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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Love, Relationships, and Self-Introduction (1–10)
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.
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.
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 was your childhood dream?
Didn’t everyone have something they wanted to be when they were a kid? Here’s a suggestion: ask, “What was your childhood dream?” Depending on the era, it might have been an anime character or a popular profession.
Or it could have been something you wanted to do, like “I want to travel around the world” or “I want to live in a castle.” I hope it brings out your inner child and gets everyone excited.
Many people’s dreams changed as they grew older, so it might be good to first decide what age you’re talking about and ask with that in mind.
