Deep conversation starters are truly powerful.

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 Marriage.com, iHeart Media, Elite Daily, and many more!

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

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Contents

10 Deep Topics to Start a Conversation

We all get sick of the everyday chit-chat, so how exactly do you start deeper, more fulfilling discussions?

The answer is in having great questions to initiate great conversation topics. Use deep conversation topics to get to those more interesting discussions everyone would rather be having.

Here are 10 deep conversation starter topics:

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

Immediately, people give deep thought to a question about their struggles. You've introduced a topic that has everyone thinking back to their childhood or when they were teenagers for memories to share.

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

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? Would it be a day spent with loved ones and old friends?

3. Can a positive outlook make any situation better?

Does positivity really help? You'll get a great debate going between the optimists and the pessimists about everyday life and whether a positive outlook has an impact. If you have follow-up questions, you can create meaningful discussions on this topic!

4. 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?

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? To have deeper conversations, you have to also share your experiences. It's about swapping stories and digging for more details by asking the right questions.

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

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. Honest, responsible, messy. Are they simply just sharing their opinion about themselves, or do they really believe it's how their friends and family see them?

6. What age do you feel on the inside?

Are they older than their years or still a child at heart? Talking about age and life can be a philosophical and meaningful conversation. It can be a profoundly deep exchange. What age is best to feel on the inside anyway?

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

No one likes to quit, but is quitting sometimes what's best? If so, when? To some, giving up is about no longer making excuses. They've realized there are more productive, efficient, and effective things they could be doing instead. It's a well-thought-out choice they make.

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

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.

9. What makes everyone smile?

It could be a person, an activity, or a TV show, among other things. It's thought-provoking questioning, one you've really got to think deeply about. What does make everyone smile?

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

A chance to compare the wisdom passed down from the last generation. They never had Twitter and other social media back then. Did that have an impact on the lessons they passed down?

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10 Best Questions For A Deeper Connection

Once you know the best conversation starters, you can consider which questions work best for you to create a deeper connection. Knowing how to define your list of personal values will help you keep a conversation going that's full of meaning and exposes who you really are.

Here are the 10 best questions for a deeper connection:

11. What will you fight for until the day 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. Turn casual friends into lifelong ones by building a solid connection.

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

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. This would start a good conversation about work experiences. Connect by talking about your careers and values.

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

No place is perfect, but everyone has an ideal location of where they'd rather live. Whether it's somewhere with warm sunny climates or snow frost on the windows every morning, personal questions like this can say something about a person. This subject also opens the door to talk about cultural differences in various places.

14. Would you rather be hated or forgotten?

We live in a time full of celebrities and the constant, always present social media. Imagine going through some of the experiences they have and having actual anti-fans. How important is it to someone to be remembered and immortalized? A good connection can be made with someone by sharing opinions and debating.

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

Would the world be better without the internet? Without consumerism? Without free speech? This discussion can lead to some very deep and sometimes controversial exchanges. But what's a better way to build a deep connection with someone than getting engrossed in meaningful conversations together.

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

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.

17. Do you believe in Karma? Why?

Karma is a concept deeply believed by some and entertained or ignored by others. Regardless, everyone has an opinion, and that opinion deeply influences how someone may act. Asking deep personal questions will give you insight into someone.

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

Guys want to know how to be a better man, but many don't know where to start. Asking questions like this can really make you think about what exactly it is you want to try and achieve. The challenges can be something you could consider doing together to help you bond.

19. Who do you aspire to be more like?

Who we admire is crucial to who we become. 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. It's a bonus when great conversation starters make you reflect on yourself.

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

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

10 Deep Conversation Openers to Ask a Girl

Knowing the best questions to ask a girl is the right way to get her to share deeper, more personal thoughts with you. If you want her to take notice and remember your conversations, be prepared with some deep questions to ask a girl.

Here are 10 deep conversation starters to ask a girl:

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

Make her choose the one thing she needs to do to consider her life a success. It'll tell you volumes about what her values are. This is a great example of good conversation starters with girls that will provoke profound discussions.

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

A chance here to be a little self-critical and then consider the nature of that flaw. It's good to have interesting conversation starters like this one if you're out with her having dinner.

