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400+ Deep Conversation Starters to Strike Gripping Conversations with Literally Anybody!

400+ Deep Conversation Starters to Strike Gripping Conversations with Literally Anybody!

Updated on Oct 13, 2022

Reviewed by Katina Tarver, MA (Mental Health and Wellness Counseling) , Life & Relationship Coach

400+ Deep Conversation Starters to Strike Gripping Conversations

If you’re here reading this, I am sure you are looking for a list of deep conversation starters, to strike a gripping conversation with your partner… your friends… or just anyone!

Don’t worry, we will not disappoint you!

These deep conversation topics are not just going to help you have a thought-provoking discussion, but they are also going to help you maintain the flow of enthusiasm in the usual chit-chat.

Well, let’s all admit one thing: to strike great conversations, asking fun questions is not all, the questions should be sensible enough to build interest during the span of discussion.

If you are looking forward to starting a conversation with someone and you don’t want to run out of deep questions in the middle of the conversation, this list is just for you!

But before you begin with the great conversation starters, let me first tell you…

400+ Deep Conversation Starters to Strike Gripping Conversations
400+ Deep Conversation Starters to Strike Gripping Conversations

How can deep conversation starters make an interesting conversation?

A deep conversation is generally mistaken for a boring conversation. That’s absolutely not the case. While scrolling down the questions, you will understand that deep topics can also make for a good conversation, here’s why.

Deep conversations are meant to be discussions on a substantial topic to talk about, that has a significant impact on our real life. Talking on such topics does not only make good utilization of time but it indeed leads to meaningful conversations.  

Most importantly, deep conversations are the best when you want to avoid a weak impression of a special person you are talking to. It is always better to sound intellectual and interesting rather than sounding creepy and foolish.

And, how do you call such topics boring when you can discuss some really interesting facts related to your love languages, goal in life, long-term relationships, biggest regret, previous relationships, love talking, and whatnot!

So, without any further ado, let us simply begin with our list of conversation starters for a magnetizing gossip.

To engage a person in your gossip, it is important that you are supplied with questions that suit a specific gender and age group. For Example, the list has a separate section for girls, guys, kids, adults, teens, and so on. Whether you want to talk to your boyfriend or a 10-year-old nephew, the list covers it all.

Let’s first begin with interesting questions to ask a girl.

Deep conversation starters with a girl

Girls are a little specific and sensitive about everything that goes around them. Hence, it is important that you play as safe as possible and stay away from the sensitive chords while picking some personal questions to ask a girl.

Don’t worry, as long as the list is there to guide you, nothing can stop you from grabbing some chit-chat. We’ll begin with small talks.

  1. Which high school did you graduate from?
  2. What are some day-to-day challenges that you have been facing in your life presently?
  3. What is your biggest deal-breaker?
  4. When was the last time you cried?
  5. What is the next big thing you want to accomplish?
  6. What was the best thing growing up?
  7. What one thing would you like to change if you got to?
  8. If you could have a superpower, what would it be?
  9. What is your real-life superpower?
  10. What do you think is the secret of a good life?
  11. Do you believe everything happens for a reason? Why?
  12. How important is your family to you?
  13. What are your strengths?
  14. Where do you see yourself in 5 years from now?
  15. If you could travel anywhere in the world, where would it be?
  16. Do you believe in karma?
  17. What do you value the most?
  18. What is your favorite memory from childhood?
  19. Do you believe in having a purpose behind every work?
  20. Why do you do what you do?

Those were some brilliant deep questions to ask a girl.

With girls being treated with such exclusivity, the boys must not be left out.

While girls are sensitive, boys are the easiest to get distracted from the topic of conversation if it fails to interest them. Agree? So, let’s have a deep conversation questions list for guys.

Deep conversation starters with a guy

The key to keeping a guy engaged in your conversation is to revolve around the topic that interests him in his day-to-day life.

It can be just about his best friend or his latest workout plan. Well, girls, believe it or not, not all guys are silent, let the boy speak and be a patient listener.

