Deep Conversation Starters - main in postDeep conversation starters are truly powerful.

…Because whether it’s with friends, colleagues, or significant others, it’s easy for chat to grow stale… we all know:

You can end up having the same conversations over and over, rehashing the same opinions over and over, and never really getting much more than skin deep into how you or anyone. Maybe you’re just looking for a topic that leads to how someone else actually feels.

That’s when you really need a few conversation starters designed to start deep conversations… questions to ask to dive into the more personal—and interesting—topics that you’ve struggled to cover recently. By having a few deep questions to ask in your pocket, no conversation has to struggle with the shallow again.

Using the right conversation starters, there’s no need for the repetitive, useless old chit-chat you’ve likely grown used to. Here are 5 quick steps to teach you how to start and have a deep conversation and 72 deep conversation starters to get you on your way.

72 Powerfully Deep Conversation Starters to Ask

To make this resource even better/easier for you to use… I broke down the conversation starters into a few different sections (from the best starters to use early in a conversation, to deeper ones that are better towards the end).

I recommend looking through each section, but if you want to jump to one in particular, you can use the links below:

The 23 Best Deep Conversation Starters

Deep Conversation Starters - 25 Best Deep Conversation Starters

Once you’ve got the conversation basics down, now you can start considering which deep conversation starter works best for you.

To start with, here are the straight-up 23 best deep conversation starters out there.

1. What’s the best and worst thing about getting older?

Aging is one of the most important things we do, and it leads to many different interpretations. Some people are very relaxed about it, others fret about every gray hair, but everyone thinks about it and has something to say.

2. What will you fight for until the day that you die?

This really cuts to the point: what is so important to you, you’ll never give up on it? If you want to get to know someone, this is a great way to find out the deepest things they care about.

3. Would you take a bullet for someone in your life?

By using such dramatic language, you force your conversation partner to put aside casual friends and really think about who is most important to them. Who is worth risking it all for?

4. Other than money, what else have you gained from your current job?

A great question to ask colleagues and acquaintances to find out how they really feel about work, career, and life in general.

5. If you could change 3 things about your country, what would you change?

No place to live is perfect. If the person you’re talking to is paying attention at all, they’ll have some pretty deep thoughts on what their country needs to reach its full potential.

6. If you could live anywhere, where would it be and why?

If your conversation partner weren’t from where they’re from, where would they want to be from? This opens the door for cultural comparisons conversations.

Deep Conversation Starters - If you could live anywhere, where would it be and why?

7. What’s one downside of the modern-day world?

We all know how good things can seem in the modern day. But what is wrong with modern life?

8. What one thing would you change about our society?

Question five often brings up thoughts of government and politics. Here, you’re focusing more on the behavior of the citizens and the general culture.

9. Would you rather be hated or forgotten?

We live in a time full of celebrities and the constant, always present memory of social media. But how important is it to someone to be remembered? Learn how a person perceives themselves with this question.

10. What’s one thing you think society would be better without?

Would the world be better without the internet? Without consumerism? Without free speech? This question can lead to some very deep—and sometimes controversial—conversations.

11. What small change could the world make to become a better place tomorrow?

Almost the opposite of the last question. Here, you make your conversation partner really think about how to make the world better.

Deep Conversation Starters - What small change could the world make to become a better place tomorrow?

12. What goal do you think humanity is not focused enough on achieving?

Everyone has their passions that they feel the world doesn’t pay enough attention to. Find out how they think humanity needs to improve itself in the future.

13. What desperately needs to be modernized?

This open-ended question could be about something physical (infrastructure, say) or something more conceptual (our ability to see everyone the same, no matter superficial differences).

14. Would you rather be the absolute best at something that no one takes seriously or be well above average, but not anywhere near the best at something well respected?

Is it more important to be the best or to be respected? This question allows you to better understand your conversation partner’s ambitions and also what they personally value.

15. Do you believe in Karma? Why?

Karma is a concept deeply believed by some, entertained by others, and derided by still others. Regardless, everyone has an opinion, and that opinion deeply influences how that person acts.

16. Do your choices matter in the grand scheme of things?

It’s easy to brush aside our actions as insignificant on the big stage of existence, but is there something connecting us and our choices or not? Is there something more to life or are we all alone?

Deep Conversation Starters - Do your choices matter in the grand scheme of things?

17. If today were your last day in your country, what would you do?

This question really presses a person to think about what they love most about their country. It also opens up a path to deep and important memories about why those activities are so loved.

