Deep conversation starters are questions that elicit a deep and engaging discussion.
These questions are often personal and reflect the listener’s interests, or at the very least, the speaker’s obsession.
One of the most powerful ways to connect with others is through conversation starters.
When you ask a personal question and wait for your friend or family member to answer, you will find that it creates a connection between you both.
You’ll start talking about things that you have in common. You’ll find out about their interests, which will make it easier for you to get to know them better.
Deep conversation starters aren’t only useful in developing relationships with people around you, they can also be used to deepen your own knowledge and understanding of something.
In this article, I’ve listed 200+ deep conversation starters on deep conversation topics that are designed to make you more aware of yourself, others, and life in general.
What to say to start a deep conversation?
There are two approaches to starting a conversation with someone. Most people use the “Small Talk Approach,” which involves saying/asking something inane and hoping that it leads somewhere.
This approach is far less effective than what I call “Deep Conversation Starters.” These openers are designed to spark a deep-level dialogue so that you can get to know someone on a deeper level faster.
If you really want to connect with someone new and make them feel special, ditch the small talk.
Instead, ask deep questions that start a meaningful conversation. The other person will feel like you’re listening to them and interested in them — which is good for building a personal connection.
Deep conversation starters
The most difficult part of the deep conversation is often just getting started.
The following deep conversation starters can be used in many situations, with people you’ve just met or with people you already know.
They will help you to start a meaningful and deep conversation, so you can build a deeper connection with the other person and get to know them on a more intimate level.
The words you use in a conversation can help you build a connection right away, or they can make it more challenging.
Here is a huge list of deep conversation starters that will instantly get you on the same wavelength with someone else:
1. “I was thinking about what you said about …”
Showing that you were listening to what the other person said and thinking about it after is a great way to connect. The other person feels heard, and you’ll be able to build on what they said.
2. “I read your article on the five types of people who should never use the word ‘awesome.'”
This shows that you’ve done your research and paid attention to the person’s work — not just their online presence, but also what they care about and how they think.
It makes them feel important while demonstrating that you’re interesting enough to learn more about them.
3. “I liked your thoughts (tweet/post/comment) on the [Topic].”
Praising someone else’s work makes them feel good and also demonstrates that you’re paying attention to them. This works well whether it’s an offhanded comment or something more substantial.
4. “Have you read/seen/listened to … ?”
Following up on a recommendation from someone is a natural way to get back in touch with them. They’ll feel understood, inspired, and connected when you engage with the matters they are deeply interested in.
5. “I liked what you said at the meeting, but I’d like to hear your thoughts on X.”
This is another great way to start a conversation because it opens up room for debate.
People love debating, particularly when they feel like they have an ally in the debate (which you are). Everyone’s inner contrarian likes being asked what they think about something.
6. “So, how did you get into this?”
Asking this question will help you understand where the other person came from and how their life experiences shaped them into who they are today. It also gives you an opportunity to share your own story with them.
7. “What do you love most in life?”
This question will help you learn more about the person’s passions and values, which can help deepen your connection with them.
You might have things in common that you didn’t know about before asking this question!
8. “I was reading this article by _____, and I thought of you.”
This is a good conversation starter because it shows that you were thinking of the other person while doing something else, which makes them feel special.
It also builds on a previous conversation, so it’s easy to continue.
9. “I’m curious about…”
A phrase like “I’m curious about” can open up any topic for discussion. It also makes you sound intellectually curious (which is sexy).
10. “If I could choose 5 people from history to have dinner with, ____ would definitely be one of them.”
This is a great question because not only does it reveal more about the other person’s interests, but it also gives them an opportunity to compliment someone they admire in an indirect way — some of us have trouble doing this directly!
11. “I’m deeply interested in your story…”
You can add in whatever you’re curious about — their job, where they grew up, or how they met their spouse.
This line shows that you’re interested in the other person’s life and want to learn more.
12. “What’s something I don’t know about you?”
This question is simple but powerful because it gets people to open up quickly.
It also gives them permission to share stories from their past or from their lives outside of work, which builds a deeper connection.
12. ” Such a deep perspective! Tell me more…”
This phrase encourages the other person to give more details and tell longer stories, which helps you get to know them better and creates greater intimacy between you two.