  1. How is your perfect day spent?
  2. How do you plan on spending a million dollars?
  3. How did you meet your best friend?
  4. What are the top three items on your bucket list?
  5. Are you an adrenaline junkie?
  6. How important is money to you?
  7. Do you like working out? What is your latest plan?
  8. Do you plan to settle in the town, or abroad?
  9. Do you like kids? Do you have one at home?
  10. What are you binge-watching lately?
  11. Do you have any plans for the future, or do you take things as they come?
  12. Were you into any kind of sport, growing up?
  13. Where do you see yourself, in the next 10 years?
  14. Do you like playing video games? Your favorites?
  15. What was your biggest dream, as a kid?
  16. Are you close to your family?
  17. Who was your biggest influence growing up?
  18. What are you grateful for, every day?
  19. What is the reason you think you were put on this planet?
  20. What part of your life would you like to simplify?

There you go.

If you know how to steer a conversation, not a single question must have dropped the interest down.

Next up, we have a list of the gems that are closest to our hearts. Who doesn’t like to hear them chatter all day about their schools, teachers, games, friends, and whatnot!

You must have guessed by now, coming up is Deep Conversation Starters for Kids.

Deep conversation starters for kids

Kids are not all about cuteness and innocence. The little hearts have so much more. However, to discover it, you must have a good set of questions to dig in.

Do you want to have a deeper insight into the child? Let’s go!

  1. Do you have any goals in life?
  2. Do you like chocolates?
  3. What are your favorite sports?
  4. What are your favorite video games?
  5. Whom do you like more, mom or dad?
  6. Do you like bedtime stories? What are your favorites?
  7. What is your favorite food?
  8. Do you believe in magic?
  9. Who is your favorite superhero?
  10. Do you read storybooks?
  11. Do you read comics?
  12. Do you believe in Aliens?
  13. What is your favorite season?
  14. What is your favorite cartoon?
  15. Do you like going to school?
  16. Who is your best friend?
  17. What is your favorite subject?
  18. What is your least favorite subject?
  19. Do you like staying up late, or waking up early?
  20. What is your favorite season?

You see, even late-night stories have such a deep influence on the youngsters.

Next up, we have another sensitive batch to deal with. The teenagers.

Teens hardly engage in conversations with someone who does not have a matching opinion or a similar viewpoint. Thus, you must be prepared with your list of topics if you’ve decided to speak with a teen.

Deep Conversation starters for teens

Traditional and conventional talk is the last thing that the teens appreciate.

Besides, you also need to stay alert that you don’t trigger negative emotions in the young spirits who are already going through massive hormonal imbalance and emotional extremes. Here you go with the list:

  1. What is the biggest goal of your life at present?
  2. How different is this generation?
  3. How often do you see other teens dating each other casually?
  4. What is special about the age that you’re in?
  5. Describe yourself in less than 5 words.
  6. What amendments would you make if you were president for a day?
  7. Where in the world would you preferably live?
  8. Would you be interested in watching a romantic movie or a horror movie?
  9. If you could eat dinner with 3 celebrities, who would they be?
  10. Are teenagers today grateful enough, or do they continue to crib?
  11. What do you do when you feel stressed?
  12. What do you feel is the hardest job in the world, and why?
  13. What advice would you give yourself, if you could travel anytime back in time?
  14. What is the worst thing that happened to you?
  15. How important do you think community service is?
  16. What are you most afraid of?
  17. What is your definition of complete happiness?
  18. What is your past, has a big impact on your present?
  19. Any bad habits you wish you could break?
  20. Are you a follower, or a leader?

Enjoying the conversation? Well, me too!

Now that we are done with the super-sensitive batches and specific types, it’s time for something enticing, grave, and consuming. The next list is about Deep conversation questions for adults.

Deep Conversation starters for Adults

Having a deep conversation is not difficult with adults, provided you have topics that they can actually consider deep.

With others being already mature and experienced, not every random topic is going to draw their deep attention. Let’s see what we have on the list for you.