18. If you were to give yourself three challenges right now, what would they be?

Everyone has things they want to improve about themselves, but many people don’t want to discuss them. This is a fun way to explore those deep flaws by an indirect route.

19. Who do you aspire to be more like?

Who we admire is crucial to who we become. Whether it’s a parent or a long-dead historical person, the people we admire suggest who we want to be and how we see ourselves.

20. What current thing do you think is most likely to bring about the extinction of the human race?

A morbid question, but one that tells you a lot about how a person views the world. Do they see environmental catastrophe ahead? Do they see a world war? Or do they see the rapture?

21. Is it worse to fail at something or never attempt it in the first place?

How adventurous is the person you’re talking to? Adventure isn’t just about bravery in the face of injury or death, but bravery in the face of failure or looking foolish.

Deep Conversation Starters - Is it worse to fail at something or never attempt it in the first place?

22. What do you think is more important: exploring the world or yourself?

A great question to set up a conversation about two competing worlds: the one all around us and the one within. Which does your conversation partner draw more inspiration from?

23. What risks are worth taking?

This really tells you what is most important in that person’s life.

24 Deep Conversation Starters for Couples

The deep conversation starters above are great for general conversations. However, sometimes you want to tailor your questions to the special person in your life.

Deep conversation starters for couples focus the attention not just on important topics, but on how they affect the two of you as a unit.

Having deep questions to ask your girlfriend keeps your relationship fresh and allow you to discover some of the more important thoughts your partner may not always discuss openly with you. All you have to do is ask.

Here are 24 deep conversation starters for couples:

24. Is competition good for us?

Competition can make people be their best, it can also cause friction. Should couples compete with other couples? Should they compete with each other?

25. How would you hate us to be described?

By asking this question, you find out your partner’s greatest fears about your relationship, and how important the opinions of others are to them.

26. What kind of old person would you like to become?

How long-term is your partner thinking? This question helps you discover whether you’re central to your partner’s lifelong plans. It also allows you to discuss how you see life playing out on a long timeline.

Deep Conversation Starters - What kind of old person would you like to become?

27. Would you rather have an epic, tragic romance or a satisfying, long-term relationship?

Is your partner more interested in living like Romeo and Juliet or the old couple helping each other across the street? Discuss whether romance or partnership is most important.

28. In what way are you your own worst enemy?

A lot of couple’s arguments aren’t about one partner hurting the other, they are about one partner fighting their own demons and projecting outward. This allows you open up that conversation in a thoughtful and non-confrontational way.

29. What makes you feel accomplished?

To keep a relationship healthy, both parties need to feel the relationship helps make them a success. In order to help your partner feel like a success, you need to know what makes them feel accomplished.

30. Would you rather have a very successful partner or be moderately successful yourself?

Any successful romantic partnership needs to have the interests of both people in mind, but are you or your partner willing to take a backseat for the other to be a success?

31. If you could do anything for someone in your life right now, what would it be and who would it be for?

This question allows you to discuss not only who your partner thinks needs help, but what the problems are and how much they are willing to do for them.

Deep Conversation Starters - If you could do anything for someone in your life right now, what would it be and who would it be for?

32. Do you live more in the moment, or planning for the future?

There are different schools of thought about the best way to think about the time you have. Do you plan for the future or make every moment count? Where do you and your partner fall on this debate?

33. Would you rather be famous when you are alive and forgotten when you die or unknown when you are alive but famous after you die?

Though this is about fame, it also has a lot to do with the question above. It’s really asking: do you live for the moment or the future?

34. Would you rather be alone for the rest of your life or always be surrounded by annoying people?

Everyone has different social needs. This question gives extreme options so you can consider just how important social contact is to your partner.

35. What are you most afraid of losing?

Is your partner materialistic? Or will they think of the people in their life or a personal quality? This deep conversation starter opens up a conversation about what’s most important in life.

36. If you could eliminate one thing from your life today, what would it be?

Find out what your partner feels they should be living without. The same long conversation discussion points from the question above (materialism, people, personal qualities) apply.

Deep Conversation Starters - If you could eliminate one thing from your life today, what would it be?

37. If you could change anything about the way you were raised, what would it be?

If you are thinking about kids long-term, this is an important deep conversation starter to use. You also get some major parenting policy discussed.

38. What was the most important life lesson you learned as a child?

Here, you are looking to discover what wisdom your partner learned either from family or life experience. It’s sure to be something that helped shape who they are now.

39. What do you value most in a friendship?

A romantic relationship isn’t just about romance; it’s also about a deep friendship. To find out more about that side of your relationship, use this deep conversation starter.