13. “I need your help with something…”
When you ask for someone’s advice, help or opinion, they feel needed, valued, and important — a surefire way to build a connection!
14. “I was wondering…would you mind sharing how you made it to this level?”
This is a question that works well when someone tells you something interesting.
It can be used in virtually any context, from learning how someone became interested in their career to hearing about their latest vacation destination.
It shows that you’re interested in hearing more about their experiences and ideas.
15. “What do you think about the whole XYZ controversy?”
Bringing up a controversy related to a topic that you discussed can help create an engaging discussion.
You might be able to learn more about the other person’s opinions while sharing your own thoughts on the subject too.
But remember not to get too serious with this one; make sure it’s appropriate for the environment and conversation before using it.
Deep conversation starters topics to talk about
Here is a list of deep conversation starters topics to talk about:
If you could sum up the universe in three words, what would they be?
What’s your favorite thing about the universe?
If you could ask one question about the universe and get an honest answer, what would you ask?
What do you think about when you look at the stars?
2. Before life
If life is short, why do we do so many things we don’t like and like so many things we don’t do?
How is your life different from what it was one year ago?
What are some of your personal “rules” that you never break?
When do you feel most in control of your life? Least in control?
Imagine if you woke up tomorrow with only the things that you thank God for today. What would be different in your life?
Do you think the purpose of life is to be happy or to push yourself to find purpose and meaning? Why?
5. Best way to die
6. What if you were immortal?
7. What if you had superpowers?
8. If you could travel anywhere in time, where would you go? Would you change anything? Why?
9. What do you think is the meaning of life? Do we have a purpose on this planet or are we just here by chance?
10. Is there an afterlife? If so, what do you think it’s like? Would you want to come back as someone else or something else in your next life?
11. Is reincarnation real? Do souls get reborn into new bodies after death or is it all just a coincidence?
Deep conversation starters for couples
The following are some Deep conversation starters for couples:
1. “What do you love most in life?”
This question will help you learn more about your partner’s passions and values, which can help deepen your connection with them.
You might have things in common that you didn’t know about before asking this question!
2. “What’s the most daring thing you’ve done?”
Everyone has a wild story to tell, even if it is something as small as jumping into the deep end of a pool.
This question will give you and your partner an opportunity to share fun stories while possibly learning something new about each other.
3. “Do you have any regrets?”
While no one wants to dwell on their regrets, it can be helpful to talk through them with someone who loves and supports you.
Sharing your regrets can be a cathartic experience, and revealing parts of yourself that may be considered negative can help grow your relationship by showing vulnerability.
4. “What are your dreams for the future?”
If you’re in a long-term relationship or marriage, talking through dreams and goals for the future can be important in figuring out the next steps together.
Or if you’re dating someone new, it can simply be fun to imagine potential plans with them for the rest of your life.
5. “If you could choose five people to invite to a dinner party, who would they be?”
This question is a fun way to get a sense of what kind of people inspire your partner. It can also give you an idea of the types of values and qualities your partner is looking for in others.
6. “What’s the best compliment you’ve ever received?”
This question can be especially meaningful if it’s something your partner hasn’t told you before.
If the answer involves something that they’re proud of or an accomplishment they’re happy to share, it can help foster a deeper connection between the two of you as well.
7. “What are three things on your bucket list?”
Bucket lists are all about fulfilling personal dreams and goals, so asking this question is a great way to encourage someone to open up about their hopes for the future.
It can also spark ideas for new experiences that both of you would like to try.
Deep conversation starters to build relationships
Here is a list of deep conversation starters for relationships:
1. “I read your article on the five types of people who should never use the word ‘awesome.'”
2. “I’m such a big fan of your work. Is there a book, movie, or TV show you’ve seen and loved recently?”
3. “I’m at [event]. I’d love to know how you found out about it.”
4. “What’s been your favorite thing to do in [city]?”
5. “You seem really interesting. What’s your background?”
6. “What are you working on right now?”
7. “What was the last great book you read or podcast you listened to?”
8. “I love it when people are good at what they do and also nice — like, they don’t have to be jerks just because they’re good at their jobs.”
9. “How did you get into what you do?”
10. “I know this is an unusual question to ask someone at a first meeting, but I’m curious: what do you think about when you have time to yourself?”