  1. What are your favorite memories as a kid?
  2. What would you do if you won the lottery?
  3. What would you change if you could go back to high school?
  4. If you could be any celebrity, who would you be and why?
  5. If there were a movie in your life, what would be there in the climax?
  6. What is the scariest thing you have done?
  7. What would you like to eliminate from your life, completely?
  8. What is the best gift someone has ever given you? What emotions are attached to it?
  9. What is something you enjoy the most?
  10. What is the first thing you do, after waking up, every morning? Why?
  11. What destinations are there on your bucket list?
  12. What are some childhood habits you continue to do?
  13. What do you look for in a friend?
  14. Are you a good listener, or a good speaker?
  15. Whom do you admire the most? Why?
  16. What do you notice first in a person?
  17. What song describes you? Can you sing it?
  18. Whom do you look up to in life?
  19. Would you mind revealing embarrassing stories?
  20. Is there something you are really proud of?

Arresting and appealing, exactly the way we wanted it to be!

Coming next, are the list of deep conversation starters designed for a boyfriend.

Deep conversation starters with boyfriend

To indulge in deep gossip with your boyfriend is essential for a healthy relationship. Among all the fun, loving, and exciting adventures that unite both of you, it’s important to include some meaningful and serious discussions about life too.

This will just help you understand each other better for a good future. Here you go with some super amazing starters.

  1. How do you plan to spend the rest of your life?
  2. What are the first things you notice in someone of the opposite gender?
  3. What never fails to impress you?
  4. What are the most impressive qualities in a woman?
  5. What is a big turn-off for you?
  6. Have you ever been cheated on?
  7. Have you ever cheated on someone?
  8. How big a role does loyalty play when it comes to relationships for you?
  9. What are the things in a woman that annoy you?
  10. How can a woman turn you on?
  11. What’s the thing about relationships you learned, you wished you had learned earlier?
  12. What are the happiest memories of your past relationships?
  13. Anything you want to forget about your past?
  14. What was the lowest point in your life?
  15. What do you look for in a potential partner?
  16. Would you rather have multiple girlfriends or be a single woman man?
  17. Have you ever been on online dating apps?
  18. What makes you different from other people?
  19. What are your dream plans with your partner?
  20. Do you believe in monogamy?

Wasn’t it pure delight to know all the hidden viewpoints of the person you admire the most? Especially the relationship questions must have been worth diving in.

Next up, we have even great questions In The Deep Conversation Starters With Girlfriend list.

Deep conversation starters with girlfriend

Chocolates and alluring gifts might light up your girlfriend’s face with a genuine smile, but that’s not what a relationship is all about.

Your lady love would feel way more sought and important in your life if you gift her quality time with these wonderful set of deep conversation starters:

  1. Do you believe in opposites attract?
  2. What never fails to turn you off in a man?
  3. What is a big red flag?
  4. What is a big turn-on?
  5. What would a normal day, in your perfect life, look like?
  6. What do you think a man’s role is, in a relationship?
  7. What do you think is the role of a woman in a relationship?
  8. Do you believe in open relationships?
  9. What was the most serious relationship you have had?
  10. What are the three most annoying things your boyfriend can do, and you will hate him for all that?
  11. Any adventurous stories with your partner?
  12. Are you an indoor, or outdoor person?
  13. What are a few things you value the most?
  14. What do you do, when someone is mean to you?
  15. What are your favorite movies or TV Shows?
  16. How are your ideal weekends spent?
  17. How good are you when it comes to managing finances?
  18. What do you need to vent about?
  19. What songs are there in your playlist?
  20. What are a few must-haves, in your potential partner?

That must have felt great to talk your heart out on those small and delicate matters that really count in the bigger picture of our life.

Since the girlfriends and boyfriends have already been provided with their quality time with the special conversation starters, it’s time for your friends. You absolutely didn’t think of leaving them alone!

The coming list is deep conversation starters for friends:

Deep conversation starters for friends

If you are sitting idle feeling gloomy, and you want to convert the redundancy into a quality investment of time, reach out to your cell phone, take a few friends on a conference, and have a deep digging conversation!

