Conversation Starters: 100 Fun Questions to Get to Know Someone

The best conversations start with the right questions/conversation starters!

Let’s be real – small talk is the worst. You know the drill: “How was your day?” “Good. Yours?” And just like that, the conversation dies.

But what if you had a way to spark deeper, more meaningful (and sometimes hilarious) discussions that actually make you feel connected?

That’s where these conversation starters can help! Whether you’re getting to know someone new, deepening a relationship, or just looking to liven up a dinner party, these questions are guaranteed to turn any chat into an unforgettable one.

Some are fun, some are deep, and some might just surprise you. Ready? Let’s dive in.

100 Conversation Starters/ Questions to Get to Know Someone

If you became Earth’s official tour guide to aliens, where would you take them?

If you could turn any activity into an Olympic sport, what would you have a good chance of winning a medal for?

What would you be happy doing each day if you didn’t have any worries about now or the future?

What song best defines your life?

Have you ever had to break up with a friend? What was the reason?

What’s the most spontaneous thing you’ve ever done?

If you could invent a new holiday, what would it be?

Will people still get married in the future, or will relationships evolve into something completely different?

Do you think it’s ever possible to be an overnight success?

Do you think we’ll discover intelligent alien life in our lifetime? If so, what should our first message be?

If you could erase one thing from your brain/memory, what would you choose and why?

If you could explore the deepest oceans, get on a rocket to space, or visit 60 countries, which one you choose & why?

What is one phrase you wish you could ban from everyone’s vocabulary?

Fast forward 20 years… what does life look like now?

What’s a valuable life lesson you’ve learned so far?

What would be the title of your autobiography?

If you could go back and relive your high school years knowing what you do now, what would you do differently and why?

What’s the most thought-provoking documentary or TED Talk you’ve watched?

As a child, what rules were made to be broken?

Where in your life are you living in a bubble?

If you could bring back one extinct species, which one would it be and why?

What do you have absolute faith in?

How do you imagine you’ll spend your retirement?

Do you think some people are born evil, or does it depend on their environment?

Describe a life lesson that took you more than once to learn.

Your diary is clear and you have a day just for you. What do you do?

What’s the most profound experience you’ve had in nature?

You’ve won 1 million dollars in the lottery. What is the first thing you do?

If you could be a fly on the wall for any conversation in history, which one would it be?

What’s the last thing you changed your mind about and why?

What controversial opinions do you enjoy sharing with others?

Humanity 2.0 starts on Mars. How do you decide who joins?

If you could pick a new first name, what would it be?

What do you value most in a friendship?

What historical event do you wish you’d experienced first hand?

Do you believe in love at first swipe?

What’s one thing that always makes you laugh, no matter how often you’ve seen or heard it?

If you could shape-shift into any animal but had to stay in that form for a year, which animal would you choose?

What’s a deal breaker for you in a relationship?

What would your dream treehouse look like?

Do you believe retirement should be about relaxation, or do you think retirees should stay productive?

How do you think technology will change the way people experience retirement in the future?

What do you think about advances in AI? Does any of it concern you?

Which teacher had the biggest impact on you and why?

You meet a time traveler from 200 years in the future. What questions do you ask?

What’s your favorite “bad” movie?

What act of self care should become a non negotiable in your life?

For 24 hours, time stands still for everyone except you. What do you do?

What’s the most interesting fact you know?

If you were a meme, which one would you be?

What’s the weirdest food combination you’ve ever tried that was surprisingly delicious?

What lie did your parents tell you because they thought it was in your best interest?

Would you rather fight one horse-sized duck or 100 duck-sized horses?

How are you creating a life well lived?

What’s the best advice you received from your mother?

What do you think is the funniest movie ever?

What is the most unbelievable fact you know?

Have you ever lied on your resume to get a job?

If you had the power to solve one global issue, which would you choose?

If money was no object, what would you buy?

Have you ever been mistaken for someone else? What happened?

What’s your biggest fear about retirement, and how do you plan to overcome it?

What’s the most embarrassing thing you’ve ever Googled?

Who is your celebrity crush?

Do you think children today are growing up too fast?

What values do you think will be most important for children to learn in the future?

What do you think Deja-vu is all about?

If you were a ghost, where would you haunt and why?

What would your 10 year old self think of your present self?

Who and what should you never be trapped with inside an elevator?

What is the most unusual item in your house?

What’s your favorite thing about yourself?

What is the most precious thing that you’ve lost or broken?

What is the easiest way to break your trust?

What’s the funniest Wi-Fi name you’ve seen?

If you could start a charity, what would it be for?

Do you ever experience repeat dreams about a past life?

What’s a quote or saying that you live by?

Of anyone in the world, who do you want to trade lives with?

What’s the longest you’ve ever gone without taking a shower?

Do you find yourself judging others? If so, in what way?

What do you think happens after death?

What superpowers are more inconvenient than they are useful?

What beliefs would you want to pass on to your children or grandchildren?

What would you like to do, learn, and explore if you could make time stand still for 6 months?

What has been the best phase in your life up until now?

What’s one thing you only do when you’re alone?

What subjects do you think children should be learning in school that they aren’t being taught now?

What’s the craziest conspiracy theory you’ve ever heard?

If you could learn the truth about one unsolved mystery, which one would you choose and why?

If you could live anywhere in the world for a year, where would you choose and why?

What is something you despise that everyone else seems to love?

Do you think children in the future will have more or less creativity because of AI?

What have you learned about love?

What’s the best vacation you’ve ever been on?

What’s the most bizarre dream you’ve ever had?

Do you think personal privacy will still exist in 50 years, or will it be a thing of the past?

What’s the biggest challenge children of the future will face?

If you were to start your own business, what kind of business would it be?

Have you ever experienced something supernatural?

Want Even More? Let’s Keep the Conversation Starters Going!

If you love these conversation starter questions, imagine having 300 more at your fingertips – perfect for date nights, road trips, game nights, or even journaling!

That’s exactly why I created the 300 Conversation Starters Printable Bundle – so you’ll never run out of things to talk about.

🎉 BONUS: You’ll also get 100 Would You Rather questions to add even more fun to your conversations!

👉 Grab your conversation starters here and start sparking amazing conversations today!
Click here to get yours now!

Because the best moments in life? They start with a simple question. 

If you liked these conversation starters, you might also like these other conversation starters too: 

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Check them out for more awesome conversation games!

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