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

We all have first love stories, whether beautiful, tragic, or banal. It's not just one relationship expert, but a few that argue first love stick with people and never die. Bustle.com also says first loves have a huge impact on your future relationships.

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

The term "things" is intentionally vague, so she can choose objects, emotions, experiences, or whatever comes to mind. Good questions for a deeper discussion with girls are open and have the potential to be lengthy.

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

Here you have a chance to start talking about what kind of risks are worth taking. Of course, everyone's idea of adventure is different, so connect with her by having this fun discussion. Think back on childhood memories and compare whether the things you considered dangerous back then would still be hazardous now as adults.

26. What totally impresses you?

Keep her answer in the back of your mind. If you want to know how to impress a girl, it's important to pay attention to the things she says. If you ever get romantic feelings for her and want to take things to the next level, at least you already know what things impress her.

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

A meaningful connection can be made when you start opening up to someone about your goals and dreams. You're shrinking the size of the field to six months to get a genuine and clear answer. See if you can't help her along the way. It'll make her happy, and she'll appreciate the support.

28. What makes you feel proud?

Is it family? Is it her career? Is it a talent? Regardless, it's sure to be an interesting subject matter to discuss. Watch her beam with pride as she talks about things that give her a strong sense of self-worth.

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

This is a great way to find out what kind of work she truly loves. 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. Working hard and loving every minute of it sure to be a story about success or growth.

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

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

10 Deep Communication Starters for Couples

For deeper communication with your partner, it's great to tailor your questions to them. You can use conversation starters for couples that focus the attention on important topics.

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

Here are 10 deep conversation starters for couples:

31. Is competition good for us?

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? You 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 they need.

32. How would you hate us to be described?

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

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

Many couples' arguments aren't about one partner hurting the other; they are about one partner fighting their own demons and projecting outward. This discussion allows you to open up that can of worms in a thoughtful and non-confrontational way. You want to support your partner and show them that they are loved no matter what. And that sometimes, they don't give themselves enough credit.

34. 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? Are you ready for them to take the spotlight, or would you rather have some of it too?

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

There are different ways 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? You don't need a relationship coach to tell you that partners should see each other in their futures for a romantic relationship to be successful.

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

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

37. What are you most afraid of losing?

Is your partner materialistic? This opens up a discussion about what's most important in life. Is it the possessions we own or the people we love? You can add a challenge to the question and actually make her choose a material object. Just to keep things interesting.

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

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. A key to keeping a strong relationship is making sure you're on the same page regarding crucial and serious decisions.

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

Relationships thrive on truthfulness. But is there a situation where a little strategic lying is a benefit? Where is that line? And how forthcoming is your partner about those sorts of situations?

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

It can feel safe to pretend problems aren't there, but this conversation starter deeply lets you discover what makes your partner dissatisfied with your relationship. It's great to know where there is room for improvement. The only way you can fix issues is by knowing what they are.

10 Deep But Funny Questions to Initiate a Conversation

When conversations start to feel a little heavy, look for topics that lead to good, interesting chats instead of the everyday small talk. Try funny conversation starters where the questions lead to deeper discussions that are still enjoyable, entertaining, and meaningful.

Here are 10 deep but funny conversation starters:

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

How creative are your conversational partners? This is a funny get-to-know-you inquiry about the world you would build for yourself if you could. Virtual reality or not, would it be a dystopian or fantasy setting? What's the environment and the culture like? The possibilities are endless!

42. Real talk, do aliens exist?

One of the most classic conversation topics. Try springing this to start controversial and often animated discussions. Dive into the world of conspiracies.

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

This is a fun way to explore whether they think the best is behind us or yet to come. While some of our greater memories might influence us to choose to relive those moments in the past, the possibilities of the unknown ahead is an intriguing option. Excellent open-ended questions like this can have you chatting for hours.

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

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

45. Would you rather give or get bad advice?

An interesting way to talk about selfishness and selflessness. It also digs deep into a person's morals. Use this time to share some very amusing bad advice stories, then ask more hard would you rather questions.

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

A silly way to tease out some interesting answers. Make sure to pursue why they chose one over the other. To really get to know someone and have prolonged, fun, and meaningful conversations, you have to get deeper. The only way to do that is to ask more questions!