11. “[Mutual friend] told me about how much fun she had getting drinks with you.”*
12. “At this stage in our lives why do we think we need to learn and connect more with people?”
Deep conversation starters with a girl
Here is a list of deep conversation starters with a girl:
1. What’s something you always wanted to do as a child but never got to do it?
2. If you could convince everyone in the world to do one thing at one point in time, what would that thing be?
3. Is there something that people consistently ask for your advice on?
4. What’s something you know you do differently than most people?
5. What’s the most sensible thing you have ever heard someone say?
6. What gets you excited about life?
7. What life lesson did it take you the longest to learn?
8. What are you addicted to?
9. When was the last time life left you breathless?
10. If not now, then when?
11. If you haven’t achieved it yet, what do you have to lose?
12. Have you ever (or how often do you) stay(ed) out all night?
13. Would you rather explore the ocean or outer space? Why haven’t you done it already?
14. What is your favorite drink? How many times a day do you enjoy this drink of yours (and would it be more or less if it was free)? Would buying this drink for others make them like you more
Deep conversation starters with a guy
Here is a list of deep conversation starters with a guy:
1. What is your definition of love?
2. What is the meaning of life?
3. If you could choose one superpower, what would it be and why?
4. What are the top three things on your bucket list?
5. If you had to eat the same meal for the rest of your life, what would it be?
6. What do you think about when you daydream?
7. How would you describe yourself in five words?
8. Is there anything that makes you feel invincible?
9. What’s something that’s worth spending more on to get the best? And why?
10. Why do you think some people are attracted to bad relationships, dangerous things, etc.?
11. If all jobs had the same pay and hours, what job would you like to have?
12. What is something that a ton of people are obsessed with but you just don’t get the point of?
13. When was the last time you changed your opinion / belief about something major?
14. Have you ever saved someone’s life or did someone save yours?
15. If you could change one thing from your past, what would it be and why?
16. What is a controversial opinion you have?
Deep conversation starters for texting
Here are some very deep conversation starters over text on online:
1. What’s your biggest dream in life?
2. What made you smile today?
3. you could be any fictional character who would it be and why?
4. If you could go back in time to any period in history, when would it be and why?
5. What’s the most amazing place your eyes have ever seen?
6. If you could learn one random skill, what would it be?
Deep intellectual conversation starters
These are a few of the philosophical deep intellectual conversation starters to ask:
1. What’s the most beautiful thing you’ve ever seen?
2. What do you think happens when we die?
3. What is the meaning of life?
4. Is there a God?
5. What makes a person truly evil?
6. If you could change one thing about the world, what would it be?
7. Do you believe in love at first sight or should I walk by again?
8. If you had to describe yourself as an animal, which one would it be and why?
9. What was your favorite childhood memory?
10. If you could ask any person alive or dead one question, who would it be and what would you ask?
Deep conversation starters for crush
Here is a list of Deep conversation starters with your crush
1. “What would you do differently if you could go back to being 20 years old?”
No one can change the past, but this conversation starter will help you learn more about what your partner’s regrets are and what they wish they would have done differently.
This is a great way to get to know someone and also understand who they are now.
2. “What types of people do you consider yourself to be most compatible with?”
This is a romantic way of asking about your partner’s interests and likes — or dislikes — without prying into their lives too much.
It’s also a good way to get to know them better by learning more about their past relationships and what they learned from those experiences.
3. “How would you like people to describe you when they talk about you?”
This question helps your partner articulate what they really want out of life, which is important information to know if you plan on spending the rest of your life with them! It also gives insight into
Deep conversation starters for best friends
Here is a list of deep conversation starters with friends
1. What were you like as a kid?
2. What’s the most beautiful place you’ve ever seen?
3. What do you think is worth spending extra on to get the best?
4. What’s the most annoying question that people ask you?
5. What do you feel most grateful for in your life?
6. What do you hate about meeting new people?
7. If someone spent a day with you, what would they see you do?
8. What’s your favorite part of a vacation?
9. How did your parents influence who you are today?
10. If time and money were no object, where would you go on vacation?
Deep conversation starters about love
Here is a list of deep conversation starters about love:
1. Why do you think you connect only with a few people in the entire universe?
2. Do you believe the universe brings two people together?
3. Is there such a thing as true love?
4. Is saying “I love you” really the best way to express feelings of love? Or should we say it less often and act loving more often?
