How to Have Deep Conversations (Step-by-Step)

“How can I have deep meaningful conversations with my friends? I feel like I always get stuck in small talk”

In this article, I’ll show how you can make conversation that feels more meaningful than the usual small talk. Here’s how to have deep conversations:

1. Start with small talk and gradually go deeper

You can’t just start a deep conversation out of the blue. You want to start the conversation with a few minutes of small talk. Small talk helps people warm up to more meaningful conversation.[1]

Make the transition from small talk natural asking gradually deeper questions or sharing gradually deeper thoughts.

For example, it can be natural to share a personal reflection after a few minutes of small talk, and talk about really deep matters first after meeting up with the person a few times.

2. Choose relaxed, intimate environments

Avoid deep conversations in loud or high-energy places or in groups. People usually go there to have fun and aren’t in the mood for deep, thoughtful talks. Deep conversations are best between only two people or friends who are in the right mood and already are comfortable with each other.

3. Bring up a deep subject you’re interested in

Bring up a deep conversation topic loosely related to whatever you’re talking about.

Talking about career: Yeah I think the end goal is finding something that feels meaningful. What’s meaningful to you?

Talking about the weather: I think the variation helps me really get that time is passing so I even like the shitty parts of the year. Is variation important to you in life?

Talking about social media: I’m wondering if social media has done the world a favor or disfavor. What do you think?

Talking computers and IT: “By the way, I read about this theory that we most likely live in a computer simulation”

Talking about spring: “Speaking of spring and how everything grows, I saw a documentary about how plants communicate with signals through their root system. It’s fascinating how we know so little about earth”. 

If you get a positive reaction, you’ll be able to delve deeper into the subject. If you don’t get a reaction, you can try mentioning something else later.

4. Find like-minded people

Sadly, many people don’t enjoy deep conversations. It helps to go to places where people share your interests: People who share your interests are also more likely to be like you in other ways.

Here’s our guide on how to find like-minded.

5. Ask a personal question about the subject

Ask something slightly personal about the subject to make the conversation personal. That makes it natural to ask even more personal questions later.

Examples of questions to ask if you’ve been stuck in small talk for a while

  • If you get stuck talking about how it’s hard to find an apartment nowadays, ask where they would live if money wasn’t an issue – and why.
  • If you get stuck talking about problems in society, ask if they dream about living somewhere else – and why.
  • If you talk about work, ask what they would do if they were to start their very own business – and why.
  • If you talk about how time flies, ask how they think they’ve changed over the years – and what made them change.

6. Share about yourself

Whenever you ask deep or personal questions, share about yourself, too. If not, they can feel interrogated.

However, don’t cut someone short in order to share. Sometimes it’s natural to let someone talk for a long time. Aim to share roughly as much during the course of the conversation.

If someone briefly mentions what they think of their job, you can later briefly mention what you think of your job.

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If someone tells a long, intimate story about their upbringing, you can later share a long, intimate story about your upbringing.

7. Ask follow-up questions

Ask several follow-up questions to go deeper into subjects. Shallow subjects can, after a few follow-up questions, become deep and meaningful.

In between your follow-up questions, you can share things about yourself so the person doesn’t feel interrogated.

Sometimes it takes several meetings to come this deep. Here’s a conversation I had with someone over the course of an entire night:

Me: How come you choose to be an engineer?

Him: There are many good job opportunities (Superficial answer)

Me, after sharing about myself as well: You said that you chose it because there are a lot of job opportunities, but there must be something inside of you that made you choose engineering specifically?

Him: Hmm yeah, good point! I think I’ve always liked building things. 

Me: Ah, I see. Why do you think you like that?

Him: Hmm.. I guess… it’s the feeling of creating something real.

Me, later: That’s interesting, what you said before about creating something real. [Shared my thoughts]. What is it you like, you think, about creating something real?”

Him: Maybe it has something to do with life and death, like, if you build something real, it might be there even when you’re not there. 

8. Show that you listen

It’s not enough to be a good listener, also show that you are present. When you do, people dare to open up more and your conversations become more meaningful.

  • If you realize that you’re thinking about what to say when the other person is done talking, move your attention back to what they’re actually saying.
  • Maintain eye contact all the time when someone’s talking (except for when they pause to formulate their thoughts)
  • Give feedback with “hmm”, “yeah”, and so on. (Be authentic with this – not over the top)
  • Be authentic in your facial expressions so that the other person sees that you react. (surprise, joy, contempt, confusion, etc)
  • Summarize what the other person says but with other words. They: I want to work somewhere where I can be social. You: A place where you can meet people. They: Exactly!

