Deep Conversation Starters

Conversation Starters

When you only talk about your hobbies and the weather with a friend or someone you’ve met, it can get old. Why not try to connect with someone on a deeper level and talk about some interesting topics? If you’re talking to someone, this can be a way to learn more about them.

Deep conversation topics can help you talk about dreams and aspirations, goals for work and other things like that, as well as fears, accomplishments, challenges, and so on. You never know where your conversation will go because these topics are so important.

We’ve made a list of 500 conversation topics that are meant to help you build a stronger relationship with someone. The possibilities for what you can talk about and where the conversation can go are endless when you have deep conversations with people you don’t know very well. This is true whether you’re meeting someone new at work, in class, on a first date, looking for couples questions, or hanging out with old friends.

Make sure to check out the full list of 500 very interesting topics below.

Type 1 – Deep Conversation Starters

Which high school did you go to?

What are some things that you have been having to deal with on a daily basis in your life?

What is the thing that scares you the most?

When did you last cry?

What do you want to do next?

What was the best thing about being a child?

If you could, what would you change?

If you could have a superpower, what would you want to be able to do?

When it comes to real life, what is your super power?

Is it possible to live a good life?

Does everything happen for a reason? Why?

In what way is your family important to you?

Your strengths are:

In five years, where do you see yourself?

In the world, where would you like to go?

No, I don’t think so.

What do you think is the most important?

How do you spend your ideal day?

How do you think you’ll spend a million bucks?

As a child, you met your best friend.

Is there anything you want to do before you die?

A person who likes to get excited.

Money is important to you.

Do you enjoy going to the gym? What is your new plan?

In the town, or somewhere else?

No, I don’t. Do you own one?

What have you been watching a lot of lately?

No, I just let things happen as they happen.

No, I didn’t play any sports as a child.

Your life is going in what direction?

Rank these things in order of how important they are: family, work, and love life.

What has been the most difficult thing you’ve ever had to deal with in your whole life?

Where would you like to live? What’s the reason?

If money were not an issue, where would you go on vacation if you could go anywhere?

Is there someone in the book, movie, or TV show that you think is the most like you? Why?

When did you last do a lot of work?

When you’re bored, what do you do?

What two big changes in your life do you think are the most important?

Do you want to be a doctor? What is most important to you?

When you think back, what are some of the things you’d rather forget.

If so, what are they? Is that correct? If so, then which one?

What are two things you can tell me about two of your long-term friends? Why did you choose them?

What do you want to do at home? People break things. What would you do?

Would you rather do a simple job for someone else or one that was hard for you?

What were your favourite things about being a child?

Is there anything you would do if you won?

If you could go back to high school, what would you do?

If you could be any famous person, who would you be and why would you choose them?

Movies aren’t just for kids. If there were a movie in your life, what would happen at the end?

Is there anything you have done that has made you feel afraid?

Everything else in your life that you don’t want to have in it.

How did someone give you the best gift? What kind of feelings are there?

Type 2 – Deep Conversation Starters

  • Talk about a big event that made you become a better person.
  • What do you want to do in five years and ten?
  • Who is your favourite person, and why?
  • Someone did something nice or kind to you at some point. Tell us about a time when you did something nice for someone else.
  • If you won the lottery, what would you buy the first thing you would? Why?
  • Find things that are similar and different. Talk about them.
  • In what ways are you excited? The last exciting thing you did was:
  • What is your favourite piece of clothing and why?
  • In your life, what values are important to you and what do you value most? They were given to you by your parents, right? Then where did they come from?
  • What kind of date do you think is romantic? Make plans for a romantic date night together, and then you can do it.
  • What makes you most afraid? During childhood, what you were afraid of changed.
  • Discuss how you first thought of each other and whether it was correct.
  • It has changed a lot since you began dating. Give a few examples to back up your answer.
  • What would make you break up with someone? Would you be able to forgive and forget and start over with the person?
  • Have you ever had a bad dream? It was about what.
  • During what times and places do you feel most like your true self? Why?
  • Which celebrity are you most excited about seeing on the big screen? What do you like about them?
  • What traits do you think are important for a strong relationship? Do you have these qualities?
  • How do you feel about a social or political issue that you think is important? Why?
  • You were a child. What was your favourite book when you were young? Because it was your favourite.
  • My favourite movie as a child was… It still makes me happy. A lot of times.
  • Is there anything I should tell my adult self if I could go back in time?
  • A secret about yourself.
  • What would you do on a “dream day”? With someone else or alone?
  • Do you have a fear of anything? Why?
  • Is there anyone you’d like to be? Why?
  • Describe your biggest mistake.
  • A child, what did you want to be? The answer is yes.
  • What is your dream job? Do you think you will ever be able to get it?
  • How many siblings do you have, and are they older or younger than you are? How do you feel about them?
  • How did someone hurt or betray you? Tell us about it.
  • Tell us about the most difficult thing you’ve had to deal with so far in your life. No, I couldn’t. What did I learn?