Or else, if all of you reside nearby, head to your favorite cafe, take your seats around a table because this conversation is going to fade away all the murkiness with absorbing gossip…

  1. What is something about yourself you never wish to change?
  2. What novels or books have had a big influence on you?
  3. What strange habits do you have?
  4. What is your best quality to be friends?
  5. What are the fears, you wish to overcome?
  6. What person do you want to be like?
  7. What was your favorite fairy tale, growing up?
  8. What are your greatest accomplishments?
  9. Do you believe in helping strangers?
  10. What is your earliest childhood memory?
  11. If there was a time machine, would you go ahead, or behind time?
  12. How is your most pleasant hour spent?
  13. Where in the world would you like to have dinner, if it could be anywhere?
  14. Do you have any philosophical questions in your mind right now?
  15. What makes you shiver: water or height?
  16. What is your opinion on inter-caste marriages?
  17. Do you face imposter syndrome?
  18. When do you feel most lonely?
  19. Do you have double faces for the world?
  20. Are there any lessons you learned in the past year?

Couldn’t have been a better use of your time, the list, and the friends!

But we have another option for you.

In case you don’t want to be surrounded by all your friends and you just need your bestie to have a thorough discussion on life, the next list of questions is for you!

Deep conversation starters for best friends

You might not have a dozen friends but even one genuine friend is enough to have a deep discussion on any issue that concerns your life.

Having a heartfelt conversation with your best friend brings you closer to each other, develops trust and bonding, thereby making both of you feel equally content and gratified with the discussion.

So go on and relish the heart-to-heart discussion with your bestie:

  1. What has been your fondest summer vacation memory?
  2. Did you have any negative or traumatic experiences as a child?
  3. Did you ever commit a mistake, you wished you handled differently?
  4. Did you have a close non-blood relationship growing up?
  5. Who was the last person who broke your heart?
  6. Do you have any embarrassing childhood stories?
  7. Have you ever been arrested?
  8. Are you into anime?
  9. Do you have any embarrassing drunk stories?
  10. What year made you the happiest?
  11. Who was your first celebrity crush?
  12. Do you believe in either ghosts or aliens?
  13. If going back in time was an option, which historical person would you like to talk to?
  14. If you had a career in sports, which sport would it be?
  15. Is there a movie dialogue or quote, you live by?
  16. What do you think happens to oneself, after he or she dies?
  17. Where do you see yourself in the next 20 years?
  18. Do you believe in destiny and Karma?
  19. What are the things you hate to regret?
  20. What never fails to inspire you?

Before we move on to the next list, you must be grateful that you have someone to accept your vulnerable self. A deep bonding has no place for judgments and fake show-offs. Best friends are the best to reach out to when you are in need of advice and suggestions.

However, there is another place where you can have some serious discussions whenever you are stuck in need of some suggestions, your family. That takes you to the list of deep conversation starters for the family.

Deep conversation starters for family

Even if you live with your family, it is not necessary that you are well aware of their deep ideas and opinions.

None of us would want to miss the opportunity to have all the members of the family sitting around to make a great conversation. So go on and have a grooving chitter-chatter with your family:

  1. How did you spend the entire day?
  2. What was the longest time for which you stayed away from the house?
  3. How was school today?
  4. How were you, when you were my age?
  5. How did you come up with our names?
  6. What are we planning for our next summer vacation?
  7. What were the odds of you guys not meeting?
  8. What are your dreams for us?
  9. What are the things you have sacrificed for your family?
  10. As a teenager, did you get into trouble?
  11. Did you ever play pranks on your cousins?
  12. Did you ever get arrested for breaking the law?
  13. What was the job you hated?
  14. What are your hidden talents?
  15. What are the silly things you used to do?
  16. What was your favorite book, you used to read me?
  17. What are your first memories of me?
  18. What do you think I dream of becoming?
  19. How did our grandfather meet our grandmother?
  20. Which family member were you closest to, growing up?

While we see most of the families splitting into nuclear families, finding time with family becomes a dream.

Now that you have had such lovely and constructive gossip with the family members, do we have some love birds looking for deep questions for couples? Your wish is granted!

Next up, we have deep conversation starters for couples.

Deep conversation starters for couples

Snuggling and cuddling is not enough, couples need to have some constructive conversations to keep them connected as soulmates.

And when doing so can bring in some interesting answers, there is no reason to skip the list. Here you go with the questions.

