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!
What-if scenarios and reminiscences (1–10)
If you could bring only one thing to a deserted island, what would you bring?
Everyone’s probably thought about it at least once: “If you could bring only one thing to a deserted island, what would it be?” If you answer seriously, you might say a lighter or a knife—something useful for survival.
Some people might choose ingredients, seasonings, or water.
But since it’s just a hypothetical, it’s also fun to go for a laugh.
For example, bringing money even though there are no stores, or bringing home appliances even though there’s no electricity.
Let your imagination run wild and enjoy it.
A similar topic is: “Who would you take with you to a deserted island?”
If you could only take one thing with you when evacuating during a disaster, what would it be?
Because disasters are hard to predict, it’s often said that it’s important to be prepared for emergencies.
This question asks what you would take with you if you encountered a disaster without any such preparations.
By limiting it to just one item, you can learn what someone considers indispensable in their daily life.
It also seems like a question that can reveal both practical items useful in a disaster and non-practical things they’d still want to keep close—shedding light on the path they’ve taken and what they cherish.
If you could enter the world of a movie or anime, which work would be good?
It’s a question that asks which movie or anime you’d like to enter if you could, and what you’d want to do there.
Through the question, you can not only learn which works are engraved on that person’s soul, but also sense how deeply they immerse themselves and empathize when they watch.
People may differ on whether they want to participate as a character or watch over the characters as a background extra.
Depending on the work’s atmosphere, you might also get a feel for what that person seeks in their everyday life.
If you could switch places with someone for a day, who would you want to be?
This is a question that asks you to think about who you would switch places with for a day and what you would do.
By focusing on experiencing a life different from your own, it reveals what kind of experiences you seek and what you admire.
How you act after switching is also an important point—whether you carry out that person’s usual activities or use their position for something different—and opinions are likely to split on that.
It’s the kind of prompt that conveys a person’s dreams of accomplishing things they can’t do themselves.
What’s the weirdest food you’ve ever eaten?
Stories about food are a classic crowd-pleaser.
Among them, the theme of weird foods always sparks episodes that make you laugh just by listening.
It’s fun to talk about why you tried a strange food and what you thought of it, and it gets even livelier when others chime in with playful jabs.
The speaker’s reactions are entertaining, listeners start recalling and sharing their own experiences, and the conversation never runs dry.
Whether it’s something famous abroad or a bizarre dish you tried for the first time recently, it’s a topic that both deepens your food knowledge and keeps the talk exciting.
If you had to choose a last supper, what would it be?
What would you choose for your last supper? Setting aside the idea that as we get older we can’t eat everything we want anymore—if you could eat absolutely anything you like, what would it be? A full-course meal at that upscale restaurant you’ve always wanted to try? Home cooking? Some people might even prefer sweets over a proper meal.
It’s fun because you might get some surprising answers depending on the person.
If you ask why they chose it along with their answer, you’ll get a clearer picture of what they feel and think.
If you could enhance just one of your five senses, which would you choose?
This question asks which of the five senses—those we rely on to live—you would choose to enhance.
Whether you pick vision, taste, or another sense conveys what you value in everyday life.
Your choice might also change depending on the degree of enhancement, so let’s think about which sense you’d like to use and how.
It could be fun to spin it into modest wishes too, like restoring diminished eyesight to normal or enjoying meals even more.