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Categories: questions

150 interesting questions: what to ask for an engaging conversation

Interesting questions are the “bomb” in every gathering. Because who doesn’t enjoy a good conversation?

But questions like “what do you do?” and “where do you live?” are so cliche, boring, and exhausting to answer.

However, a “good” question can be the difference between a long and predictable night and a great, and fruitful meeting of the minds.

So, if you want to be the most interesting person in the room, you’ve got to ask the most engaging questions that will result in captivating conversations.

The following 149 interesting questions will help you go beyond small talk and foster new friendships.

Interesting questions that are personal

Tell me the 3 best things about you.
On a scale of 1-10, how strict are/were your parents?
Who was your worst teacher? Why?
Who was your favorite teacher? Why?
Which would you pick: being world-class attractive, a genius or famous for doing something great?
Who are the 3 greatest living musicians?
If you could change one thing about yourself, what would it be?

What was your favorite toy growing up?
Name 3 celebrities you most admire.
Name a celebrity you think is lame.
What accomplishment are you most proud of?
Which of your friends are you proudest of? Why?
What’s the most beautiful place you’ve ever been?
What are your 3 favorite movies?
How would you describe me to your friends?
Which historical figure would you like to be?

What’s the right age to get married?
Tell me 3 things you remember about kindergarten.
What paper that you’ve written are you most proud of?
What would you do if you were invisible for a day?
Who would you like to live like for a day?
If you could time travel, where would you go?
If you could live in any TV home, what would it be?

What’s your favorite ice cream flavor?
Would you rather live for a week in the past or the future?
What’s your most embarrassing childhood memory?
What’s your best childhood memory?
What’s your favorite holiday?
If you could eat only 3 foods for the rest of your life, what would they be?
If you could be a cartoon character for a week, who would you be?

Interesting and funny questions

Is cereal soup? Why or why not?
What is the sexiest and least sexy name?
What secret conspiracy would you like to start?
What’s invisible but you wish people could see?
What’s the weirdest smell you have ever smelled?
Is a hotdog a sandwich? Why or why not?
What’s the best Wi-Fi name you’ve seen?
What’s the most ridiculous fact you know?
What is something that everyone looks stupid doing?
What is the funniest joke you know by heart?

In 40 years, what will people be nostalgic for?
What are the unwritten rules of where you work?
How do you feel about putting pineapple on pizza?
What part of a kid’s movie completely scarred you?
What kind of secret society would you like to start?
If animals could talk, which would be the rudest?
Toilet paper, over or under?
What’s the best type of cheese?
Where is the strangest place you’ve urinated or defecated?
What’s the best inside joke you’ve been a part of?

In one sentence, how would you sum up the internet?
How many chickens would it take to kill an elephant?
What is the most embarrassing thing you have ever worn?
What’s the most imaginative insult you can come up with?
Which body part do you wish you could detach and why?
What used to be considered trashy but now is very classy?
What’s the weirdest thing a guest has done at your house?
What mythical creature would improve the world most if it existed?
What inanimate object do you wish you could eliminate from existence?
What is the weirdest thing you have seen in someone else’s home?

What would be the absolute worst name you could give your child?
What would be the worst thing for the government to make illegal?
What are some of the nicknames you have for customers or coworkers?
If peanut butter wasn’t called peanut butter, what would it be called?
What movie would be greatly improved if it was made into a musical?

Interesting questions to ask a girl

What is something that most people learn only after it’s too late?
If you could change 3 things about your country, what would you change?
What was one of the best days of your life?
If you could trade 1 year of your life for $30,000, how many years would you trade in?
Would you rather have a very long (120 years) comfortable but boring life, or live half as long but have an exciting life packed with adventure?
Who is the most impressive famous person alive today? Why?
What skill or craft would you like to master?
What is something that everyone should everyone be trained to be able to do?
How do you feel about cars becoming fully autonomous and having no steering wheel, breaks, or accelerators?
Besides food/water, medicine, or money what would be the most helpful thing to airdrop to refugees of a war-torn country?

If you didn’t have to worry about money, what would you do all day?
If you could slow down time, what would you do with that power?
Would you rather go to a club, house party, or a small get together of 4 or 5 friends?
What subculture do you wish you knew more about?
What fact amazes you every time you think of it?
What common misconception do you hate to hear repeated as fact?

What is the best way the 1% could spend their money? (Besides just giving it to people.)
What is the best and worst state in the USA? For non-US readers, what is the best and worst province/region/ county in your country?
You have $1,000,000 to make a viral video. What video do you make?
How did you find out that Santa isn’t real?
Why can’t most people keep up with trends in music/fashion/tech as they get older?

Interesting questions to ask a guy

What is the most important object you own?
What simple change could you make in your life that would have the biggest positive impact?
What is something that many people take seriously but shouldn’t?
If you were falsely convicted of a crime, how would you adapt to prison life?
What piece of media (book, movie, TV show, etc.) changed the way you viewed the world? In what way?
When have you been with a person and thought you were equals, but then discovered they were on a whole different level?
What is the most bad-ass quote from a real person you know of?
Which historical figure wins the award for being most hardcore?
What issue do most people think is black and white but you think there is a lot nuance to?
If you have children what career do you hope they peruse and what career would you never want them to get into?

What is your dream job and what makes it so amazing?
What event in your life would make a good movie?
What job would you be absolutely horrible at?
What movie has everyone else seen but you haven’t?
What’s the next big thing?
What commercial convinced you NOT to buy the product they are pushing?
What is the most useless major in college?
What is something most people do easily but you find very difficult?
What job doesn’t exist but should?
What TV news story is getting more attention than it should?
What is the most impressive thing you know how to do?

Interesting questions about beauty

How have standards of beauty changed over the years?
What makes a person beautiful to you?
What is the most beautiful product you own?
Where is the most beautiful place you have been?
Why do humans find things other than humans beautiful? How does it help us?

What is the most beautiful song you have heard?
What features make a natural area beautiful?
What makes a piece of art beautiful to you?
Are there any striking examples of beauty in art?
How does the absence of beauty affect people?
What is the most beautiful thing in your life?
Is beauty only in the eye of the beholder, or can we say some things are universally beautiful?

Interesting and challenging questions

What are some of the biggest challenges you have faced?
Do you enjoy overcoming challenges or do you prefer things to be easy? Why?
What is a challenge you would never want to face?
Do you think living in the present is more or less challenging than living in the past? Why?
What is the most challenging job you can think of?
Do you think that challenges improve a person’s character?

What is the biggest challenge you are facing right now?
What was the most challenging thing about your childhood?
What are some big challenges that people have overcome that you have heard of?
What are the biggest challenges your country is facing right now?
Do you think that the challenges you have faced over your life have made you a better or worse person?

Interesting questions about diet and food

What is the craziest diet you’ve heard of?
What diets have you tried?
Is dieting healthy or unhealthy?
What diets are popular now?
Is dieting an effective way to lose weight and keep it off?

Why do you think there are so many diet trends?
Do you know anyone who has lost a lot of weight on a diet?
Should businesses be allowed to make losing weight mandatory for employees who are costing the business money in missed days due to weight-related health issues?
Will there ever be a miracle weight loss solution?

Interesting questions about family

Who in your family are you most like?
Who is the most generous person in your family?
Do you like going to family gatherings? Why or why not?
How often do you see your parents? How about your extended family?
Have you ever been to any large family reunions? How did it go?

How important are strong family ties to you? Are strong family ties more or less important that close friendships?
How have family roles changed from the past?
Who is the most interesting person in your extended family?
How has your family shaped your personality and who you turned out to be?
What is the best and worst thing about your family or extended family?

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