  1. Where are most of your date nights spent?
  2. How do you guys connect on a deeper level?
  3. What brings you closer as soulmates?
  4. Where do you want to go for your next vacation?
  5. Are you a mountain or beach person?
  6. Do you want things to change?
  7. What are your plans for the future?
  8. What are your thoughts on marriage?
  9. What is one annoying habit of mine you want to change?
  10. What is it that you love the most about our relationship?
  11. How do you think things will change in the future?
  12. Which city or country do you want to settle down in?
  13. What do you want our first house to be like?
  14. Did you have a toxic ex in the past?
  15. Is there anything you are struggling with, and want us to get through it together?
  16. How has life changed after we started dating?
  17. Is there any time when you think about your ex?
  18. Are you comfortable with my parents?
  19. Can we discuss our first love stories?
  20. What makes you so perfect and adorable for me?

That’s what we call, a soulful chat. Moving on, we have a bonus deep conversation starters list for married couples.

Marriage not only brings two people together in a house, but it also adds some huge responsibilities that hardly allow the couple to have a gratifying conversation. Don’t worry this time, you made it!

Deep conversation starters for married couples

The Spark in marriage is not just about romance, it’s also about togetherness, a deep understanding of each other’s emotions, and supporting each other in the struggling phases of life. 

You must have a lot to speak on such grave topics, let’s see what we have on the list for you.

  1. What’s your love story?
  2. Was it love at first sight with me?
  3. Do you have any suggestions for romantic getaways?
  4. Was it a long time you guys dated, before getting married?
  5. When did you know I was the one?
  6. Was it an arranged marriage or a love marriage?
  7. Do you want kids in the future? How many?
  8. How do you keep the relationship spark alive?
  9. If not in this city, where in the world would you want to live?
  10. What movies never fail to make you cry?
  11. How do you make finances work as a couple?
  12. How normal are arguments between us?
  13. How do you figure out how to balance the daily chores?
  14. What were your first impressions of your partner?
  15. When did things actually get serious?
  16. What was the most special part of your wedding?
  17. Where did you celebrate your first wedding anniversary?
  18. How often do you make time for each other?
  19. How have things changed from the time we dated?
  20. What, as a couple, makes you feel most peaceful?

Enjoyed hopping down the list? If yes, great! Coming next is something special. Remember the phone call conversations that go blank after a few minutes?

You really want to talk to the person for a little longer but you just don’t have a sensible topic to continue. This won’t happen anymore.

The next topic won’t let you run out of questions when you’re on a call. After all, it’s a list of deep conversation starters for phones.

Deep conversation starters for Phone

After a “Hello”, and “How are you?”; the only question we are left with is “what’s new?”, or “Give Some Gossip”.

It’s perfectly fine to have gossip, but why not take the gossip to a more personal and intense one!

If you don’t know how to make it happen, the list is of course here to guide you.

  1. Why don’t you tell me something about yourself?
  2. What don’t you tell me about your background?
  3. What makes you choose this, as a profession?
  4. When did you apply for your present job?
  5. What made you leave your last job?
  6. What makes you want this so bad?
  7. What do you know about this position?
  8. What is your dream company?
  9. Why do you want to work there?
  10. What are you most passionate about?
  11. What are your expectations of us?
  12. How many other companies are you interviewing with?
  13. When did you last talk to me in person?
  14. Is there anything you want to vent about?
  15. Tell me a rumor about yourself that is true?
  16. What kind of leadership style do you prefer?
  17. Anything you want to ask?
  18. How are you doing emotionally?
  19. What traits do you excel at?
  20. What are your weaknesses?

While most of us feel lazy to text, a major reason for being so reluctant to converse on text messages is not having an interesting topic that can drive the discussion.

If you are fond of having text chats more often, you must go through the next list which is Deep conversation starters for texting.

Deep conversation starters for texting

Text chats often end with exchanging some funny jokes and compliments for profile pictures. If you have just met a special friend and you’re uncomfortable calling up, texts must be your best friend! 

You must be looking for some topics to discuss, that can help you know more about your new-found friend. So, here you go!

