it using the method we think we’re being asked to use, completely missing the obvious and simple answer staring us in the face.

The person thinks he is facing a multiple-choice question where he is meant to sum up the relative risks (and to be fair, the riddle sets him up in this way). In other words, people only think they know what is being presented: three very dangerous rooms. What this riddle also does is play with conceptual frames. The person hearing it might assume that “haven’t eaten in years” is simply a figure of speech or an exaggeration for effect. Tackling riddles like this teaches us something both profound and simple: read the instructions thoroughly!