Deep conversation starters are essential for when you want longer conversations, and this list has plenty of them for you!

I have written and published countless articles on the best conversation topics so you too, can be an expert conversationalist. I've had my work featured on, iHeart Media, Elite Daily, and many more!

I know the right questions to ask as excellent conversation starters for any situation. So, let's get into the perfect deep questions to ask to start having those deep conversations.

Let's go!


70 Best Deep Conversation Starters

1. What will you fight for until the day you die?

Why It's Great: This really cuts to the point: what is so important to you that you'll never give up on it? Some of the many reasons to fight may be for love, family, power, freedom, sacrifice, or pride. Other situations can lead to conflict between individuals, such as oppression, race, and cultural differences.

Who To Ask It To: If you want to get to know someone, this is a great way to find out the deepest things they care about. This will turn casual friends into lifelong ones by building a solid connection.

Who NOT To Ask It To: This can be a sensitive topic for those who have literally fought for someone until their death. For instance, a person who has lost their loved one recently.

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

Why It's Great: People may come to realize that earning a living involves more than just financial gain by asking this question. Another reason can be that job satisfaction is more essential than your income.

Who To Ask It To: This is a great one to ask colleagues and acquaintances to find out how they really feel about work and life in general. Money isn't always what makes a job worthwhile, after all. This could start a good conversation about work experiences.

Who NOT To Ask It To: Jobless people, definitely. It can be really rude of you to ask them this question knowing that they're unemployed or barely able to support themselves.

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

Why It's Great: Everyone has an ideal location where they'd rather live. Whether it's somewhere with a warm, sunny climate or somewhere with snow falling on the windows every morning, personal questions like this can say something about a person. This subject also opens the door to talk about various places' cultural differences.

Who To Ask It To: This is a common conversation between married couples but it can be used in plenty of situations. Couples often have differences in where they'd like to live, and this could help settle that.

Who NOT To Ask It To: There are underprivileged people who can barely afford housing for themselves and their families. Be cautious about who you ask and find the appropriate timing on this one.

4. Would you rather be hated or forgotten?

Why It's Great: We live in a time full of celebrities and the constant, ever-present social media. Imagine going through some of the experiences they have and having actual anti-fans. How important is it for someone to be remembered and immortalized? This can be used as a fun conversation starter, and would-you-rather questions surely don’t disappoint!

Who To Ask It To: You can ask this to someone you have a considerable connection with or anyone who takes the question at face value.

Who NOT To Ask It To: It wouldn’t be appropriate to ask this question to someone who’s had a terrible or traumatizing past experience with others and their opinions.

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

Why It's Great: This discussion can lead to some very deep and sometimes controversial exchanges. Would the world be better without the Internet? Without consumerism? Without free speech?

But what's a better way to build a deep connection with someone than getting engrossed in meaningful conversations together?

Who To Ask It To: Why don’t you use this during small talk with students? Young minds have much more varied opinions than adult ones do, so it'll lead to some very interesting answers.

Who NOT To Ask It To: Actually, you can ask this to anyone. Everyone’s living on the same earth, aren’t we all?

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

Why It's Great: This really presses someone 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. When you're trying to build a stronger connection with someone, learning what they appreciate is important. Indeed, this is an intriguing subject. One can make thousands of realizations on the value of their own ethnicity with this.

Who To Ask It To: You can ask anyone, but someone who travels a lot is probably the best person to ask this. They'd know a lot about spending your last day someplace before moving to the next.

Who NOT To Ask It To: Those who could care less about their country aren't worth asking. Spare yourself the time and only ask those whom you want to personally know more about!

7. Do you believe in Karma? Why?

Why It's Great: Asking deep personal questions like this really makes the person you're asking think. Karma is an interesting topic, too, because while we're aware it may exist, some of us don't choose to be affected by it.

Who To Ask It To: If you’re on a date night, be blunt and ask your girl this exciting question. Make sure to follow up with what karma she thinks you have, too.

Who NOT To Ask It To: There are some people whose cultures and beliefs don't involve believing in Karma. Naturally, you'll want to avoid being rude by asking this.

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

Why It's Great: This is great to ask guys, especially because guys love challenges. They want to know how to be a better man, but many don't know where to start. So being asked this can either give a guy some ideas or have them share their own.

Who To Ask It To: Naturally, you can ask this of any guy, but you can really ask anyone. Here's an idea: ask this question to your colleague or your boss during lunch. Getting their perspectives can really teach you more about them.

Who NOT To Ask It To: Be careful about asking friends who are facing these sorts of challenges right now. It could trigger their stress.

9. Who do you aspire to be more like?

Why It's Great: You can learn a lot about someone by asking this, and not just directly. Whether it's a parent or someone inspirational that always has the right words to say, the people we admire suggest who we want to be. So, you'll be able to learn their answer and learn about who they want to become in the future.

Who To Ask It To: This is a good conversation starter when talking to someone whom you already look up to. You can take advantage of their answer and use it to improve yourself as well.

Who NOT To Ask It To: There's no wrong person to ask. Don't we all aspire to become more like someone or better than what we currently are?