Type 3 – Deep Conversation Starters

What do you enjoy the most?

After you wake up, what do you do first? Why?

What places are on your “bucket list”?

It’s time to think about your childhood habits. What are some that you still do?

What do you want in a friend?

Are you a good listener, or are you a good public speaker?

Who do you think is the best? Why?

In a person, what do you notice first?

Is there a song that fits you? No, I can’t.

You look up to who?

No, I don’t want to talk about embarrassing things.

If so, what is it?

The name of this year would be:

When it comes to expressing yourself, what’s one thing that you’ve been afraid to do?

When it’s too late, most people find out about it.

When you went to a new country, what was your most memorable “culture shock” moment?

During a dinner party, what do you think are the questions that should not be asked?

If you could, what would you change about yourself?

Is there anything you would do if you woke up one day and all of your problems were solved?

What scared you, but you did it anyway.

No, I don’t follow any strict rules.

To you, what makes a conversation important?

In ten years, what do you think will be a big no-no because it’s so popular now?

How important are the three things in your life?

How do you think of love?

How did you spend your last year?

Is there a bad habit you can think of?

How was school today?

How were you when I was your age?

How did you choose our names?

What are we going to do next summer?

The chances of you not meeting:

What’s the best meme you’ve seen in the last few days?

When you log in to your Facebook account, what email address do you use to do so?

To quit social media at the right time, you need to figure out when that is.

In the past, have you thought about meeting someone on social media.

There are a lot of things about social media that are interesting.

Newspapers might not be around in the future.

What’s the worst Zoom meeting you’ve ever had?

There is a lot of news right now.

Is there anything in the news that is having a big impact on your life?

Have you seen any funny videos from Facebook last night that you thought were funny?

News stories have an impact on your daily life.

As soon as you hear the word “Facebook,” what comes to your mind, and why?

If so, do you spend most of your time on social media sites?

What do you want for us?

What have you done for your family?

At school, did you get into trouble?

No, I didn’t play pranks on them.

Type 4 – Deep Conversation Starters

  • Would you rather be very well-known or very well-off?
  • In what situations, if any, is it OK to tell a big lie?
  • What are you thankful for?
  • How selfish are you?
  • What three words do you think people use to describe you the most?
  • People worry about a lot.
  • What do you wish more people knew about you?
  • What do you wish you were better at?
  • Name something that’s always worth it to spend money on.
  • The house of your dreams or a trip around the world?
  • Professionally, what drives you?
  • Is there anything you’ve done outside of work or school that you’ve put a lot of work into?
  • If you’re not a famous person, I want you to tell me who you admire the most.
  • How would you spend a million dollars if you could give it away?
  • Is it more important to forgive or to accept someone?
  • Do you think there is a higher power or something that isn’t in this world?
  • Have you ever given money to a person you didn’t know through a Kickstarter or a crowdfunding site? Tell me about the last one.

Type 5 – Deep Conversation Starters

Were you ever caught by police for breaking the law?

What was the job you didn’t like?

What are you good at?

During your younger years, what were you like?

I used to read you a lot of different books. What was your favourite?

How do you remember me when I was a child?

What do you think I want to be?

Because our grandfather had a crush on her.

You were close to which member of your family as a child.

The value of everyone’s life is the same, or is it not?

Were you ever caught lying?

Since when have you given up on a goal that you really want?

How have your strengths helped you to be more successful? In what ways have your flaws slowed you down?

Were you doing more harm than good when you were living on this Earth?

Describe how you learned to accept yourself and other people as they are.

How important is it for you to help yourself?

If so, why?

Why do people hold on to beliefs that can’t be proven?

In the virtual world, do we fall more in love with ourselves than we do in the real world?

If someone drowns and you don’t help them, are you responsible for their death?

Do you like to play outside?

What do you want me to say?

How do you spend a special day with each other, and what do you do?

Valentine’s Day is coming up. What do you want to get for him?

The first things we said to each other.

When you were in a relationship, what was the best advice you have ever been given?

Our time together is going well.