  1. What is your go-to GIF for a laugh? Why?
  2. What song do you play most often?
  3. What is your go-to quote, when you are feeling low?
  4. Is there any joke you remember by heart?
  5. What’s the weirdest text you have received?
  6. What are your favorite memes?
  7. What is the most interesting thing near you?
  8. What are your most recommended applications?
  9. What is the worst text you have accidentally sent?
  10. What are things you really want to buy?
  11. What is the funniest picture you have of yourself?
  12. What are the dumbest pick-up lines, you know?
  13. What’s your most useless talent?
  14. What celebrity do you absolutely love?
  15. What body part you won’t mind losing?
  16. What is the dumbest way you injured yourself?
  17. How often have you actually bunked school?
  18. What is the most interesting thing you have read this week?
  19. What is the most ridiculous thing someone tricked you into doing?
  20. When was the last time you spoke with someone for so long, on text?  

You see how grooving text conversations can be, especially if you want to have the best impression on a special person you just met.

This reminds of the ones who have just entered into relationships. And thus, the next list is dedicated to them because it’s deep conversation starters relationships.

Deep conversation starters relationships

There is a phase where you have just entered into a relationship but you have neither laddered up to a girlfriend-boyfriend status nor a couple.

It is natural to be clueless about the topics of discussion when both of you want to present your best self forward.

And the only type of conversation you must have right now is a deep conversation. Go on the list is all yours.

  1. What are some annoying habits of other couples you hate?
  2. What kind of a parent, you think you will be?
  3. If you are having a bad day, what do you want me to do?
  4. What do you think, do I understand your feelings?
  5. How content are you with this relationship?
  6. What are your favorite activities to do outdoors?
  7. What do you want me to answer truthfully?
  8. How do you spend a special day with each other?
  9. What do you want for Valentine?
  10. Do you remember the first things we said to each other?
  11. What is the best relationship advice ever given to you?
  12. Are you happy with the amount of time we are spending together?
  13. Are you still friends with your ex?
  14. Would you ever lie to someone, to make them happy?
  15. What is your most favorite part of the year?
  16. What is a big relationship deal-breaker?
  17. What are the times when you feel most lonely?
  18. What are the biggest differences between us?
  19. What is something in life, which always feels empty?
  20. Do you think someone can be your best friend and your partner?

Fair enough! Friends, families, couples, guys, girls, girlfriends, boyfriends, teens, adults, kids, and a few more. We have come a long way.

After you’ve been through the list compiled for each of the age groups and relationships, it’s time to take a look into a few other lists of deep conversation starters that do not target a specific age group or a relationship but are as engaging as it can get.

Deep conversation starters about life

We all have a personal opinion and a unique perception about life which we hardly discuss until and unless you are sitting with the right person.

If you have found the right person to have such a discussion with, this list is all about it.

  1. Do you think dreams are a reflection of someone’s deep inner self?
  2. Do you sometimes feel really old?
  3. How often do you zone out?
  4. What are some things about your religion which always make you proud?
  5. What does happiness mean to you?
  6. What do you love about your nation?
  7. If I ask you to name all the things you love, how long will it take for you to name yourself?
  8. What little things give you joy?
  9. How many times have you been to a Palm reader?
  10. How often do you end up showing your anger and sadness?
  11. What do you do, when you feel lost?
  12. How do you celebrate your success?
  13. How well do you sleep when you’re stressed out?
  14. What is your passion, you want to decide on a career for your children?
  15. Do you do what you love the most?
  16. How far do you think you are, from achieving your goals?
  17. What is the deepest regret in this life?
  18. What for you, is success?
  19. What for you, is love?
  20. Do you believe in setting realistic ambitions?
  21. What experiences have helped you evolve into a better human being?

For some success matters more than money and for some money is a success, life is a different Puzzle for all of us. That was too much grilling and shoving though!

For the next list, let it be a little easier and lighter without compromising on the depth of the topics. It’s Deep dinner party conversation starters:

Deep Dinner Party Conversation starters

Dinner parties often end up in fun gatherings, but who said we cannot have fun with a deep conversation at the dinner party! Don’t you believe it?