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

Why It's Great: This way, you can phrase asking whether they're an extrovert or introvert in a much less ordinary way.

Who To Ask It To: You can ask anyone, but it's better to ask adults rather than teens or younger. The latter is still in the formative stage, where they're deciding what to choose.

Who NOT To Ask It To: Asking a deep question like this to strangers you’ve just met, at a networking event, for example, can startle them. Give it some time past the introduction stage.

11. What’s the hardest thing you’ve ever been through?

Why It's Great: You've given them a reason to give a deep thought about their past, and that helps them open up to you. Naturally, you'll also learn how they've overcome it.

Who To Ask It To: Reunite with your high school best friends and open with this question. As they share their answers, you'll also have time to catch up with them and give your own.

Who NOT To Ask It To: The topic of life challenges is a sensitive topic for those dealing with their mental health. Spare them this question until you're sure they can handle it.

12. If you found out you were going to die tomorrow, what would you do today?

Why It's Great: Our mortality is always a deep conversation topic. It has you really thinking about what's most important in life. Are there fun things you've always wished to do? You can follow this up in so many ways.

Who To Ask It To: This one's perfect for asking close friends or even your partner. A solid friendship is built on whether we can choose to spend our last day with someone we love.

Who NOT To Ask It To: It'd be awkward nonsense if you ask your ex this one, wouldn't it? I bet you definitely wouldn't want to hear them say they'd spend it with you.

13. Can a positive outlook make any situation better?

Why It's Great: You'll get a great debate going between the optimists and the pessimists about everyday life and whether a positive outlook has an impact. Everyone has their own opinion, so you'll have a lot of different answers.

Who To Ask It To: This is always a good conversation starter among newly-found friends or partners! Talk it out with wine or over a meal, and you've got a recipe for a fun time!

Who NOT To Ask It To: Pessimists might not be the best people to ask this to, unless you're interested in what they have to say.

14. If you could go back and do one good deed that you had the opportunity to do but didn’t, what would it be and why?

Why It's Great: This is sure to be a deep and interesting conversation. When did they miss out on being the hero? Why did they fail, and how would they change it now? Swapping stories and digging for more details by asking the right questions really helps you have a deeper connection.

Who To Ask It To: You could ask close family members or friends about this - basically, people you know well. They could provide their perspective on why they didn't do it.

Who NOT To Ask It To: Asking someone who has gone through tremendous tragedy, grief, or a highly private and delicate issue would definitely be inappropriate, so avoid asking this.

15. How would the people closest to you describe you?

Why It's Great: It may seem like a personal thing to ask, but it's a great way to get to know someone because it can reveal how they see themselves. Are they honest, responsible, or messy? Are they simply just sharing their opinion about themselves, or do they really believe it's how their friends and family see them? This can spawn plenty of meaningful conversations, so be prepared to spend a while.

Who To Ask It To: The best people to ask this question would be someone whose family and friends you know. That way, you can ask them afterward, and compare their answers.

Who NOT To Ask It To: Some people don't like being asked about their closest friends, so wisely change the subject if you encounter that.

16. What age do you feel on the inside?

Why It's Great: Talking about age and life is something so universal; everyone knows how to answer it, which makes it something anyone can ask. Are they older than their years or still a child at heart? The answer can be profoundly deep and great for talk.

Who To Ask It To: Just about anyone can be asked, but it's ideal to ask someone who is old enough. They can feel younger than they actually are or even older - the answers are all different.

Who NOT To Ask It To: I completely flopped this one when I asked it for the first time. It made the other person think I was calling them old - that's because I asked it while laughing. So, be a little careful when asking this, and make sure to be more welcoming than amused when you ask it.

17. Is there ever a time when giving up makes sense?

Why It's Great: It's important to know whether a person would give up, but also why. Learning about it can really teach you whether your friend has plenty of determination or if they choose to wisely retreat and fight another day.

Who To Ask It To: This can be asked not just as a way to start a conversation, but you can also ask a professional about this for advice. As long as it spawns a deeper conversation, it's fulfilled its purpose.

Who NOT To Ask It To: People who were forced to give up something are not a good choice for this question. This also includes people afraid of failure.

18. How would you describe ‘freedom’ in your own words?

Why It's Great: Being asked to describe something in your own words can really tell you a lot about them. Freedom is difficult to define, and we all have different things to say about what it really means. One guy's idea of freedom could be another guy's idea of being held back or held down. So, you'll have an interesting array of perspectives from this.

Who To Ask It To: Those who are fond of philosophy are the best ones to ask or those with particular personal philosophies.

Who NOT To Ask It To: People who have had issues with freedom in the past aren't the ones to ask. An oppressed group will likely not respond kindly to this.

19. What makes everyone smile?

Why It's Great: With this, you're not just asking what makes them smile specifically - but what creates smiles in everyone. That makes it immensely relatable.

Who To Ask It To: Everyone! We all have differing opinions, but asking them what makes people smile can make them smile, too.

