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 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.
Until what age did you believe in Santa Claus?
For children, Santa Claus is the greatest joy of Christmas, and many probably fell asleep looking forward to their presents.
This question lets us see how each of us grew up by exploring what we believed about who Santa really is.
Until when did you truly think Santa was secretly coming? What shattered that illusion, and what were the episodes that led to it? Let’s reflect on those personal stories as well.
And since there may still be people who believe, it’s best to be gentle and avoid spoiling their dreams.
What was the most interesting thing during your school days?
If you’re looking for an open-ended topic, “What was the most interesting thing you experienced during your school days?” works well.
Have everyone share their own interesting anecdotes.
“Interesting” can mean many things—something fun, a mistake you can laugh about now, a hobby you were really into, and so on—so there are lots of ways to expand the conversation.
Talking about the past reveals personality and interests, helping people grow closer.
Try this when you’re struggling to find a common topic.
Romance, human relationships, and self-introduction (11–20)
What anime or manga did you like when you were a child?
Guaranteed to get everyone excited.
It’s about the anime and manga you loved as a kid.
This will likely vary a lot by generation.
Start by each naming your favorite titles and see if there’s any overlap.
If you liked the same works, the conversation will probably take off even more.
It’s also fun to chat energetically about which scenes you love and which characters are your favorites.
As a twist, you could also bring up favorite TV dramas or trends from back then.
What’s a song you always sing at karaoke?NEW!
If you’re a music lover, here’s a question you should definitely try asking: have them guess your go-to karaoke song.
If it’s someone you’ve been to karaoke with many times, they might get it right.
Otherwise, they’ll likely have to deduce it from your generation and musical tastes.
What makes this question tricky is that the songs you usually listen to aren’t necessarily the ones you sing.
Even younger people sometimes have a surprising Showa-era classic as their signature number.
If you’ve got an unexpected go-to song like that, try asking this question and surprise everyone.