Well, you need to scroll down the list and check it for yourself:

  1. How are things going at your workplace at present?
  2. What kind of work have you been doing recently?
  3. How are your days going recently?
  4. What were you up to last night? Did it turn out to be as expected?
  5. How did you two end up meeting?
  6. Are you a cat person or a dog person?
  7. What was the worst astonishment you ever received?
  8. What makes you the happiest in life?
  9. How many siblings do you have?
  10. Where do you like to vacation, mountains, or beaches?
  11. What is your favorite pizza topping?
  12. Where have you made investments lately?
  13. What is the first thing you would buy, if you end up winning a mega lottery?
  14. How would you describe your family?
  15. What was the latest movie or TV Show you watched?
  16. If you had a chance to change your name, what would it be?
  17. What is the best gift you received; you cherished the most?
  18. If you had to open a restaurant, what would you name the signature dish?
  19. What is the goal you plan to achieve this year?
  20. Are you early birdy, or a night owl?

Do you still think the conversation cannot be fun? No way!

If you wish to take the fun on a “deeper” level, the next list is waiting for you,

Good deep conversation starters

If you are wondering what good deep conversation starters can bring, the answer is simple. This list has endless goodness for you to dig in.

Starting from spirituality to humanity, the list begins and ends with goodness. Interesting, right? What are you waiting for, go on and hit the list!

  1. Are you a spiritual person?
  2. What does spirituality mean to you?
  3. What are the toughest times you have been there?
  4. If you find out you are going to die tomorrow, what will you do today?
  5. According to you, can money buy happiness?
  6. If you could go back and change something, what would it be, and why?
  7. How will your closest friends describe you?
  8. If you could only keep five things with yourself, what would the five be?
  9. After dying, how would you want to be remembered?
  10. What does freedom mean to you?
  11. What about you, makes everyone smile?
  12. What is something big you are planning for the coming years?
  13. What is a lesson your parents taught you?
  14. What comes to your mind when I say success?
  15. What, according to you, are the best and worst things about growing up?
  16. Are there people in your life you would take a bullet for?
  17. If you could do something for your country, what would it be?
  18. Would you rather be hated, or forgotten?
  19. What is one thing, without whom, society will be a better place?
  20. How important are humanity and humanitarian services for you?

Told you, this was all about goodness! While deep conversations are amusing and good, deep conversations are intellectual too.

What can be better than having an intellectual impression while making a conversation to a senior colleague?

Don’t worry, you don’t have to work hard for it. You already have a list to guide you right below!

Deep intellectual conversation starters

If you have met a person for whom conversations on random and trivial matters are a big NO, you might want to remain quiet. But does that make sense?

Not all wise men are meant to be quiet!

An intellectual deep conversation can save you both from the unappreciated judgment and even awkward silence. Here you go with the only list you would need.  

  1. What is politics to you?
  2. Would you ever consider being a politician?
  3. What is one thing you would want to accomplish, by the end of your life?
  4. How do you make friends?
  5. What is one thing you cherish the most about your family?
  6. What is your biggest fear in love?
  7. What do you think society could improve upon?
  8. What is a hard thing you have to do at work?
  9. What makes you stand out in a crowd?
  10. When was the last time you felt lonely?
  11. What makes a conversation meaningful to you?
  12. How did you reach where you’re today?
  13. How do you define romantic relationships?
  14. Who has had a big impact on your life?
  15. According to you, are we all equal or not?
  16. Do human beings gravitate towards money, love or success?
  17. What unsettles you the most in the world?
  18. Do you believe in astrology?
  19. What was the most important event that shaped your life?
  20. Does life have a meaning, according to you?

That was pretty clean, deep, and effortless! It must have been a good escape from all sorts of risk in an intellectual discussion.

Now it’s time for the last list of deep conversation starters and we want to have the best of it. One last list for another interlocking deep discussion, and this time it will be the best.

Best deep conversation starters

The list of best deep conversation starters includes the best questions out there to lock an engulfing conversation. 

Whether it is about some deep sacrifices or the drowning emotions of anxiety, chatter it all away with this list!