Who NOT To Ask It To: Some people might find it difficult to smile when they are going through hardships or facing personal issues. Look for their expression, and make sure not to ask when they're obviously down.

20. What is the most valuable life lesson you learned from your parents?

Why It's Great: This is a chance to compare the wisdom passed down from the last generation, which could also lead to them talking about their family.

Who To Ask It To: People who often refer to their family, as well as those who have learned many life lessons from them.

Who NOT To Ask It To: For those who don't have a family or otherwise have a bad relationship with them, it's best to avoid this.

21. What would you wish to accomplish in life if you could only accomplish one thing?

Why It's Great: Of all the things someone can talk a lot about, it'd be a dream or goal they have, so this is an automatic hour-long conversation!

Who To Ask It To: Asking this question to someone you trust, such as a friend, mentor, or family member, would be best. They have a unique viewpoint, one which relates to yours.

Who NOT To Ask It To: Someone who has failed to accomplish their goals in some way wouldn't be a good target.

22. What's one thing you would change about yourself?

Why It's Great: We all want to change, but we don't often tell people how. This question brings that topic to the fore.

Who To Ask It To: Anyone! That said, it's best to ask someone you know fairly well, so you can witness the change yourself.

Who NOT To Ask It To: Self-conscious people may not like being told they're someone who needs to change.

23. Do you think there is something special about a person's first love? Why?

Why It's Great: It allows people to express their ideas on love and relationships by talking about their first love. This can bring back fond memories, arouse strong feelings, and shed light on how they view love.

Who To Ask It To: It's great to ask someone who's had a first love, of course. That being said, even those who haven't found love yet can provide surprising viewpoints.

Who NOT To Ask It To: Naturally, someone who's recently had a bad experience with love is out of the question.

24. What are the three things that you cannot live without?

Why It's Great: This question frequently starts interesting conversations, every time I've used it. Plenty of times, I've asked, and made sure that their phone isn't an option - this keeps it interesting 'til the end.

Who To Ask It To: You can close friends, relatives, or other acquaintances who are open to engaging in deeper conversation. Keep their boundaries in mind, though!

Who NOT To Ask It To: This is as inoffensive of a question as possible, so realistically, there's really no one you can't ask.

25. What is the most dangerous/adventurous thing you have ever done?

Why It's Great: Some kinds of risks are worth taking, and talking about them can be a seriously fun conversation. It enables people to connect over similar experiences or relate to each other's exciting stories!

Who To Ask It To: Those with a reputation for being daring or who have shown a desire to partake in adventurous activities can have fascinating tales to tell. Extreme sports enthusiasts, people who have visited extreme areas, or those who have had thrilling encounters may have fascinating tales to tell!

Who NOT To Ask It To: There's no one general person you should avoid asking, but people react to the idea of risks in different ways. It's best not to ask people who find risk-taking too frightening.

26. What totally impresses you?

Why It's Great: This fun question fosters connection and discovery by enticing people to share the things that impress them. Make sure to keep their answer in the back of your mind for later!

Who To Ask It To: Girls are more easily impressed than guys, so it's always a safe bet to ask them If you want to know how to impress a girl, it's important to pay attention to the things she says here - you could end up being the one to impress her instead.

Who NOT To Ask It To: There's no wrong person to ask. Everyone is bound to be impressed by something.

27. What is your number one goal for the next six months?

Why It's Great: A meaningful connection can be made when you start opening up to someone about your goals and dreams, which is what this question does. You're shrinking the size of the field to six months to get a genuine and clear answer.

Who To Ask It To: Asking someone you're in a relationship with is the best one for it. With this, you give them the chance to consider their personal ambitions and their future dreams!

Who NOT To Ask It To: Asking someone who just ended a long-term relationship wouldn't be advisable. The question could unintentionally bring up memories of their previous relationship.

28. What makes you feel proud?

Why It's Great: Is it family? Is it their career? Is it a talent? Regardless, it's sure to be an interesting subject matter to discuss. Watch them beam with pride as they talk about things that give them a strong sense of self-worth.

Who To Ask It To: Ask this to someone who enjoys sharing their favorite memories, be it your relatives or anyone you’re close with! It can inspire them to think back on moments that made them feel proud and happy.

Who NOT To Ask It To: Those with low self-esteem shouldn't be asked this, especially if they're frequently plagued with issues regarding self-worth.

29. When have you worked hard and loved every minute of it?

Why It's Great: Whether this brings to mind a volunteering experience or a great day at work, it's pleasant to watch someone talk about something with pride - whether it be working hard or hardly working.

Who To Ask It To: A go-getter or achiever or someone who has a positive outlook when it comes to working on something.

Who NOT To Ask It To: Someone who you know doesn't like work in any shape or form. Not only will it be a dull conversation, it won't end up being very deep or meaningful.

30. Who or what do you think of when you think of love?

Why It's Great: The question encourages expressing oneself and opens the door to enthusiastic conversations about experiences with love. Love is a universal language anyone can relate to, so this will get you a good conversation.