40. Would you rather be 100% confident in who you are, or be 100% confident that you’re with the right person?

Any successful relationship requires not just two people who want to be together, but two people interested in making themselves and each other better people.

41. What are your biggest goals in life?

Just like in question 25, making your partner feel like they are accomplishing what they care about is a key to keeping a relationship strong.

Deep Conversation Starters - What are your biggest goals in life?

42. What do you think before getting into a relationship?

Is your partner afraid of starting relationships or excited? You can unlock some important motivations and insecurities your partner feels by asking this question.

43. When do you think it is okay to tell a lie?

Relationships thrive on truthfulness, but they also require a little strategic lying (or at least half-truthing). Where is that line? And how forthcoming is your partner about those sorts of situations?

44. Do you think there’s actually a difference between loving and being in love for someone? If so, what?

How does your partner actually feel about you? You can use this question to launch into a conversation about where you are in your own relationship.

45. Has there been something that’s happened that has forever changed how you think?

You may think you know the major events of your partner’s life, but do you know how they have changed them? This question gives you the chance to see how life changes the person you are with.

46. What’s one thing you feel our relationship is lacking?

It can feel safe to pretend problems aren’t there, but this deep conversation starter lets you find out what makes your partner dissatisfied with your relationship.

Deep Conversation Starters - What's one thing you feel our relationship is lacking?

47. Do you have goals for us?

This gets you to a direct answer of what your partner needs to happen to xyou to make the relationship seem strong and successful.

25 Deep, But Funny Conversation Starters

Some of the above deep conversation starters can feel a little heavy. Maybe you’re just looking for a topic that leads to a good, interesting chat instead of the everyday banter.

In that case, you’re looking for funny conversation starters, questions that can lead to deeper discussions that are still fun and amusing.

Here are 25 deep, but funny conversation starters:

48. If you could live in a virtual reality world, of your own creation, would you?

This question allows you to have an amusing conversation about the world you would build for yourself in virtual reality.

49. Would you rather lose all of your old memories, or never be able to make new ones?

Memories are part of what make us who we are. But are we who we used to be or who we will become?

50. Would you rather travel to the future or the past?

This question is a fun way to explore whether they think the best is behind us or yet to come.

51. Real talk, do aliens exist?

One of the classic conversation starters. Try springing this question suddenly to get a genuine quick response, you can delve more deeply into.

Deep Conversation Starters - Real talk, do aliens exist?

52. If you could write one new law that everyone had to obey, what law would you create?

Everyone has to wear shoes on their hands or everyone has to donate extra food to charity? Silly or serious, this question allows you to have a little fun fixing the world.

53. If you won the lottery, would you still work?

Is work about the money, or is there more to it? This question lets people discuss not just the purpose of work in their life, but also what they would do if money wasn’t part of the equation.

54. What do you look forward to the most when you think about getting old?

A little lighter discussion of aging than you usually come across. Here, you’re not thinking about the negatives of getting old, but all the things that get better with age.

55. If all of life’s constraints were eliminated, what would you want to do every day?

This is a fun way to get at what people really wish they could do with their lives.

56. Would you rather travel to another planet or the bottom of the ocean?

How curious is your conversation partner? And what kind of alien world would they rather explore?

Deep Conversation Starters - Would you rather see travel to another planet or the bottom of the ocean?

57. Would you rather give or get bad advice?

An interesting way to get at questions about selfishness and selflessness. It also leaves the conversation open for some very amusing bad advice stories.

58. If you could replace war with something to settle countries’ differences, what would it be?

War can be a very heavy topic, but finding a better solution can be fun. Should we solve our national problems with thumb wars or rock-paper-scissors?

59. Would you rather be always hungry or always thirsty?

A silly way to tease out some interesting answers. Make sure to pursue why the person chooses one or the other to get to the deeper stories.

60. Would you take your boss’s job if it was offered to you?

How ambitious is your conversation partner? By focusing it on the boss, you can tease out some good personal stories and also some personal feelings about the boss.

61. If you were given $5,000 to give the most amount of happiness to the most amount of people, what would you do?

A chance to let your conversation partner be a little creative and also show their charitable side. This question is very open and can lead to some very deep and novel responses.

Deep Conversation Starters - If you were given $5,000 to give the most amount of happiness to the most amount of people, what would you do?

62. What advice would you give the ‘5-year-old you’?

A chance to discuss mistakes made in life. By making this about a 5-year-old, it limits some of the heavier topics and lets the conversation get a little silly and philosophical at the same time.