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

A challenging but amusing question to answer! It's a chance to let your conversational partner be a little creative and also show their charitable side. This is very open and can lead to some very deep and novel responses that will initiate debate and lively discussions.

48. You have to give a 10-minute speech 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. Is the speech going to be about life lessons, something serious, or something light and fun?

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

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

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

Life is full of conspiracies. 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.

10 Deep And Thought-Provoking Icebreaker Questions

Starting topics with thought-provoking questions is a bold move, but it can pay off. Plenty of people out there are thrilled when you open with big talk instead of small talk. After all, life is short, so why beat around the bush with softball questions? The best way to get to know someone is to break the ice by exploring thought-provoking topics and fascinating ideas together.

Here are 10 deep and thought-provoking icebreaker questions:

51. Are people ethically obligated to improve themselves?

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. But is it really by personal choice, or do we feel ethically obligated to improve ourselves?

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

Should people be allowed to express themselves in any way they see fit - even if it's hateful? What is okay to be said out loud and what's not? Many people go through life walking on eggshells to make sure they only ever say nice things. Should they not limit themselves and just say what they're truly thinking?

53. How conscious do you think animals are?

Is your dog an accomplished philosopher who lacks the ability to communicate his brilliance?

54. What should be the goal of humanity?

We should probably get that figured out. Is it about the evolutionary road of humankind? Thought-provoking topics are often philosophical and get the wheels turning in our heads. Questions like this and "what's the true meaning of life?" usually don't have black-and-white answers. Everyone has their own perspectives.

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

You have your Karens, Susans and Chads. Names that have gotten famous because of memes. Thanks to the internet, lots of names have connotations. Does the name shape someone, or does the person become the name intentionally?

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

What would that first day look like? How about a week? A month? A year? Life will be forever changed, surely. Whether people have negative or positive reactions depends on how they picture aliens to be.

57. Is chivalry still relevant today?

The general sense of chivalry is courtesy. Traditionally, it was a quality held by knights and noblemen where they would offer courage, honor, and protection to women. But, what does it look like with modern gender roles? Has our ideas of what chivalry means changed over time? Do alpha males, gamma males, omega males, etc., have different ways of showing chivalry?

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

Here, you are looking to discover what wisdom your conversational partner learned either from family growing up or from their own personal experience. It's sure to be something that has helped shape who they are and where they are in life.

59. What do you value most in a friendship?

You want your friends to be honest. They should be dependable and loyal to you. How they feel about you should be clear, and they should be accepting of who you are. Are these the essentials for a successful friendship? And what do you value most?

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

Loving yourself, being confident, and having self-respect is extremely important, but is it as important as knowing 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.

10 Deep Questions to Get Acquainted with Your Crush

If you want your crush to realize you're more than just a handsome face, then you need to follow up your best pick-up lines with something that will get her talking. That's where the best questions to ask your crush come in handy! You've broken the ice, so now get better acquainted.

Here are 10 questions to know your crush better:

61. Is love a choice or a feeling?

Or somewhere in between? Perhaps there's another option - it's a decision. Whatever her opinion, 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.

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

Relationships are built on compromise and growing together. You'll need to make adjustments so that you and your partner can fit together better. Many changes occur naturally throughout a relationship. It will be interesting to know what your crush would be willing to do for the sake of someone she loves.

63. Should you change yourself for someone you love?

What would they do in that situation? It's good to have deep and meaningful conversations with someone you have feelings for to establish compatibility in your values. Before you dive right in and start anything too serious, make an effort to get to know her really well.

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

What would they do in that situation?

65. How do you know you are in love?

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. Turn that friend into your girlfriend.

66. Do you usually remain friends with your exes?

Some people would rather just move on and never look back, and others would like to salvage anything they can so their ex remains in their life, even as friends. It's ultimately an individual choice. If she is still close with her ex, it may be a smart idea to find out if there is still a spark that may flame up at any moment. It might give you a clue to where you stand and what your chances are if you want to take things to the next level.

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

This is a smart way of getting to know her more deeply 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. Let that someone be you.

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

In relationships, it's important both parties feel appreciated, loved, and celebrated for their achievements. But what about the achievements you accomplish together. Saying "I love you" for the first time, meeting each others' parents, anniversaries, and so much more. Are these all worth celebrating?