Who To Ask It To: You can start here and move on to the nature of love and how it relates to your girlfriend’s first answer. It's also a good opportunity to talk about how people show love and how to tell a girl you love her.

Who NOT To Ask It To: Asking someone who may have gone through loss, pain, or heartbreak is best avoided. Love can hurt sometimes, and it harms the healing process to bring it up.

31. Is competition good for us?

Why It's Great: Competition can make people be their best selves, but it can also cause friction. Should couples compete with other couples, or should they compete with each other? What does your partner consider healthy rivalry? These are all important questions to ask.

Who To Ask It To: Your partner, naturally. This is a question that strengthens your bond as a couple. You and your partner can always test each other’s sportsmanship by playing games like truth or dare for couples. Some dare questions are tough, but competitiveness might be all the push you need.

Who NOT To Ask It To: Ironically, it can also be your partner. Competition is a sensitive subject for partners who want their relationship to remain tame, so tread lightly when asking. You'll only know whether it's great to ask based on your own experience.

32. How would you hate us to be described?

Why It's Great: Asking these sorts of questions can spark some interesting debates and discussions. You're not just asking how you would hate to be described, but how you and other people collectively are. That makes it an interesting and unique question.

Who To Ask It To: You can ask your partner or a group of friends you're close with. As long as you can all be described as a group, the question works for it.

Who NOT To Ask It To: However, it would be absurd to ask this to just some random person. Besides being awkward, it would be weird to be described as a collective with someone you barely know.

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

Why It's Great: This discussion allows you to open up that can of worms in a thoughtful and non-confrontational way. You're not just asking them if they're their own worst enemy, but why.

Who To Ask It To: Ideally, you should be asking someone you're close with or your romantic partner. Many couples' arguments aren't about one partner hurting the other; they are about one partner fighting their own demons and projecting outward. Knowing the why can help you form a deeper connection.

Who NOT To Ask It To: Asking someone who is already experiencing self-doubt, self-criticism, or low self-esteem isn't advised. There's just too much potential to give them a negative self-perception.

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

Why It's Great: It gives you the chance to discover whether they prefer to share in the success or support the one achieving it.

Who To Ask It To: Everyone who's either found a partner or wants to find one can work! As long as they envision a life with someone else, they'll have an answer to this.

Who NOT To Ask It To: Asking others who fear comparison or are insecure about their own accomplishments is best avoided. You wouldn't want to provoke self-doubt in them, do you?

35. Do you live in the moment or plan for the future?

Why It's Great: With so many different ways to think about the time you have, we all have our own deeper thoughts towards this subject, making it great to ask anyone whom you're close with.

Who To Ask It To: Anyone! This is a question where it's mostly one or the other, meaning there are not many people who are undecided about it.

Who NOT To Ask It To: People who fear the future in some way may be avoided it, but this is a question that is safe to ask most about.

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

Why It's Great: This is a probing query that may ignite a heated debate and give you insight on what a person hates most. Even information about something someone hates can be interesting to learn.

Who To Ask It To: Someone close to you, ideally. This is a would you rather question that gives extreme options, so it should only be asked of people you know can handle it.

Who NOT To Ask It To: A person who values their privacy or finds comfort in solitude may find this question's choices to be disturbing or unsettling. Everyone has their sensitive spots, so be mindful when asking.

37. What are you most afraid of losing?

Why It's Great: This opens up a discussion about what's most important in life. Is it the possessions we own, or the people we love?

Who To Ask It To: Is the person you're asking materialistic? You can add a challenge to the question and actually make them choose a material object. It keep things interesting.

Who NOT To Ask It To: Someone who has experienced a great deal of loss would naturally not react well to the possibility of losing more, even if it's only implied.

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

Why It's Great: If you are thinking about kids in the long term, this is an important discussion to have. It's a chance to talk about some major parenting policies and expectations.

Who To Ask It To: Deep talk before bedtime is always a good practice with your partner. The key to keeping a strong relationship is making sure you're on the same page regarding crucial decisions.

Who NOT To Ask It To: Unintentionally, this inquiry could cause someone to recall previous traumas or terrible upbringing. Be considerate and think before you spill!

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

Why It's Great: It's an interesting quandary, one that I'm sure people would love to answer.

Who To Ask It To: Someone whom you believe can trust you enough to admit that they would lie. Or someone who isn't bothered about these types of questions.

Who NOT To Ask It To: Someone who values the truth and trusts deeply. The idea of lying may be appalling to them, even if it's only hypothetical.

40. What's one thing you feel our relationship is lacking?

Why It's Great: It can feel safe to pretend problems aren't there, but this deep conversation starter lets you discover what makes your partner dissatisfied with your relationship. It's great to know where there is room for improvement.

Who To Ask It To: Who else but the person you're in a relationship with? A friend can do just as well, but it's most definitely worth discussing with your significant other.

Who NOT To Ask It To: You shouldn’t ask anyone you barely know this question. Only you and someone you're close with would know the shortfalls of each other, anyway.

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

Why It's Great: This is a funny get-to-know-you inquiry about the world you would build for yourself if you could. How creative are your conversational partners, and what sort of world would they create?

