20 questions to ask someone if you want to start a deep conversation

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When you were a kid, I bet you played 20 Questions on long car rides or at school with your teachers and friends. 

But those 20 questions were just shallow yes/no questions designed to guess the answer to a riddle, and they certainly didn’t teach you much about life.

If you want to get into truly thoughtful and profound conversations that help you make connections and learn more about others, the world, and yourself, you need to go deeper.

So rather than playing a children’s game, here are 20 questions to ask someone if you want to start a deep conversation.

1) Do you think people are inherently good or bad?

We’re starting with a heavy one right out of the gate!

Philosophers have been hitting this ball back and forth since there was philosophy, and moms have been doing it even longer.

You’ve got Plato, Mencius, Rousseau, and more in the good camp against Xunzi, Kant, Hobbes, and their supporters in the evil camp. 

But ask someone to really think about this one, and you may find a whole new perspective on human nature.

2) What’s the hardest thing you’ve ever had to do?

When you’re working through your own struggles, and especially when you’re stuck, one of the best things to do is look for inspiration from others.

Your conversation partner doesn’t have to know the details of your issue, nor even have gone through the same thing.

But this question can not only reveal a ton about the other person’s character but also give you ideas for dealing with the problems that you’d never even considered before. 

3) What can’t you live without?

This question seems pretty shallow on the surface.

But like a murky lake, one more step might land you deep underwater.

Answers can even start out superficially, like food or music, but once the conversation has started, you can guide things deeper.

That might help you really get to the core of the other person to see what they value above all else.

4) What will the world be like in 50 years?

This is a question that can send your conversation off on a limitless number of paths.

Most people will probably start thinking about the rapid pace of technological change we’re experiencing now and try to predict where it will go in the future.

But what about entertainment, social change, health, and even love?

We’re some of the first generations to fathom just how different the world could be in just half a lifetime, so why not delve deeper into this fascinating topic?

5) What has formed you to be the person you are?

This question is intensely personal, and you might have to choose carefully who you ask it to.

It can provoke some very profound reflection on the part of your partner and even stir up some difficult memories. 

But don’t let that scare you – let it inspire you to form a deeper connection with that person by sharing these intimate remembrances.

6) What you’re earliest childhood memory?

Since we’re delving into the past, here’s another great question to ask someone if you want to start a deep conversation.

Most people can’t remember much between the ages of two to six due to a phenomenon called childhood amnesia.

So anything that does come through is likely a very profound and identity-influencing memory that has stuck with that person for such a long time.

Just be warned that this question could be triggering for some people, so ask it with sensitivity.

7) What’s the first thing you ever bought with your own money?

This is another great memory question.

It helps people sail back in time to one of their first hedonistic experiences and may give real clues into the nature of what they truly want.

8) What happens to us after we die?

We’re not shying away from the big ones here!

While many people will simply refer to what their faith teaches, it’s unlikely they’ve thought too much about the details.

Will we eat? Will we have to sleep? Will we have bodies?

Keep forging ahead down this path for some extremely engaging conversation.

9) What is love?

Sorry for making you think about the 1993 dance hit from Euro-pop artist Haddaway.

This can actually be a serious question, especially if you add the words “really” or “to you” at the end.

You might find out that love means a great many things to many different people.

And if you ask your partner or a potential one, you’ll probably learn a whole lot about their love style and whether or not you’re compatible.

10) What’s the best thing that could happen for you right now?

This question is intense but also intensely positive.

It taps into the other person’s hopes and dreams and may even help them talk about their needs and struggles with a sense of optimism instead of dismay.

11) If you could go anywhere in the world right now, where would it be?

Since most of us can’t, this question is more a way to get people to talk about their dreams than anything else.

But the experiences people long for tell us a lot about what they truly want and also what might be missing in their lives.

12) Do you believe in extra-terrestrial life?

This is one of the most interesting questions out there for two reasons.

It lets you know a lot about the person you’re dealing with (practical, a dreamer, even an abductee?).

But it can also get deeper into the mysteries of life, like why we’re here and where we came from.

What’s deeper than that?

13) What makes you you?

Well, maybe this one.

Who are you, really?

Biologists tell us that half the cells in our bodies don’t share our DNA.

And what about the nature of consciousness?

I honestly can’t think of a deeper topic to get into, and it honestly scares me more than a little!

14) “Where does love go when it goes?”

I’m pretty sure I stole this one from author Tom Robbins who has some pretty interesting answers of his own.

Sometimes love can seem like something tangible that you can reach out and grab.

So where does it disappear to?

This question sounds silly but trust me – it will help bring you into a deeper discussion of what love really is.

15) What do you want people to remember about you once you’re gone?

Legacy is what this question is all about.

So many of us don’t think much about it when we’re young, but as the clock starts ticking…

People’s responses might start with achievements, but with some light digging, you can get a whole bunch deeper into what truly makes this person tick. 

16) What are you most afraid of?

A lot of people talk about their legacy and being remembered when you ask this question.

Others might reveal phobias or real, practical fears.

A little probing might just find the deep, dark, scary things which motivate that person more than anything else!

17) What do you need forgiveness for?

As an alternative to the more common, “What’s the worst thing you’ve ever done?” I think this question is even more revealing.

So many people hold onto things that weigh them down, and opening up with a question like this might be a way to really help someone unburden themselves.

18) If you could bring someone back from the dead, who would it be?

The depth of the conversation you start here might depend on the other person’s experiences with loss. 

Younger people might choose historical figures like Albert Einstein or Cleopatra.

But older people and those who’ve encountered loss will talk about people they knew and loved.

This question can begin a deep conversation about love and loss, even though it might be a painful one.

19) If you could do anything over again, what would it be?

Like the previous question, people with more life experience will give you deeper answers.

Still, they might be a lot more surprising than you’d think.

Some people would talk about huge mistakes or their biggest regret, but others might look at this as the opportunity to re-live and re-experience something wonderful.

20) Would you like to go to space?

This question is deep without being too heavy emotionally.

Earth is pretty good for us humans, so it would be interesting to hear perspectives on why heading into the deep, dark unknown could be enticing.

Deep conversation starters

These 20 questions are just examples of ways to get past small talk and get things to a deeper level.

But don’t forget that timing, tone, body language, and choosing the right partner are just as important for deep, meaningful conversations.

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