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

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 a simple dinner date. Coming up with unique and cute date ideas is a great way to show her how much you care and want her.

70. How do you make friends?

Are there such things as pick-up lines for friends? Some funny pick-lines make the best conversation starters. Of course, you're simply using this line of questioning to get to know your crush more deeply. What are the things she appreciates in others, and what does she look for in the people she gets close to?

10 Deep First Date Questions To Start A Conversation

Maybe you don't want to waste time, and you want to know, right here and right now, if your crush is the real deal. No need to beat around the bush; use first date conversation starters. They're a fantastic way to get those important talks going during your first date so you can know right away if you guys can go the distance.

Here are 10 deep first date conversation starters:

71. What are some random fun facts about you?

Some people find it really easy to share things about themselves and open up for a deeper connection. Others, it takes a bit of effort. So while you're on your date, take advantage and ask the right questions to get her to open up to you. This question is a perfect start! Asking your date about facts about herself will teach you things about her you likely never knew.

72. Where have you traveled?

Which place has been their favorite? If your date hasn't been overseas, you can ask about where she'd like to travel instead. Everyone has areas they'd like to visit. Whether it's exotic India or tropical Fiji, it's good to talk about preferences to better get to know each other.

73. When do you feel most out of place?

Feeling out of place could be her being somewhere and feeling like she doesn't fit in, or it could be a scenario where she felt excluded from something. Whatever it is, these situations can make you feel unwanted, uncomfortable, and sad. It's good to know what may trigger this feeling with your date, so you know how to always make her feel like she belongs... with you.

74. What small things brighten up your day?

What tiny joys make her smile? Keep this information handy because it's sure to strike some great ideas for later use. When you want to brighten up your date's day, think back on her answers. She'll appreciate the fact that you were listening and that you remembered. It might even inspire some new romantic things to do!

75. Where's the best place to have a picnic?

What about the worst place? If you've ever thought about having a picnic with your date, this will tell you where to have it and where to avoid. She might like the idea of a beach picnic, or she might prefer a hike up a mountainside where the reward on top is delicious food.

76. What does a typical day look like for you?

Start to finish, let's hear it all. Get deep with your date and talk and compare your lives. Talk about family, your jobs, your pets, your friends. The topics are endless. The more you get to know, the more you understand each other and grow more intimate.

77. What is something you want to learn how to do?

Creative hobbies are always an amusing subject to talk about, but this particular question has her talking about the things she wishes to learn. If she mentions stuff you know how to do, perhaps it's an opportunity for you to show her some of your knowledge and skills. It's a great way to get some more one-on-one time.

78. What is your biggest pet peeve?

Discuss some of the things that annoy your date. It's normal to talk about all the positive things but mix it up a bit by dragging in topics of annoyances. Everyone has a pet peeve. Understanding hers can improve your relationship.

79. What do you do to unwind?

There are a lot of different ways that people relax and unwind. She might teach you about the importance of practicing mindfulness and her stress management routine that you could use too.

80. What's the best meal you've ever had?

Hopefully, it's something you can cook, and you make it up for her. Impress her with your cooking skills because a woman loves a man who knows his way around a kitchen. It's a very attractive quality that speaks volumes about maturity and that you can take care of yourself.

10 Deep Questions to Make the First Move Over Text

Are you trying to get to know someone over text? These excellent text conversation starters are great for getting people to open up. Next thing you know, you've learned way more than you expected, and it's already three o'clock in the morning. As they say, time flies when you're having fun. So move over phone calls; it's texting time.

Here are 10 deep text conversation starters:

81. What do you like but are kind of embarrassed to admit?

A guilty pleasure could be anything from the cheesiest TV show to the raunchiest books. While some guilty pleasures aren't as embarrassing as others, it's an enjoyable subject to talk about. You might laugh at each other's answers. The best part is that you don't feel as embarrassed admitting to these things as you would if you were face to face because it's over text.

82. What TV series do you keep coming back to and re-watching?

Talking about things you find entertaining is a good way to get to know each other. She might introduce you to a TV show you've never heard of, or you might be able to share one you've loved for years. Part of getting to know someone and building a more intimate relationship is exchanging even the small things that bring your life pleasure.