Who To Ask It To: You should ask this funny conversation starter to someone who might have an idea for an ideal world.

Who NOT To Ask It To: Some people find these fun questions somewhat weird. Best to go for the next person if you think they find the idea childish.

42. Real talk, do aliens exist?

Why It's Great: One of the most classic conversation topics, but one that isn't asked enough, in my opinion. I try to ask this every time I meet someone new, and it's always gotten me a fun response.

Who To Ask It To: Kids love talking about aliens! They're perfect for asking this, because they all have such adorable responses.

Who NOT To Ask It To: Close-minded people, definitely. It would be awkward if you pose this question to a realist, or even a skeptic.

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

Why It's Great: This is a fun way to explore whether they think the best is behind us or is yet to come. It’s going to be an endless conversation!

Who To Ask It To: Excellent open-ended questions like this can have you chatting for hours with your future wife! It’s never a bad idea to discuss such topics with her.

Who NOT To Ask It To: There's not really a wrong person or time to ask this, so fire away!

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

Why It's Great: This creates a lighter discussion about aging than you would normally come across, which makes it more worth it. Here, you're not thinking about the negatives of getting older but all the things that get better with age.

Who To Ask It To: Oftentimes, couples ask this to each other. You can use the answers to plan an exciting future for you and your partner.

Who NOT To Ask It To: Maybe you should avoid asking this to someone who loves being young. They wouldn't have much to say about it.

45. Would you rather give or get bad advice?

Why It's Great: An interesting way to talk about selfishness and selflessness. It also digs deep into a person's morals.

Who To Ask It To: Friends, naturally. You should also use this time to share some very amusing bad advice stories with your friends, then ask more hard would you rather questions.

Who NOT To Ask It To: No one is a bad target. I'd say everyone wants to receive advice for something, no matter how inconsequential.

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

Why It's Great: Asking a person what they consider the least bad thing may sound counterproductive, but endless conversations were born from picking the lesser of two evils.

Who To Ask It To: A silly way to tease your always-hungry girlfriend is to pose out some interesting questions about food. Make sure to pursue why they chose one over the other!

Who NOT To Ask It To: Someone who's actually experienced this isn't someone you should ask. Drudging up bad memories isn't something you want to do at all.

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

Why It's Great: A challenging but amusing question to answer! This is very open, and can lead to some very deep and novel responses.

Who To Ask It To: Asking a person who loves providing joy will work. They either have an answer thought or, or will form one when you ask.

Who NOT To Ask It To: Someone who'd rather keep the money to themselves. It's not to say they're selfish, but they just wouldn't give you an answer.

48. You have to give a 10-minute speech at a high school. What is it about?

Why It's Great: This encourages you to think about something you'd talk about. Ironically, talking about talking about something can be really interesting.

Who To Ask It To: It might be cool to ask this to your now successful high-school best friend. Reminiscing the good old past is surely a must-have!

Who NOT To Ask It To: Someone who's had a bad experience in high school. Or with schooling in general.

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

Why It's Great: The iPhone or the electric toothbrush? The hot-air balloon or the humble shovel? There are so many options, and each choice could have a significant impact on the world.

Who To Ask It To: Whether your group chooses things that do the most damage to humanity or randomly picks items we use every day, the choices and the reasons will be pretty amusing.

Who NOT To Ask It To: On the other note, it's not advisable to ask this if your conversation partner isn't going to be serious about it. While it could be fun to play around with the answer, it's not gonna be a deep conversation.

50. What's the best conspiracy theory you can make up on the spot?

Why It's Great: Life is full of conspiracies, and once the ball is rolling, you can really end up in some pretty bizarre and hysterical places. Perfect if you'd like to be surprised by the answer.

Who To Ask It To: This one works best with a group since conspiracy theories are great to build off one another.

Who NOT To Ask It To: An actual conspiracy theorist who does it only for malevolent reasons.

51. Are people ethically obligated to improve themselves?

Why It's Great: As long as their behavior doesn't affect other people, is it okay for people to be terrible if that's what they want? Of course, that's rare, and most guys want to know how to be a better man. Use this to find out if they believe we need to constantly be improving.

Who To Ask It To: Use this question to bond with someone who has strong belief principles. They probably have a lot to say about this deep topic.

Who NOT To Ask It To: You'd probably get a dull response from a person who's perfectly content with themselves. It's probably best to choose another question for them.

52. Should there be limitations on the right to free speech?

Why It's Great: This can be a little controversial, but such conversations are where discussions can truly come alive. If you're not afraid of what you'll hear, this is definitely something you should ask.

Who To Ask It To: Friends whom you've not asked this question yet. As long as you both know it's hypothetical, no matter the answers, it will only be interesting and not frightening.

Who NOT To Ask It To: A person in a state of power doesn't really need to question their right to free speech, let alone setting limitations for other people. You should avoid asking this to them.

53. How conscious do you think animals are?

Why It's Great: Pondering the mysteries of the world is about as deep as a question can get, and that's why you should ask them. How else would you come to a conclusion without it?