63. If you could ‘dare yourself’ what would it be?

It’s fun to dare other people to see the crazy things they’re willing to do, but what about daring yourself? Find out what activities they wish they would do and why they don’t do them anyway.

64. Would you rather be twice as smart or twice as happy?

Here, you can find out what someone thinks makes life more enjoyable. It also gives the chance for people to debate just how smart they think they are now.

65. You have a 10-minute speech to give at a high school, what is it about?

Whether high school was the glory days, the horror days, or the days you’re still living through, it’s a period in your life that leaves an impression.

66. What one invention would you un-invent if you could?

The iPhone or the electric toothbrush? Which did the most damage to humanity? The choices and the reasons to this one can be pretty amusing.

Deep Conversation Starters - What one invention would you un-invent if you could?

67. What’s the most stress relieving thing you can get/do for less than $20?

Be prepared for potentially raunchy and inappropriate answers if you ask this to the right people. You may also discover some interesting, and cheap, things to do along the way.

68. What’s the best conspiracy theory you can make up on the spot?

This one works best with a group, since conspiracy theories are great to build off one another. Once the ball is rolling, you can really end up in some pretty bizarre and hysterical places.

69. Would you rather take a vow of celibacy or take a vow of silence?

Talk about a tough choice. This makes people prioritize their lives and their needs in an amusing way.

70. Would you rather be happy and content, but not achieve much or never be satisfied but achieve a lot?

One last final version of this question. Here, happiness and satisfaction are directly thrown into the conversation to get to the real truth about just how ambitious your conversation partner is.

71. Would you rather ask for help or figure it out yourself?

A great question that reveals how independent someone is. This is a great question for colleagues to help gauge whether they would work better in teams or alone.

72. Would you rather know everything or be amazing at any activity you tried?

The last of our deep conversation questions, but one of the best. An age-old question about whether it would be a blessing or curse to know everything.

Deep Conversation Starters - Would you rather know everything or be amazing at any activity you tried?

How to Start and Have a Deep Conversation

1. Think about who you are talking to

When you think about how to start a conversation, and particularly how to start a deep conversation, the first thing to consider is your conversation partner’s relationship to you.

If they are your romantic partner, you may feel any topic is open, but a colleague or acquaintance may require some limitations and a more careful discussion, one aimed at less intimacy and more superficiality.

Also, don’t forget to focus your talk not just on what makes you curious, but what interests the other person as well.

2. Choose the right place to have a serious and long talk

Some venues lend themselves to intimate conversation: cafes, museums, the right bar. Other places do not, like rock concerts or a boardroom right before a meeting. If you want your conversation to be successful, pick a place where the setting encourages a good chat.

3. Choose the right deep conversation starter

Once you’ve settled points one and two, choose the deep conversation starter that best suits the other person, their relationship to you, and the setting you’re in.

4. Share your own opinions, but focus on asking more questions

In the course of conversation, you will be called upon to answer your own questions and share your opinions as the conversation gets going. Be sure to be forthcoming, but try to keep the conversation focused on the other person.

To push forward from topic to topic and to dig deeper, ask questions instead of offering up big statements.

5. Have fun and don’t get heated

Deep Conversation Starters - Think about who you're talking to

When you start a deep conversation, there’s always the potential for opinions to get controversial. Keep in mind that these opinions are probably deeply held. You don’t have to agree with them, but try to avoid becoming offended or offensive.

The best way to avoid offense is to keep things light. Allowing humor into your conversation will keep things playful and keep your conversation partner from getting worked up.

Looking for More Deep Conversation Starters?

By now, you should have some great ideas for questions that you can ask to start a deep conversation… but if you want more, we’ve got you covered:

  1. These Deep Conversation Topics will give you some great inspiration for deep topics to talk about.
  2. Want to things to the next level with a beautiful woman? Try these Deep Questions to Ask a Girl.
  3. Ponder the same questions that ancient philosophers like Plato and Aristotle did with these Philosophical Questions. They’re interesting to think about and usually spark a great, deep conversation when asked.

In Conclusion

Conversation is one of the most important ways we interact.

By taking your conversation starters game to the next level and finding the right questions to ask, you not only learn more (and more interesting) things about the people you talk to, you show that you too are a deep-thinking, interesting, and amusing person who isn’t satisfied by everyday chit-chat.

Whether you are looking to break away from stale conversation with friends or a romantic partner or find a creative way to learn more about colleagues, finding the right deep questions to ask will provide you all you need to have some great conversations.