  1. Do you want to leave a legacy behind?
  2. Would you prefer to die sacrificing your life for someone?
  3. If getting back to your childhood was an option, would you?
  4. What is the best way of dealing with stress and anxiety?
  5. How often do you end up embarrassing yourself?
  6. What is the scariest thing you have done?
  7. Are you big on small talk, or prefer deep conversations?
  8. What habits of humans annoy you the most?
  9. What brings out the best in you?
  10. How does one become successful, is it because of character, circumstances, or sheer hard work?
  11. How much do you read?
  12. What are your biggest faults?
  13. Is the pursuit of happiness the most important thing?
  14. If the world was ending in a week, what would you be doing?
  15. Can right exist without wrong, like good without evil?
  16. Who is your most admirable friend?
  17. Do you work to live, or live to work?
  18. Have you ever worked on your personality, or is it what you were born with?
  19. Who among your friends knows you the best?
  20. Do you believe in the afterlife or concepts of rebirth?

With this being the last list of deep conversation starters, there can never be an end to the deep discussion until you want to give up on drilling the topics further!

By the way, did you feel hesitant or nervous at any point on the list?

I’m sure most of you said yes. So, here are 5 tips on how to have a deep conversation. Once you are through the tips, you will be able to have a deep conversation with doubled confidence.

5 Tips on how to have a deep conversation topics

The key to having a deep conversation is to have the right person in front of you. I’m sure you agree with me.

But other than that, here are a few other prime tips that can help you have an interesting deep conversation without getting distracted in the middle of the interaction.

If you don’t want to miss such super-effective tips, go on and explore them thoroughly!

1. Start with small talk first

…and gradually dig in!

When having a detailed discussion on a topic, starting abruptly with an intense topic becomes misleading. A good question won’t necessarily make your conversation deep and captivating instantly, it is a process that should take a small start and gradually pick up the depth.

Imagine you are visiting a friend and the friend out of the blue poses a spontaneous serious question such as: “what lessons have you been taught by your parents?” Disgusting! That’s exactly the point; you would feel disgusted.

Thus, never begin a deep conversation with a sudden deep, and great question.  Start with simple questions such as: “What are your favorite memories with (xyz…)?” After this, you can eventually take it to a deeper level.

2. Be mindful of the environment

Having a deep conversation is great, especially with such mind-blowing deep conversation starters. But never ever forget to check the surroundings before you attempt to start a conversation.

Are the people around you in a favorable mood to have a deep conversation or they would rather talk about life? Make sure the environment is fit for having serious interactions and a deep discussion that does not derail into a debate.

3. Share “deep” things about yourself too

Firing deep questions one after the other won’t suffice. A conversation has to have equal reciprocation from both sides. If you are having a deep conversation, it should have an equal level of depth in your expressions too.

Besides listening to others’ facts and stories, you must let your experiences and thoughts surface the talk. Don’t step back from sharing the deep feelings, emotions, and opinions that hover in your mind.

It can be a simple affirmation following someone else’s answer such as: “Yes, even I don’t trust palm readers!”

4. Be present in the conversation

Asking questions and sharing your opinions won’t do it all either. A good interaction demands the involvement of all the people.

Besides being a good speaker, you have to be a good listener and stay attentive to what others are speaking.

You need to be present in the conversation. Showing your presence is only possible when you are actually present in the discussion. However, there are few actions to prove your presence.

Maintaining eye contact with the people, affirming or questioning their ideas, posing follow-up questions, and praising their thoughts are a few genuine ways.

5. Don’t be afraid to share your vulnerabilities

Once, I heard a celebrity saying, “for me intimacy is being able to tolerate someone’s vulnerabilities and having the same person to tolerate my vulnerabilities”!

Did it sound like one of the perfect definitions for intimacy? For me, it did! Your friends, family, and loved ones have the complete right to know the vulnerable side of yours.

In fact, they must stand by you in your tough times and be a constant pillar of support to you. The same is expected from you towards them.

Needless to say, having a deep conversation is incomplete without sharing such vulnerable experiences and letting go of all those bottled up and pent-up feelings of vulnerability.

That’s it! That was indeed a lot of information and suggestions to have an arresting deep conversation.

Over to you…

You can never have enough drilling and digging into the deep topics!

It must have been a delightful experience to share such intense threads of stories and beliefs of your life. And that brings us to the end of our deep conversation list too.

Well, just in case you want to have more of it, no one ever forced you to stop either! Haven’t you already been served with the tips on having a deep conversation? That’s all you need!

Scroll up once again, hunt for a deep topic and try framing a deep question yourself!