A collection of hilarious questions that will liven up the conversation and might help you learn more about the other person
Spending time with friends asking “What if…?” questions can lead to unexpected discoveries and lots of laughs, right? But coming up with good questions is surprisingly hard.
Even when you rack your brain, they tend to end up sounding kind of generic.
In this article, we’ll share plenty of hilarious, high-energy what-if questions and prompts that help you reminisce together.
Depending on your answers, you might even strengthen your bonds.
If you want to make your conversations even more fun, be sure to check it out!
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What-if scenarios and reminiscences (1–10)
If you were to give yourself a nickname, what would it be?
I think it’s a common everyday scene to give someone a nickname and call them by it, with a sense of familiarity and ease of address.
This question asks: instead of giving a nickname to someone else, if you were to give one to yourself, what would you choose to be called? As a rule of nicknaming, people often use part of a name or base it on someone’s profile or behavior, so it also reveals how you view your own defining traits.
The sound of the name that makes you want to say it, the words you choose—various elements can convey a person’s sense of style.
Which historical figure do you think would make the world a better place if they were alive today?
As you can tell from looking through textbooks and the like, historical figures each accomplished great feats.
This question asks you to think about which historical figure, if they were alive today, seems likely to change the world.
Depending on your choice, we can get a sense not only of what aspects of history you like, but also which parts of the modern world that person might feel uneasy about.
It’s also a good idea to broaden the scope beyond Japanese history to include world history and test the person’s knowledge of history.
If you could go, which would you choose: the past or the future?
Time-slipping to the past or future is a classic theme in science fiction.
This question asks which you would choose if time travel were possible: the past or the future.
By limiting it to only one option, it encourages people to think carefully about where they truly want to go.
It also invites different perspectives—whether you simply want to see landscapes of a past or future you don’t know, or whether you have specific things you’d want to do in that era beyond just visiting.
What-if scenarios / Memories (11–20)
Which would you prefer: scorching heat all year round or extreme cold?
Summer’s heat can be harsh and winter’s cold can be severe, and perhaps the only reason we can endure them is because they alternate in turn.
This is the ultimate either-or question: if you had to face such extreme heat or cold all year long, which would be better? Rather than asking which is preferable, think by process of elimination—Which one could you still manage to endure? You can also use this question as a springboard to discuss strategies for dealing with heat and cold.
It’s a great way to segue into a conversation about how you usually cope with hot and cold weather.
What would you do if you won a large lottery prize?
This is a question that asks someone to come up with their ideal plan for how they would use a large lottery win if they were lucky enough to hit it.
You can get a sense of their attitude toward money based on what amount they consider a “big win” and how they would use it.
It’s recommended to have them think through both scenarios—spending it flamboyantly and building it up prudently—so you can see which approach they’re better at.
Focusing on whether they’d use it for themselves or also give back to the people around them could make it even more interesting.
If you were told you only had one week left to live, what would you want to do?
If you were told you only had one week left to live, what would you do? Some people might go see their loved ones, others might try things they’ve never done before, and some might prefer to spend time quietly alone.
Perhaps there are even those who would first think of their ongoing work.
If you ponder too long, you may end up wanting to do this and that, so if you want to know someone’s essence, it’s probably best to have them answer within a short time—say, a 10-second limit.
Which would you prefer: a long but ordinary life, or a short life that’s more fulfilling than anyone else’s?
It’s a question that makes you think about how you want to live your life.
Let’s pit two extremes against each other: wanting to live a long life even if it’s ordinary, versus wanting a rich, fulfilling life even if it’s short.
Do you wish for calm days or stimulating ones? You might learn about the differences in each person’s thinking.
It could also be interesting to exchange opinions and find each person’s point of compromise.
Another point to note is that the question includes vague terms like “longevity” and “a short life.” Discussing how many years each person imagines for those words would likely liven up the conversation.