Type 6 – Deep Conversation Starters

  • If you could go anywhere in the world, where would you go? Tell us why you chose this.
  • What is your most important goal in life?
  • The next ten years, what do you think you’re going to be?
  • In the event that you got a tattoo, what would it be called? Why did you choose that?
  • Do you think that adults deserve to be treated with respect, or do you think that they should be treated They do, right?
  • You could change the world if you could. How would you do that?
  • To tell the truth or not? Do you think it will happen at all?
  • Which people do you like? Why?
  • A person should have these five things.
  • I’m grateful for three things.
  • What do you wish you could have done?
  • What has been the most risky thing you have ever done?
  • From your home, how far have you gone? How long did you stay there?
  • School is fun for me. Why not?
  • I like two things about myself.
  • In what situations do you get down?
  • How important is this person to you? There are a lot of ways to improve your relationship with this person.
  • Were there people in your life when you were young who had a big impact on you? Positive or negative: Was the effect good or bad?
  • If you died today, would there be anything you would have done or said that you would not have done?
  • It’s hard for you to do what it is that you don’t like.
  • Poetry, a storey, or a picture: Have you ever written or drawn one of these things? If so, then what?
  • Four things you want your friends to have.
  • How would you spend your last months? In what way?
  • What is the thing you value the most? Why?
  • In the event that you could have a superpower, which one would you choose to have and why?
  • Choose any time in history that would be best for you to live and see any event.
  • When you moved from each place, how old were you when you did? Which one did you like best?
  • What kind of person do you like and/or admire? Why?
  • As a theme song, what would you choose? Why?
  • After you die, what would you like people to say about you?
  • Is it possible for you to have any car you want? Which one would you choose?
  • Is there one thing you could do to help the world?
  • Were you able to help someone? Tell us about what you did.
  • What has been the best thing that has ever happened to you, and what is it?
  • It’s time to talk about something that made you laugh.
  • With anyone, where and with whom would you go on a trip if you could?
  • In your life, what has been the most difficult thing that you have had to deal with?
  • Is there anything you have ever done that scared you the most?
  • What are your biggest flaws? What are your best qualities?
  • Is there more than one child in your family? How old is each one of them? Are you near them?
  • I have had to deal with a personal tragedy in the past. How did the experience make you feel about yourself and what you thought about yourself?

Type 7 – Deep Conversation Starters

Are you still in touch with your ex?

No, I wouldn’t.

What is your favourite season?

How do you break up a relationship?

When do you feel the most alone?

We have a lot of different things that make us unique.

In life, what is always empty?

Is it possible for someone to be your best friend and your partner?

Is there anything I did as a child that you still don’t like?

As a friend, how do you feel about your family?

Who helped you with homework when you were a child?

Do your parents have any bad habits?

What have been the highs and lows of your life?


Forgive one person from your past. Who would it be? Why?


In one year, how would you spend your time?


Describe your ideal day.


Tell me about someone you used to be friends with but no longer are.

In the last few days, tell me about the kind thing you did for someone else.

What are you good at?

What’s your favourite thing to do alone?

What is the most important thing you’ve done in your life so far?

As a person, what do you think is the biggest mistake that you have ever made?

If you were out of your comfort zone, tell me about it.

In your life, what has been the most risky thing you’ve done? No, I wouldn’t.

One question about your future: What would you want to know?

When you travel, what makes you the most stressed out?

She yelled at me in public. How come?

How would you be able to tell that you’ve grown up?

Before I was born or after I was born, did you know what I was?

We need to study and learn about certain things in order to be ready to do our family’s job.

Is the way your family punishes you fair and equal?

No, I don’t think it’s right for kids to help with housework.

Do you think you could talk to your family about anything?

Type 8 – Deep Conversation Starters

  • Tell me about your love life.
  • In what way did you meet?
  • Because of the way you both look at things, your relationship is unique.
  • What would you do to your relationship if you had the chance?
  • When you think about your relationship, what do you think is the most important thing.
  • Which people in this world do you look up to when you want to have a good relationship?
  • When you think of a bad relationship, who is the person who comes to mind?
  • When you think of love, how do you think of it?
  • How do you know what to ask your partner in the morning?
  • What happened in your conversation partner’s childhood that made it hard?
  • What made your friend’s childhood great?
  • What are the parents of your partner like?
  • Do the parents of your partner love each other? They love each other in different ways.
  • If you want to be supportive, how do you know when to do so
  • When should you tell your partner the truth?
  • How do you know that you should tell your partner a white lie?
  • How do you know when your partner is happy?
  • How do you know if you’ve made your partner unhappy?
  • How do you know when your partner is angry?
  • What would you change about your relationship if you were in charge of making it?
  • What would you change about your past with your partner?
  • They belong to someone else.
  • How do you make sacrifices and decide together?
  • How do you find a middle ground?
  • Describe how you feel about each other.
  • Tell me about the last time you had a conversation with your partner that you found interesting.
  • The most important things you both talk about are:
  • They don’t talk about a lot of very important things.
  • When did you last play the 21-question game?
  • When was the last time you asked each other silly things?
  • When you and each other think of a good conversation, how do you think of it?
  • When you and your partner are having a bad conversation, how do you both describe it?
  • Both of you have different ideas about what understanding means to each of you.
  • A lot of people ask this question: “What do you think listening means?”
  • How long have you been married?