Interesting Questions to have deep conversations

1. What shows are you into?

Probably at least one or two shows they mention will be shows that you’ve seen and can talk about, and even if not, then you can get them to explain what the shows are about and what they like about them.

2. What do you hope never changes?

A very open-ended question that can lead to a lot of different types of answers, some more interesting than others. It all depends on what direction they want to take it.

3. What’s your dream car?

Another question for getting them to talk about what they love and who knows, it may be a car you’ve also had your eye on, and you can get into a conversation about cars.

4. What job would you be terrible at?

Flipping the common question of their dream job, this question will help you find out what they think they are not good at or at least what they dislike.

5. What movie title best describes your life?

This one can be a lot of fun, especially if you are both into movies. But if you are at a loss, there is always IMDB. Lots of funny answers to be had here.

6. What age do you want to live to?

It can get a bit morbid, but it doesn’t have to. Plus, it helps you to see how they view old age and their place in the world.

7. What takes up too much of your time?

This will tell you a little bit about what they don’t like to do, and probably a bit about what they would rather be doing.

8. What do you wish you knew more about?

We all wish we knew more. The subject might depend on the person. But we all have gaps in our knowledge we’d like to fill.

9. What’s the best way to start the day?

This will definitely tell you a lot about their routines, or at least the routines they wish they had.

10. What mystery do you wish you knew the answer to?

Will it be a personal mystery? A famous mystery? An unsolved case? Only one way to find out.

11. How different was your life one year ago?

With this question, you can find out a little about their past, a little about their present, and probably what they think about how their life is going.

12. What’s the best single day on the calendar?

It could be a holiday, it could be an anniversary, it could be their birthday. Whatever it is, I’m sure there is a reason why they like it and are probably pretty pumped to tell you about it.

13. What are some things you’ve had to unlearn?

This is a great way to learn about what misinformation or mistaken beliefs they’ve had to overcome.

14. What’s your favorite genre of book or movie?

A classic conversation starter, but sometimes those are the best. This is sure to get them talking about a subject they love, and you might even find you have some interests in common.

15. What TV or YouTube channel doesn’t exist but really should?

There are channels of just puppies, fireplaces, and squishing things with hydraulic presses. What other niche channels haven’t made their way into the world?

16. Where is the most interesting place you’ve been to?

Another question that is sure to bring out some interesting travel stories. You might even get a tip for somewhere to go on your next trip.

17. What fad or trend do you hope comes back?

There are no shortages of fads and trends, now it’s time to find out which old trend or fad they remember fondly.

18. What city would you most like to live in?

And if they say they don’t like living in cities, you can ask what kind of countryside or town they would like to live in.

19. What’s worth spending more on to get the best?

Whether it’s food, clothing, or something else entirely, this question will get to the heart of what they value most. Or at least give you an idea of something to upgrade in your life.

20. What are you most likely to become famous for?

Very few people become famous, but everyone has the potential to be. And it doesn’t necessarily have to be something positive. Lots of people are famous because they screwed something up.

21. What fictional place would you most like to go to?

Books, movies, video games, nothing is off-limits. The fictional world is their oyster.

22. Where is the most relaxing place you’ve ever been to?

Time to do a little digging for great vacation spots! And make sure you ask a lot of details because I’m sure they will have a lot to talk about.

23. Who has impressed you most with what they’ve accomplished?

We all have people we look up to, finding out whom they look up to will let you know what they consider to be important work, and it makes for an excellent conversation starter.

24. What job do you think you’d be really good at?

There is so much wasted talent in the world from people doing jobs they aren’t well suited to. Now you can find out what they think they are best at.

25. Where would you spend all your time if you could?

It might be a favorite vacation spot, a favorite bar, or even a movie theater. This question will tell you a lot about what they enjoy and where they like to spend their time.

26. What would be the most amazing adventure to go on?

Everyone’s idea of adventure is different. Some people learn to the more extreme, some to the more mundane. But, however, the person you are trying to get to know leans, you’ll soon find out.

27. What’s the best way a person can spend their time?

This simple question can tell you a lot about their world view. The person might say something like helping the poor, or they might say it’s improving one’s self, or it might just be having fun. Whatever their answer, it will help you to get to know who they really are.

28. What one thing do you really want but can’t afford yet?

Everyone has a list of things they would love to have but are a little out of reach. Always makes for an interesting conversation starter because they already have an interest in whatever it is.

29. What game or movie universe would you most like to live in?

This one is a good jumping-off point into what types of media they enjoy. And make sure to ask them a lot of questions about why they chose that specific universe. Maybe spin it around and talk about the worst universe to live in.

30. What is the most impressive thing you know how to do?

We’ve all got skills of some sort or another. It doesn’t have to be something jaw-dropping, just something interesting.

31. What was the best book or series that you’ve ever read or watched?

Great for getting tips for a new book or series to check out but also a good conversation starter.

32. What question would you most like to know the answer to?

Something big, something small, something personal, or something universal. So many questions. Whatever they choose, it will definitely tell you a little more about them and hopefully spark a good conversation.

33. What are you interested in that most people haven’t heard of?

Another one to get some tips for the good stuff to check out, and you’ll get to learn something new about them.

34. What could you give a 40-minute presentation on with absolutely no preparation?

Whatever the topic is, they are probably an expert in it. And if they are an expert in a topic, well, that’s a great thing to know if you are trying to learn more about them.

35. What amazing thing did you do that no one was around to see?

This one can be a bit of a mixed bag. Sometimes they can’t think of anything, but sometimes it’s something truly amazing.

36. What hobby would you get into if time and money weren’t an issue?

Find out what hobbies they are interested in, and then you can transition into what hobbies they have now.

37. If you didn’t have to sleep, what would you do with the extra time?

This is an interesting question because even though it seems simple enough, it gets to the heart of what they truly would like to be doing with their time if given a chance.

38. What is something you think everyone should do at least once in their lives?

It definitely can be more than one thing, they’ll likely have a few. And it can tell you a lot about what experiences in their life they consider to be significant.

39. What’s something you’ve been meaning to try but just haven’t gotten around to it?

We all have that list of things floating around in our heads that we’ve yet to get to. Now you can find out what’s on their list!

40. What is something that a ton of people are obsessed with, but you just don’t get the point of?

When everyone is jumping on the bandwagon, where do they draw the line? What part of pop culture do they choose to opt-out of?

Who is your favorite superhero? I'm sure that much insight could be gained by understanding the distinctions between a Batman lover and a Wonder Woman aficionado. However, I have a confession: I don't have a favorite superhero, because I don't watch superhero movies. To that end, you could, if you wish, modify it to, who is your favorite fictional character Read my piece for Forbes on Crewmates