Who To Ask It To: People who like philosophical questions will get a kick out of this. You can say this to bond with them and get them talking about their ideas.

Who NOT To Ask It To: You can maybe avoid saying this to a person who doesn't like animals. They may not have much to contribute to the conversation.

54. What should be the goal of humanity?

Why It's Great: Questions like this and "What's the true meaning of life?" usually don't have black-and-white answers. Everyone has their own perspectives, and why this question will never be uninteresting.

Who To Ask It To: A dreamer, or a visionary, may be the one you ask. The grandest answers come from them, and those are always inspiring.

Who NOT To Ask It To: Not everyone likes discussing questions that don't have a definitive answer. You can choose other questions to bond with them and skip this one for now.

55. Does a person's name influence the person they become?

Why It's Great: It's a riveting topic to discuss, especially if your friend's name is one of the famous meme-worthy names. You have your Karens, Susans and Chads. Thanks to the internet, lots of names have connotations.

Who To Ask It To: People you know the names of, naturally. You won't be able to hear and understand their thoughts on this if you don't know, right? If they're perfectly cool about their name, this one will definitely make them laugh and get them talking.

Who NOT To Ask It To: People who dislike their name or have been given the wrong rep for it.

56. What do you think would be humanity's reaction to the discovery of extraterrestrial life?

Why It's Great: It makes you wonder about the endless possibilities of what's out there and how they'd react to it. Endless scenarios have been imagined of this, and it's just not enough.

Who To Ask It To: People who love astronomy and extraterrestrial theories would love this topic. You'd probably learn a lot from the stuff they've read or watched about aliens, so listen up and ask follow-up questions to keep the conversation fun.

Who NOT To Ask It To: Skeptics and people who don't believe in aliens.

57. Is chivalry still relevant today?

Why It's Great: This one's incredibly topical, no matter the sex of the person you ask. Do guys still believe they should be chivalrous, and do girls appreciate someone who is?

Who To Ask It To: Anyone, but chivalry is most often applied to men. A real man wants to look his best, and that includes his behavior and manners. Do alpha males, gamma males, omega males, etc., have different ways of showing chivalry? With this query, you can find out!

Who NOT To Ask It To: You can steer clear of this question if you come across a hardcore feminist. They're going to have a lot to say about it, but it can put you in a negative light for them.

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

Why It's Great: If you want to learn more about what made a person the way they are today, this is the intriguing question to ask. It's sure to be something that has helped shape who they are and where they are in life.

Who To Ask It To: Someone you look up to or someone you respect. They must all have been shaped by something, after all.

Who NOT To Ask It To: People you don't respect one bit. If they aren't an especially respectable person, what could you possibly want to know about what they learned?

59. What do you value most in a friendship?

Why It's Great: It teaches you about the kind of friend they are and the friend they want to have. It can also inspire you to be better or feel better about what you already are.

Who To Ask It To: Your partner and friends are the most obvious answers. You want to know what they consider to be the best traits in a pal, and you'd want to have those traits to keep them in your life.

Who NOT To Ask It To: You probably would regret asking this one to a person who likes to be alone. This doesn't mean introverts, but rather those who much prefer not to have friends if they can.

60. Would you rather be 100% confident in who you are or be 100% satisfied that you're with the right person?

Why It's Great: With this, you'll be sure what they want in life. Loving yourself, being confident, and having self-respect is extremely important, but is it as important as knowing you're with the right person?

Who To Ask It To: Barring a few exceptions, there are plenty of people you could ask.

Who NOT To Ask It To: The first time I used this, I completely messed it up. That's because I asked someone single. They got offended and refused to answer. You should only ask this question to someone confident enough to admit that they're single and won't get mad when someone points it out.

61. Is love a choice or a feeling?

Why It's Great: Whatever her opinion is, talking about love with your crush is a great way to get her to think about those romantic emotions. If she's thinking about love and relationships while you're around, perhaps she might see a connection.

Who To Ask It To: You can ask your couple of friends about this and discover what they deem love as. Be as open as you can and ask a few follow-up questions as well.

Who NOT To Ask It To: When you fall in love, it's like you're flying, and you don't ever want it to end. If you find a person who's completely smitten, it's best to avoid this one because it will only make them question their adventures on cloud nine.

62. Do opposites attract, or are like-minded people more compatible in relationships?

Why It's Great: This one is a sure winner for spawning deeper conversations. Even with just two choices, there are tons of ways you can explain it or against it!

Who To Ask It To: You can ask anyone regardless of relationship status, but you should really be asking couples this. They're the ones in the relationship, so they must have some beliefs backed up by experience.

Who NOT To Ask It To: Someone who's going through a break-up wouldn't enjoy this question. It will just remind them of how things didn't work out with their ex.

63. Should you change yourself for someone you love?

Why It's Great: An interesting moral quandary that almost always has a deep and well-thought answer. Need I say more?

Who To Ask It To: You can ask this directly to your crush. They'd think long and hard about it, I assume. A simple answer really doesn't do this question any justice.

