[Talk] Interesting! Hilarious! A Collection of Silly Questions
Haven’t you ever had a blast with “silly questions” born from a bit of curiosity? From everyday doubts you toss around with friends to outlandish “what if” scenarios, those questions that make you stop and think are surprisingly fun, aren’t they? In this article, we’ll introduce silly questions that can bring people closer together.
Even though they’re simple, they make you think more deeply than you’d expect—why not try answering them yourself? There are no right answers.
That’s exactly why it’s so enjoyable to share everyone’s opinions!
- A collection of questions that will liven up conversations with friends. Talk themes to deepen your bond.
- A collection of fun questions with the theme “What if 〇〇?”
- [Talk Theme] Liven up the drinking party! A roundup of funny questions
- A collection of hilarious questions that will liven up the conversation and might help you learn more about the other person
- With friends or couples! A set of questions perfect for penalty games
- Fun two-player games recommended that you can play using conversation only
- [Ultimate Either-Or] A great conversation starter and a chance to get to know each other!
- A collection of questions to liven up phone calls with someone you like or are interested in
- A collection of personality quizzes perfect for killing time
- [Personality Test] Fun and Entertaining! Carefully Selected Tests That Everyone Can Enjoy Together
- [Easy] Punishments that will get middle schoolers excited
- [Lovey-Dovey] Couple’s Challenge! Question Game Roundup
- [Classic] Funny! Hilarious! A roundup of punishment games that will liven up the classroom
Ultimate Choices (11–20)
Which would you prefer as a boss: someone you can get along with but who isn’t good at their job, or someone with a bad personality but who is competent?
I always look forward to Meiji Yasuda Life’s annual “Ideal Boss Rankings Chosen by New Employees.” In 2024, the top man was Teruyoshi Uchimura from the comedy duo Ucchan Nanchan, and the top woman was announcer Asami Miura.
Both give off a bright and dependable image.
Seeing names like Kawashima from the manzai duo Kirin, actor Muro Tsuyoshi, and Mikio Date from Sandwichman ranking highly among the men makes me think everyone really does long for a fun workplace.
What do you think?
Which is better: a job that’s too busy or a job that’s too quiet?
One good thing about being busy at work is that time passes quickly—or at least it feels like it does.
A job where you just stand in a desert-like place watching to see if any intruders come… I’m not sure such a job actually exists, but if it did, it would probably feel extremely boring.
And when you’re bored, time doesn’t pass, does it? Busy jobs require physical stamina, and you have to be mentally tough, too.
Thinking about it that way, a moderately busy job is best for both body and mind!
If you could buy it with money, which would you choose: health or time?

Even if you’re healthy, if you’re so busy that you can’t do anything you want, you’ll end up under considerable stress.
And even if you have money, if you don’t have the time to use it, you can’t help but wonder what the money is for.
Conversely, no matter how much time you have, if you’re not healthy, nothing you do will feel enjoyable.
When you’re hospitalized, you have plenty of time, but it’s not all that fun, is it? Time has meaning precisely because it’s limited, and health has meaning precisely because we take care of our bodies.
It’s a profoundly thoughtful question.
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.
If you had to date someone who’s careless with either money or time, which would you choose?
This is a question that makes you think about what kind of major flaws in a partner you could forgive.
Because being careless with money or time are shortcomings that directly affect daily life, you can also get a sense of what each person values in their day-to-day living.
Try to clearly imagine what life would be like with each type of careless person, and consider how you’d feel and how it would impact your life.
Some might say that “being careless” depends on the degree, so discussing the thresholds of what you can tolerate could make for an engaging conversation.
If it had to be either summer all year round or winter all year round, which would you choose?
This is a question asking which you would prefer if the entire year had to be either hot summer or cold winter.
Answers would likely vary not only based on the simple preference of liking summer or winter, but also on whether you handle heat or cold better.
Beyond differences in comfort, there are foods and activities that can only be enjoyed in each season, so some people might focus on those.
It’s a question that could also reveal how people spend each season and what they look forward to.
Which would you dislike more: if everyone else disappeared from the world except you, or if you were the only one to disappear from the world?
This question asks which you would dislike more: being the only one left in the world, or being the only one to disappear from it.
If you vividly imagine both scenes—living alone in a world with no one else, and a world where you have vanished and everyone else carries on as usual—you’ll likely sense which feeling of discomfort is stronger.
Thinking about what would be difficult if you were alone can also prompt you to reflect on how you and others are connected in everyday life.
If opinions arise such as not being able to accept that people live happily in a world without you, the differences in viewpoints could become clear and make for an engaging discussion.



