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 / Memories (11–20)
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.
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.
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.
If you could be invisible for just one day, what would you do?NEW!
Psychic powers are a staple element in stories, and many people have probably imagined abilities they admire.
Among such powers, let’s focus on the ability to become invisible and try to predict what someone would want to do with it.
It could be exciting to consider this not only from the questioner’s personality but also to see how close it is to what the respondent wants to do.
You could also segue into topics like other possible uses, making it a fun conversation starter as well.
What is something you absolutely can’t do but would like to try?NEW!
“Conquer every country in the world,” “Live with 100 kitties,” “Spend 100 million yen in a single day”—many of us have probably thought about things we’d love to try even if they’re hard to achieve, right? Here’s an idea: turn those ambitions into a quiz.
People who know your usual hobbies, favorites, and personality might even guess your secret dreams.
After enjoying the quiz, have everyone share their own ambitions too—it’s sure to liven things up even more.
Do you want to be immortal or not?
Immortality refers to a state in which one neither ages nor dies, but would you want to be immortal, or not? People have long said that immortality is a human dream, but there’s also the saying that life is beautiful precisely because it is finite.
When I think about how, even if I were immortal, my loved ones would eventually pass away when their time comes, it feels a bit lonely.
That said, perhaps those who wish to be immortal harbor a corresponding level of ambition in their hearts…
It’s a question that makes you want to dig deeper into the reasons behind your answer.
What subject did you like when you were a child?NEW!
Different people tend to have different strengths and weaknesses in the various subjects they studied at school.
This activity asks you to guess which subjects someone was good at and which ones they liked, so you can sense differences in their personalities.
Since being good at a subject doesn’t always match liking it, the prediction can be tricky when there’s a gap.
Using that as a starting point, it’s also a great idea to shift the conversation to topics about the subjects themselves—like what aspects they enjoyed.
It might be a chance to look back on the time when you were learning.
Which work would you like to see a sequel of?
Among the many works that exist in the world, each of us has pieces that are etched in our hearts—and some of those are the ones whose sequels we can’t help but wonder about.
How about sharing the works for which you especially long for a sequel, and reflecting on what you love about them? There are many forms this anticipation can take: stories that reached a happy ending but make you want to see what lies beyond, or ones that were cut off mid-story.
You could also branch out from the theme of “works you want a sequel to” and consider the flip side: works that might actually be better without a sequel.
If you were to enter a karaoke singing contest, what would you sing?
Even if you’ve had chances to sing at karaoke and the like, few people have experience performing in front of an audience.
This is a question about what you would sing if you had the opportunity to showcase your singing in front of an audience—say, by entering a singing contest.
Would you choose something you’re used to singing, or a song that more people know? Let’s think about selecting songs that fit the occasion.
It also sounds fun for everyone to imagine how the crowd would react and how hyped the performance would get.