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/Memory (21–30)
Which would you rather work at: a job with low pay but good relationships, or a job with high pay but terrible relationships?
When it comes to choosing a job, “salary” and “relationships” are often cited as key factors.
Ideally, both would be great, but this question asks what you prioritize when you can only have one.
Are you the type who can endure poor relationships for a higher salary, or would you rather live healthily in a good workplace environment even if the pay is low? It reveals each person’s approach to work.
Starting with extreme examples as an ultimate question and then discussing what balance feels ideal could make for an engaging conversation.
What would you do if zombies appeared?
Zombie movies and TV shows are always popular, but what would you do if zombies actually appeared? Even a far-fetched conversation topic like this might come in handy in an emergency! It might take a bit of courage to bring it up in everyday conversation, but it’s perfect for situations like a drinking party when the mood is a little elevated.
At gatherings, there’s almost always that moment when you run out of things to talk about.
At times like that, a wildly unexpected topic like this could be enough to keep the conversation lively.
What would you do if zombies showed up in Japan? Do you have a plan? Where would you run…? It might start off half-joking, but before long it could turn into a serious discussion! Give it a try for inspiration.
What’s the biggest hairstyle mistake you’ve ever made?
Hair grows even if you do nothing, and each time, everyone gets it cut with their own preferences in mind.
This question asks you to recall, among your experiences of getting your hair cut, what kind of hairstyle you felt was a failure.
Encourage them to clearly remember what ideal they were aiming for and how that led to the disappointing result.
It’s also recommended to expand the conversation into how that failure has been applied to their subsequent hairstyles and what their ideal hairstyle is going forward.
Love, Relationships, and Self-Introduction (1–10)
What hasn’t changed since you were little?
People grow as time passes from childhood, but there are surely parts of us that haven’t changed since long ago.
How about reflecting on those aspects that have remained the same since you were small and getting a feel for the path someone has walked? You could compare old photos with the present to find facial features that haven’t changed, or share episodes that reveal ways of thinking that have stayed consistent since childhood—there are many angles that could spark lively conversation.
By asking questions that prompt people to look back on their journey, they may come to truly sense what makes them who they are.
What are your past embarrassing moments or brag-worthy exploits?
Asking about memorable events from the path someone has walked is a question that lets you learn about the journey you didn’t know they’d taken.
Among those memories, how about focusing on especially striking moments—like embarrassing pasts or proud exploits—and asking about those? This question reveals what they consider good and bad, so it deepens your understanding not only of their stories but also of their way of thinking.
Unlike brag-worthy exploits, talking about one’s embarrassing past exposes their vulnerable side, so depending on what they choose to share, you can also sense how much they trust you.
When are you the happiest?
This question asks people to reflect on the moments in their daily lives when they feel happy, along with their everyday routines and emotions.
Through the question, you can also get a sense of what they value in life—such as fulfillment at work or in hobbies.
Because the theme is the simple happiness found in everyday life, it likely conveys how the person lives and reveals their character.
If you share the same feelings, you can enjoy an engaging conversation on common ground; if not, it’s a question that lets you discover something new.
Where do you draw the line for cheating?
In romantic relationships, cheating is arguably the quintessential unforgivable act.
However, where people start to consider something “cheating” varies widely, and those differing lines can sometimes lead to conflict.
Let’s make those boundaries around cheating the topic of conversation and learn about each person’s perspective.
Not only in terms of how one interacts with the opposite sex, but also in how quickly they close the distance with others, you can sense differences.
Stories about mishaps caused by differing views on cheating would likely liven up the discussion as well.
What kind of person are you bad with?
Everyone has things they’re not good with—not just ordinary things like certain foods, but also particular types of people.
This piece invites you to think about what kinds of people you find difficult and why.
By considering those types and your reasons, the deeper aspects of each person’s personality gradually come into view.
If you clearly share what you struggle with, you might receive advice on how to overcome it.
And if others empathize, it could even help build a sense of connection.
Do you believe in God?
This is a question that seems connected to each person’s religious views—whether they believe in the existence of God.
Not only specific faiths, but also experiences that can only be described as miraculous can be drawn out through this question.
The more someone has had seemingly miraculous experiences—chance encounters, brushes with death—the more likely they may be to believe in an invisible power.
It’s also recommended to expand the conversation beyond miracles to talk about what serves as a source of emotional support—something like a personal “god”—in their life.
What are the recommended local spots?
Everyone has lived in different places, and some may have grown deeply attached to where they’re from.
This question is one I’d especially like to ask people with a strong love for their hometown: where would you recommend locally? Whether they choose food or sightseeing spots, their picks might reveal what they value and how they lived.
Even within the same area, differing perspectives could lead to different recommendations.