Who NOT To Ask It To: If your friend is perfectly content with who they are, it would be a waste to ask this one. You know what they'd answer with.

64. Can you love more than one person at the same time?

Why It's Great: It tells you a lot about what the other thinks is okay in romance. Be sure to follow up this question with, "Would you love more than one person at the same time?"

Who To Ask It To: People who are really open about their love lives will get a kick out of answering this one. They'd share valuable insights and tips for handling it.

Who NOT To Ask It To: Cheaters. Bringing that up will only allow them to make shaky excuses.

65. How do you know you are in love?

Why It's Great: Rather than talking about being in love, talking about knowing you are in love can be an interesting change.

Who To Ask It To: Your crush would be at the top of your list to ask this question. Are there telltale signs? If she starts rattling off signs and you're ticking all the boxes, you're going to want to know how to tell a girl you like her.

Who NOT To Ask It To: It would be weird to ask your friends this, especially if you've had some history together. It's best to choose other people to ask.

66. Do you usually remain friends with your exes?

Why It's Great: Even if you know they'll respond with yes or no, this gives them the floor to explain more about why.

Who To Ask It To: If you want a certain girl to be your girlfriend, you'd want to know if they are comfortable being friends with their ex. You can then decide if that's something you're okay with, should you pursue the relationship with her.

Who NOT To Ask It To: Do you have an ex you desperately want to get off your back? Make sure you don't ask them this. It will only make things more difficult for you.

67. What will your future self remember about you now?

Why It's Great: This is a smart way of getting to know her through her own eyes. She'll express how she sees herself at that very moment. If she says anything negative, make sure to swoop in with compliments and make her feel great. A girl likes it when her value is reinforced and appreciated by someone, so let that someone be you.

Who To Ask It To: Besides your potential girlfriend, you could also ask someone who influences you a lot. If you have an authority figure in your life that you want to emulate, use this to find out what they're most proud of about themselves.

Who NOT To Ask It To: Asking a person with a mental health problem wouldn't be a good idea because they might feel uneasy about finding something they're proud of.

68. Do you believe it's important to always celebrate relationship milestones?

Why It's Great: An important question to ask a potential or current partner, and a great one to ask if you want to know more about what they think. It's very multi-purpose, which is why you can use it over and over again!

Who To Ask It To: You can ask this to your potential partner. It would be good to know what she likes so you could decide if you're good with it too.

Who NOT To Ask It To: Older people squirm when younger people talk about their milestones and anniversaries. Maybe you can choose other questions for them.

69. What's the most romantic thing you've ever done?

Why It's Great: It's good to ask this one so you get clues on what your crush finds romantic. If you ever get an opportunity to show her how you feel, you can bring a bit more personality to the table than by inviting her on a simple dinner date. Coming up with unique and cute date ideas is a great way to show her how much you care for her!

Who To Ask It To: Your crush will enjoy answering this question. Follow up by asking what she likes to do!

Who NOT To Ask It To: If there's a friend of yours who likes you, yet you don't feel the same for them, it's probably best that you steer clear of questions like this.

70. How do you make friends?

Why It's Great: This is a simple question that nonetheless never fails to get people to talk. Even classic questions that you've heard from someone else can take a different meaning depending on who you're answering.

Who To Ask It To: When you ask your crush about how you make friends, you'll learn how they make connections and what sides of them they want other people to know them for. And if you want to get closer to them afterward, some funny pick-lines make the best conversation starters.

Who NOT To Ask It To: If there's a person in the group you don't really feel like talking to, maybe you can avoid this question.

Ultimate List of Deep Conversation Starters


Deep Conversation Starters for a Girl

Getting into a good conversation doesn't always start naturally. You might go through a bit of awkward silence before you come across a topic that both of you will like. Still, when you do come across something both of you will enjoy, you'll end up talking for a long, long time.

Finding the right deep conversation starters isn't always easy, but that's why I'm here to help you. These deep questions are great as a general conversation starter, segueing into other, more involved topics. While they can be asked of anyone, they're especially good to ask girls, so I suggest saving them for a girl interested in a more meaningful talk.

  • What are some random fun facts about you?
  • Where have you traveled?
  • When do you feel most out of place?
  • What small things brighten up your day?
  • Where's the best place to have a picnic?
  • What does a typical day look like for you?
  • What is something you want to learn how to do?
  • What is your biggest pet peeve?
  • What do you do to unwind?
  • What's the best meal you've ever had?

Deep Conversations Starters for a Guy

Guys may sometimes have difficulty expressing their thoughts without the right prompt. There are exceptions, but a lot of guys don't really tend to talk very much without being asked specifically.

That's why you should use a few of these conversation starters: it guides them into talking about something you want to talk about. Not only will you have allowed them to express themselves, but you will have also learned more about who they are. It's a win-win situation when you get him talking, for sure.

  • Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?
  • What is the greatest accomplishment of your life?
  • What do you value most in a friendship?
  • What is your most treasured memory?
  • If you could have three wishes, what would they be?
  • Who was your favorite cartoon character when you were a kid?
  • What does spirituality mean to you?
  • Do you believe in giving people second chances, and why?
  • How would you describe your first crush?
  • What are your favorite hobbies?

