Situational riddles are those that involve some bizarre circumstances that have taken place. Your job is to account for or explain why the situation materialized in that particular way by challenging assumptions one commonly holds. The lowest hanging fruit in terms of solutions or reasoning almost never applies, so it’s up to you to deduce what’s really going on.

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The Man in the Bar
“A man walks into a bar and asks the bartender for a glass of water. The bartender then begins to search for something underneath the bar. Suddenly, he brings out a firearm and points it straight at the man. The man simply says, ‘Thank you,’ and immediately leaves.”
The question for the reader is, what happened?
Let’s attempt to completely clear our minds and look as closely as possible at this situation. By engaging in divergent (“opening up”) thinking, we can start to expand our ideas not only of what potentially happens in bars, but about glasses of water, and guns. We can then use induction and inference to tentatively make guesses about information we don’t yet have. There is clearly more to this story that we don’t yet see! But what could it be?
Let’s ask some questions to guide our thinking (many of which can be seen as clues):
- Why did the man ask for a glass of water at a bar (and not, say, some kind of alcohol)?
- Why did the man not give him what he wanted and instead threatened him with a gun?
- Finally, why did the man say thank you instead of protesting being threatened?
These questions lead us down the right path. The gun must have, in some way, been something the man wanted. So, what is the connection between a glass of water and a gun? Use creative thinking to imagine the state of mind that would have you ask for a glass of water—and also what set of conditions would have you saying thank you to having a gun pointed in your face. How would you feel if someone pointed a gun at you—and why would you thank someone for making you feel this way?
What at first seems like a strange situation is actually rich with clues. In asking the above questions, you slowly start to question your assumptions about certain situations. We all have fixed ideas of what guns and glasses of water mean. But what else can they mean?
If you’re ready to find out the answer, it follows: the man walking into the bar had hiccups, so he asked for a glass of water. Instead of giving him one, the bartender decided to scare away his hiccups with a gun instead. This worked, and the man leaves the bar, no longer needing his glass of water, and thanking the bartender for his help!
If you guessed the answer correctly, can you go back and see which questions helped you find it? Perhaps the insight came with imagining other creative and unconventional uses for water (not for thirst but to cure hiccups) and guns (not to threaten people but help them) or even fear (a good thing if it cures hiccups!). If you didn’t get the riddle, ask what exactly stopped you from seeing the “trick.”
Were you misdirected, or did you get stuck on only one possible explanation—for example, that having a gun drawn on you is always a bad thing? How could you avoid this trap in the future? You might decide to make a conscious effort to not assume what certain words, tools, ideas, or phrases mean. That in fact, much of their meaning derives from their context, and in solving problems of this nature, we have to carefully consider why a thing happens.
What starts out looking like a silly “gotcha!” riddle actually contains plenty of depth—it is only our fixed conceptual assumptions that limit us from seeing the potential in strange and unexpected situations. Remember that next time you are staring at a problem that seems completely incomprehensible!
Death in a Field
Feeling a little more warmed up? Let’s try another situational riddle. As you read it, try to remember what you learned from the last riddle, and approach this one with as open a mind as you can manage.
“A man is lying in an open field, dead. Next to him lies an unopened package. There isn’t another animal or person around him.”
The question is, how did the man die?
Again, we are faced with a strange situation, in this case, the end result of a process we can’t quite comprehend. Remembering what we learned from the previous example, we can perhaps start by assuming that things are not quite as they seem. Again, let’s try to ask “a more beautiful question” and see where our analytical thinking takes us.
There isn’t much information in the riddle, but we can start with the facts we are given. The riddle tells us no animal or other person is around, only an unopened package. It would seem that the package is connected to the man’s death, and not some other agent, like a human or animal killer.
- What do we know about packages and winding up dead?
- Can we think of ways of dying that can happen in an open field (maybe you think of a heart attack, stroke, or simply death from old age)?
- How many different kinds of packages can we think of (using divergent, creative thinking)?
What kinds of packages can result in a man’s death, or at least accompany it? (You might think of a packet of poison, but then—this one was unopened. The question is, then, what kind of package kills by not being open? You may lead yourself down the path of imagining the man was already sick and desperately needed to open a package that contained the cure, but was too late. But then, what kind of condition could he have that happens without any other people or animals present? Could the package contain insulin?).
What information are we really missing here?
More importantly, can we use what we understand about riddles in general to help us find the answer? So many riddles create a diversion, throw out a “red herring,” or deliberately obfuscate things. In what ways could this riddle be doing the same? In what ways are things being made to look more bizarre and unusual than they really are?
You might find yourself in the mindset of a detective who has to conduct very similar analyses of crime scenes, trying to piece together past events going only on clues left in the present.
If you’d like a clue, know that the man knew he was going to die just before he did.
If you’re ready for the answer, it follows: the man jumped from an airplane but hit the earth when his parachute didn’t open. It’s his parachute that is the unopened package next to him.
What can we learn from this little puzzle? As with the previous example, things are not what they seem. We solve this riddle by expanding our understanding of what a “package” could be, and thinking outside the box. In this case, there weren’t any animals or people around the man—but there was something in the sky. We might have heard “open field” and simply assumed this meant “the man is completely alone with nothing around him,” causing us to completely overlook the extra dimension of the sky above.
This is a tricky puzzle that’s possible to solve on your own—so long as you’re able to connect the unopened package with a death, and avoid the diversion of thinking the man died of an illness. How many different kinds of packages did you imagine, and can you see now that your imagination could have taken you even further?