83. Before you make a call, do you rehearse what you are going to say?

Will she willingly admit it? Do they have a voicemail ready in their head? This is exactly why you should always be prepared with topics that will start interesting conversations

84. What's the strangest phone conversation you've ever had?

Hopefully, the strange phone call is something she can laugh about now. Find out what it was that made it odd, so you don't ever cross that line. Was it one of those scam calls? Those can be terribly annoying.

85. How well do you cope when you don't have your phone with you for an extended period of time?

There are billions of smartphones out there and phone addiction is real and more common than you may think. Healthline.com says you can also go through withdrawal symptoms, like irritability and anxiety, if you don't have your phone! Hopefully, your crush isn't this bad.

86. What took you way too long to figure out?

Are they embarrassed about it? Expand this discussion onto things you might know, but she doesn't, and vice versa. Test each other's knowledge on unique trivia! That's always an enjoyable way to prolong conversations.

87. If you could stop time, what would you do?

This is an interesting thing to talk about because the possibilities of where the discussion could lead are endless. You get to learn a lot about her as well with her answer. Like whether she has a mischievous nature or whether she'd use the stopped time to help people in need. Follow up with, "What if they could speed up time?"

88. What is the best advice you've been given?

Everyone has pearls of wisdom that are handy when you least expect it. Usually, these pieces of advice and wisdom come from heartfelt quotes and lessons shared that have been passed on to others. Knowing some good quotes about strength and being strong during hard times are always great to have.

89. What's the worst movie you've ever seen?

What didn't they like about it? The subject of movies is a great way to see if your taste in films matches. Movie dates are always fun and exciting to have, but the choices on what you're going to play matter a lot. Find out the worst, but make sure to find out the best movies as well so you know for future reference.

90. What's the best book you've read?

You may think this is a flat subject matter, but it's a much more personal question than asking about the weather. If she's a book lover, you're inviting her to share a deep part of herself with you. Give her a chance to share her enthusiasm. If there's been a movie made, start a debate on which was better. Of course, any book lover will tell you it's always the book, but you never know. Some movies get it right.

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...):

How to Start and Have a Deep Conversation

Allow the topics to flow naturally and take their course. Many of the best discussions are unplanned and happen organically. Questions get you started on a good path.

Here's 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, particularly how to get into some deep topics, the first thing to consider is your conversation partner's relationship with you. If they are your romantic partner, you may feel any subject is open, but a colleague or acquaintance may require some limitations. Be careful not to push the lines of intimacy 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 the intimacy: cafes, museums, 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 chat.

3. Choose the right deep conversation starter

Once you've settled points one and two, choose the best deep topics you want to discuss. If you attempt a particular subject and it doesn't seem like your conversational partner is interested, sway the discussion elsewhere. Sometimes, topics work, 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.

4. Share your own opinions, listen, and ask more questions

In the course of conversations, you will be called upon to answer your own questions and share your opinions as well. Be sure to be forthcoming and as open as the other people. Remember, conversations are not interviews. Make sure to listen well; otherwise, there is no point in asking the questions.

To push forward from one subject to another and to dig deeper, ask follow-up questions.

5. Have fun and don't get heated

When you start on deep topics, there's always the potential for opinions to get controversial. You don't have to agree with them, and it's okay to debate, but try to avoid becoming offended or offensive.

The best way to avoid offense is to keep things light. Choose funny questions that will keep things playful and keep your talks from getting too serious.

Frequently Asked Questions

Deep conversations can get tricky, especially when you dig into the nitty-gritty and get personal. Here, we've answered some of the most frequently asked questions to help you have smooth, natural discussions:

What are the benefits of asking deep questions?

When you ask more personal questions, you get a chance to learn more about people. Asking deep questions creates an opportunity to have those deeper discussions where you get a real insight into a person. 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 the 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 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.

In Conclusion

By taking your deep conversation starters to the next level and finding the best questions to ask, you're not only learning more about the people you talk to, but you also show that you too are a deep-thinking, interesting, and engaging person. 

Conversations are one of the most important ways we interact. So, whether you are looking to break away from the stale discussions with friends or your romantic partner or looking for creative ways to learn more about others, deep questions to ask will provide you with all you need to have some great conversations.