Deep Conversation Starters for Couples

Some long-term couples often say that they were able to stay together for so long because their partner is the easiest, most comfortable company in the world. The conversation comes naturally because they've tackled every which way a concept or an idea can go.

When you're in a relationship, and you want to express your deep ideas, you can use these conversation starters for couples to open up a few topics that you feel both of you will enjoy talking about. They will strengthen your bond even more and help keep the spark alive.

  • What experiences have made you who you are today?
  • What is your Achilles heel (your weak spot)?
  • When did you last cry in front of another person? By yourself?
  • If you could choose, would you have chosen to be born a girl or a guy?
  • Have you ever felt very strongly about something and then eventually changed your mind about it?
  • What do you think is your best quality?
  • Do you want to have kids?
  • What do you think is my best quality?
  • What’s a deal-breaker for you in a relationship?

Deep Conversation Starters Infographic

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Downloadable and Printable List of Deep Conversation Starters

Here is a downloadable and printable jpg/pdf list of deep conversation starters (right-click the image and select Save Image As...):

Frequently Asked Questions

Deep conversations can get tricky, especially when you dig into the nitty-gritty and get personal. I bet you have some questions about them, and how to keep the conversation going. So, I've answered some of the most frequently asked questions to help you have smooth, natural discussions - this will help you keep the ball rolling.

How to start and have a deep conversation?

Many of the best discussions are unplanned and happen organically, but starting one can be difficult. Questions get you started on a good path, but you should be aware of the following before you begin:

  1. Think about who you are talking to. When you think about how to start a conversation, particularly how to get into some deep topics, the first thing to consider is your conversation partner's relationship with you. If they're your romantic partner, you may feel any subject is open, but a colleague or acquaintance may need some limitations. Be careful not to push too hard, as it could make someone feel uncomfortable. Also, don't just focus on your interests but the other person's as well.
  2.  Choose the right place to have a serious and long talk. Some venues lend themselves to intimacy: cafes, museums, and the right bar. Other places, not so much, like rock concerts or a boardroom right before a meeting. If you want your conversations to be successful, pick a place where the setting encourages a good, long chat.
  3.  Choose the right deep conversation starter. Once you've settled on points one and two, choose the best deep topics you want to discuss. If you talk about a particular subject and it doesn't seem like they're interested, change the subject. Sometimes, topics work, and sometimes they don't. It can depend on their mood and how willing they are to talk about certain things. Some people don't like talking about their childhood, for example, but would love to talk about the future. So, it also helps to keep in mind what they'd be open to talking about.
  4.  Share your own opinions, listen, and ask more questions. Over the course of the conversation, you'll be asked to answer your own questions and share your opinions as well. Make sure to answer these honestly and openly. Remember, conversations aren't interviews! Next, make sure to listen well; otherwise, there's no point in asking questions. Finally, make sure to ask follow-up questions, so the conversation can naturally progress.
  5.  Have fun, and don't get heated. When you start talking about deep topics, there's always the potential for heated opinions to come out. You don't have to agree with them, and it's okay to debate, but try to avoid becoming offended or talk in an offensive way. The best way to avoid offense is to keep things light, but still meaningful. Choose funny questions that will keep things playful and keep your talks from getting too serious.

What are the benefits of asking deep questions?

Asking deep questions creates an opportunity to have those deeper discussions where you get a real insight into a person, more than just ordinary, daily conversations. It's a great way to create a stronger bond, cement solid friendships, and create intimacy.

How do I keep up meaningful conversations with a girl?

It's always about asking the right questions and not pushing any boundaries. Part of having these intimate conversations is making sure the other people involved are comfortable with whatever is being discussed. That can be as easy as simply asking them if they're okay answering such questions or paying attention to their body language or their answers. If they don't seem engaged in the topics you're bringing up, it might be time to change the subject.

Do introverts like deep conversations?

They do, with the right people. You have to build a certain level of trust before introverts will open up. Of course, some are happy to have deep conversations that aren't too personal in nature. You'll just have to test the waters and see which topics they're okay with.

How do I get our relationship to a deeper level through chatting?

To create more meaningful and deeper relationships, you have to build trust. You have to show that you also trust them by opening up and sharing your deepest thoughts and feelings. You can't expect people to simply open up to you straight away. For some, it takes time. You just have to show you're willing to put in the effort and that, at the end of the day, you're someone worth trusting and having a deeper relationship with.

More Deep Conversation Starters

Deep conversations don't start and end with the questions above. There's plenty more where those came from.

  1. If you want to truly dig into the meaning of life, try a few existential questions. It's sure to get some fascinating conversations going!
  2. On the other hand, if you just want to start a great discussion giving people difficult and interesting choices, try a few of our would you rather questions.
  3. Ponder the same questions that ancient philosophers like Plato and Aristotle did with these philosophical questions. They're compelling to think about and usually spark great, deep conversations when asked.