5. Is it our destiny to find true love? Or do we just get lucky if we ever find it?
6. Do humans have a purpose in life? Is our purpose here on earth simply to reproduce and pass on our genes, or are we here for something else?
7. Can you ever truly know someone else’s mind?
Or is all communication fundamentally flawed because no one can ever truly understand what another person is thinking or feeling unless they have experienced exactly the same emotions themselves?
8. Do you believe that there is a God who controls everything or do you think that everything happens by accident and chaos rules over all things in the universe?
9. What’s more important: physical beauty or inner beauty?
Deep conversation starters with your girlfriend
Here is a list of deep conversation starters with girlfriend:
1. “What makes you feel safe?”
Everyone has different ways of feeling secure. Some people might feel safest when they’re at home, while others might feel more secure when surrounded by loved ones.
Figuring out how your partner feels the most comfortable can be a great way to build intimacy and trust.
2. “What’s the best thing about being yourself?”
You’ve probably had times when you didn’t feel like yourself, but what are some of the best things about your partner?
By asking this question, you’ll make them reflect on their own positive qualities and traits that make them who they are — and hopefully get them to share these positive attributes with you!
3. “Who is your hero?”
Maybe it’s a celebrity or maybe it’s someone close to them — either way, learning who your partner thinks is a hero is another great way to get insight into their values and build intimacy.
Here are some more deep conversation starters for dating to ask your girlfriend:
1. What are you most grateful for?
2. What makes you feel the most alive?
3. If there was one thing about your life that you could change, what would it be?
4. What makes you feel vulnerable?
5. What was your most formative/impactful life experience, and why?
6. What is your favorite color, and why?
7. Do you think things happen for a reason, or do we just find reasons after they happen?
8. How would you describe your perfect day?
9. Have you ever made a really big mistake, and if so, how did it impact your life going forward?
10. Do you believe in love at first sight, or should I walk by again?
Deep conversation starters with your boyfriend
Here is a list of deep conversation starters with your boyfriend:
1. If you could have one superpower, what would it be and why?
2. What TV show title best describes your life?
3. Who’s your go-to person when you’re feeling down?
4. What’s the most spontaneous thing you’ve ever done?
5. What is the most important thing you want to accomplish before you die?
6. What is your favorite book and why?
7. Do you think the glass is half full or half-empty?
8. What would be your ideal way to spend the weekend?
9. If you could visit any place on earth, where would it be and why?
10. If you could go back in time, what year would you travel to and why?
11. What motivates you to work hard?
12. What are three things on your bucket list that you plan on doing soon?
13. What’s your favorite thing about yourself — physical or otherwise?
14. When was the last time someone made a real effort to get your attention — what did they do and how did it make you feel?
15. What is one thing that has made a significant impact on who you are as a person today?
Deep and meaningful conversation starters
Here are some deep and meaningful conversation starters:
1. “What’s your earliest memory?”
2. “What’s one thing that makes you feel alive?”
3. “What is your spirit animal and why?”
4. “What are the three most important things everyone should know about you?”
5. “What are your views on cheating and monogamy?”
6. “How do you think people perceive you?”
7. “What do you feel most deeply guilty about in life?”
8. “Who do you feel most connected to in life?”
9. “Would you ever take back someone who cheated on you if they promised to never do it again?”
10. “Which role models have influenced you the most in life and why?”
11. “If money didn’t matter, what would you do with your time?”
12. “Have you ever felt like an outsider? When and where was this? How did it feel being an outsider in this situation?”
13. If a genie granted you three wishes right now, what would you wish for? Why these wishes? What would happen if your wishes come true?”
14. If you could change one thing about yourself, what would it be? Why this trait? Would these changes affect other areas of your
Deep conversation starters to get to know someone
Here is a list of deep conversation starters to get to know someone:
1. What do you think of the world today?
2. How would you change it?
3. What is your biggest fear?
4. Have you ever done something really brave in your life?
5. What made you decide to do it?
6. Do you believe in love at first sight? Why or why not?
7. Is there anything that you have dreamed of doing for a long time? Why haven’t you done it?
8. Do you think it’s possible to go through life without any regrets?
9. What has been the most embarrassing moment of your life so far?
10. If I could tell you your future, what would you want me to tell you?
11. What do you wish everyone would stop talking about already?
12. If I could give anyone a nickname, who would I give it to and what would I call them? Why did I choose that name for them?
