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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Romance, human relationships, and self-introduction (11–20)
Do you think I’m an angel or a devil?
Everyone carries both good and evil in their hearts, and we make choices each day as that balance shifts.
These questions are meant to help you consider which way your heart currently leans—whether your angelic or devilish side is stronger.
Reflect on your past good deeds and misdeeds, and think about which is more dominant, taking into account not only your own view but also the opinions of those around you.
If you judge that your devilish side is too strong, it’s also recommended to use that insight to improve your future behavior.
What heart-fluttering moments have you experienced so far?
Conversations about romance really get people fired up, don’t they? Here’s a topic I recommend: “What heart-fluttering moment have you experienced?” Share a story that made your heart skip a beat and make your listeners swoon, too.
Most people will probably think of romantic moments, but it’s also great to talk about times you were charmed by an animal or touched by someone’s kindness.
Tell everyone your top pick of a heartwarming episode—your personality will come through even more.
Which celebrity have you been told you look like?
Hasn’t everyone been told at least once, “You look like so-and-so”? It’s a little flattering when the comparison is to someone cool or cute, isn’t it? Still, many people might find it hard to answer when asked this question.
Celebrities are exceptional in some way, so it can feel presumptuous to declare that you resemble one.
But that’s exactly why your sense of judgment is put to the test.
You can name someone you truly resemble and win their agreement, or deliberately pick someone totally different and get a laugh!
What was the tastiest restaurant you’ve been to recently?
A person’s usual range of activities and their food preferences aren’t something you can tell at a glance.
That’s why it’s worth adding this question.
While it’s about recommending places to eat, it opens up the conversation with prompts like “Did you go there on a trip?” or “What was the most delicious?” If you’ve been to the recommended place, you might share similar tastes, which makes it feel like you could really hit it off—how nice is that? Some people aren’t big on eating out, so in that case, have them answer with places other than restaurants.
What are the local specialties?
If you’re asking questions in a gathering with people from various regions, it might be fun to ask about local specialties.
Everyone probably knows the famous ones, but sharing items that only locals would know could spark interest and help the conversation flow.
It’s also a good idea to add a bit of extra info—like tasty ways to enjoy the specialty or well-known shops that carry it.
It’s a lovely question that lets you take an interest in the region and the person who grew up there through their local specialties.
In conclusion
Did you enjoy exploring a world of “what ifs” through those fun questions? Sometimes honest answers lead to unexpected discoveries.
And by digging into your memories, you might have rediscovered stories that make you burst out laughing.
Let’s keep chatting and nurture an even deeper bond together!