13. Where do you see yourself five years from now and how are you planning to get there? What about ten years from now, how will your life be then?
14. What helps to pull you out of a bad mood when nothing else seems to work anymore?
Deep conversation starters about life
Here is a list of deep conversation starters about life:
1. What was the best decision you made in your life so far?
2. If you had to choose one person in history to bear witness to your life, who would it be? And what would they say about you?
3. What is one goal that you want to complete before you die?
4. What represents success for you?
5. What is the most important thing in life for you?
6. Would you rather be able to fly or breathe underwater? Why?
7. What is the bravest thing you’ve ever done in your life?
8. Have you ever been arrested? What happened?
9. Are you a morning person or night owl? Which do you prefer and why?
10. If money didn’t exist, what type of job would make your life fulfilling and why?
Deep conversation starters about the universe
The following are some really deep conversation starters about the universe:
1. If time and space are infinite, then is it possible that life could exist somewhere else in the universe? And if that’s the case, would we ever be able to contact other life forms?
2. What makes you totally unique?
3. What is your opinion on the influence of social media on human relationships?
4. Do you think it’s possible for a person to be good without God?
5. Would you rather be a highly respected, but poor person, or a very rich, but hated person?
6. What do you think is the most beautiful thing about the universe?
7. If someone wrote a book about your life, what would the title be and why?
8. What is your opinion about people that are too attached to their smartphones?
9. You are given the choice between living forever and being able to choose when you die. Which do you choose and why?
10. If you could live anywhere on this planet, where would it be and why?
11. What do you believe happens after we die?
12. What is your opinion about love at first sight and when did it happen to you (if ever)?
13. Who is the most important person in your life and why?
14. Do you believe that everyone deserves love or only special people deserve it? Why do you think so and
Deep conversation starters about the world
Here is a list of the best deep conversation starters about the world:
1. Are you happy with your life?
2. If you had one year to live, would you change the way you are living now? What would you do differently?
3. What’s something that most people don’t know about you?
4. What’s your biggest regret in life so far?
5. How do you think your friends would describe you in 3 words?
6. If you were given a choice to start over, what would you change in your life?
7. What’s the most important thing to remember in life?
8. What makes you smile? What makes you happy?
9. Would you rather be rich or happy? Why?
10. What is the relationship between happiness and money for you?
11. Do we need money to make us happy or are there more important things than money?
Deep dark conversation starters
Here is a list of deep dark conversation starters to ask anyone in any situation:
1. Why are you the way you are but not the other way?
2. Will you control yourself in times when you shouldn’t?
3. What’s one thing about yourself, personality-wise, that you wish you could change?
4. If you could go anywhere in the world where would you go and why?
5. If you were a superhero what superpower would you have and why?
6. What was one of the happiest moments of your life so far?
7. How do you feel about death? Do you think it will be painful or peaceful or possibly something else entirely?
8. Are there any events in history that changed the world for the better or worse and how so?
9. If someone wrote a biography on your life what would they title it and what would they say was your purpose on earth?
10. If someone asked to be your apprentice and learn all that you know, what would you teach them first as the most important lesson to learn about life or love?
11. If money wasn’t an option where would you live and who would be your roommates?
12. Do you think people are inherently evil?
Deep conversation starters questions
These are some amazing deep conversation starters questions:
1. What’s one thing you would like your partner to start doing?
2. What are the things that you can’t help but do?
3. Which social media platform do you like the most and why?
4. What’s a goal you want to achieve in the next 10 years?
5. What does your typical day look like?
6. What’s one thing you’re proud of in the past year?
7. What’s the best compliment you ever received?
8. What did you want to be when you were little?
9. If you could go back in time, what one thing would you change and why?
10. If they made a movie of your life, what actor/actress would play your part and why?
11. How do you feel about technology today?
12. Who is the person who has had the most influence on your life and how did they influence it?
13. Do you think it is better to grow up with or without siblings and why?
14. If money was not an issue, what would be your ideal job and why?