9. Go online

You can find like-minded on forums online that are up for deep and meaningful conversations. I prefer looking for like-minded around me like I described by the very beginning of this guide. But if you live in an area where there are no meetups, forums can help.

Reddit has subreddits for almost every thinkable form of interest. Check out AskPhilosophy. Also, you might be interested in our guide on how to make friends online.

10. Dare to share small vulnerabilities

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Say something that’s slightly vulnerable to make the other person comfortable with opening up, too.

If you talk about a corporate mingle, you can reveal “I can get really uncomfortable when I have to meet people”. This can encourage your friend to reveal something personal, as well.

This creates an environment where you’re okay with sharing more than the polished surface. It helps make ground for deeper and more meaningful conversations.

11. Gradually talk about more personal things

Talk about more and more personal things over the course of weeks and months.

If you talk about slightly personal things first, like “Do you rehearse in your head before you make a phone call?” you can gradually be more and more personal. After some time, you’ll be able to talk about very intimate, vulnerable experiences.

Research shows that gradually talking about more personal things is important to make close friends.[2] It’s also been shown that deeper, more substantive conversations are connected to increased happiness.[3]

12. Be delicate about controversial topics

Avoid controversial topics in small talk. But when you know someone, controversial topics can be very giving and interesting. It can help to talk from a third-person perspective so people don’t get defensive.

“I heard that some argue that electric scooters should be banned because there are many accidents, but others say that it’s the cities fault that doesn’t prioritize bike lanes.”

13. Talk about dreams

Dreams tell a lot about someone. Ask questions and mention things that move the conversation toward talking about dreams.

Talking about work: What’s your dream job?

Talking about how you’re tired of work: “What would you do if you had enough money to never work?”

Share your own dreams to balance up the conversation.

14. Ask open-ended questions

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Ask questions that inspire longer answers than just yes/no.

Close-ended question: Do you like your job?

Open-ended question: How do you feel about your job?

15. Be curious about underlying motivations

If someone tells you that they did something, you can ask about the underlying motivation. Be positive, so you don’t come off as questioning their choice.

Example 1 of going deeper:

They: I’m going for a vacation to Greece
You: Sounds nice! What inspired you to choose Greece?

Example 2 of going deeper:

They: I’m thinking about moving to some place smaller.
You: Oh, cool! What makes you want to leave the city?

Asking a question about their underlying motivation creates an opening for the other person to start talking about deeper things.

16. Share your feelings about the subject

Share how you feel rather than just talking about facts. Use that as a springboard into more personal conversation.

If someone talks about moving abroad, you could say “I get both excited and nervous when I imagine moving abroad. How do you feel about it?”

17. Mention things that interest you

Mention something you think is interesting if it feels like the other person might be interested in it.

They: How was your weekend?

You: Good: I watched a documentary about…. OR I finished a book about…. 

If the person asks more about it, you can delve into the subject.

18. Ask a deep question when there’s a moment of silence

There’s no need to complicate things, especially if you know the person already.

If someone’s already an acquaintance or a friend, you can ask about something more profound you have on your mind out of the blue.

(a moment of silence).

You: I have this thing that I’ve been thinking about…

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Viktor is a Counselor specialized in interpersonal communication and relationships. He manages Socialpro’s scientific review board. Follow on Twitter or read more.

Go to Comments (6)

6 thoughts on “How to Have Deep Conversations (Step-by-Step)”

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  1. hi there , your topic is so interesting . I deeply believe we are the same since I am an enlightened guy living in Iraq i do not find the right people to talk with . even my family see this as “weird” topics. can we get in touch bro ?

  2. Hey David, It sounds like you moved to a new city (NYC) a few years back? I had thought it was recent.

    Anyway, I actually majored in philosophy when I was in college. Not sure why I did. I suppose I didn’t know what I was doing at the time with my life, but found philosophy to be interesting.

    According to numerology, I’m a life path 16/7, which supposedly makes me philosophical as well as being a natural loner. I learned it’s NOT unusual to be totally alone in life when one has this life path, though it’s NOT recommended.

    Anyway, I imagine it’s hard to talk about philosophy unless one is in a group meant to talk about it or else you know someone well who has the same interest. Otherwise, one might come across like a dork.

    I just became interested in photography. I heard Shutterstock pays 25 cents for each time someone downloads a photo and so I decided to take my basic digital camera with me last week. I’ve never been interested in photography before, but now I think I’ll take it everywhere I go. It makes me more observant and this also takes my mind off myself. I might join a photography group.

    • Hey Jean, this was when I moved to Gothenburg some years ago, before NYC. I can see how that seemed confusing, I’ll rephrase it.

      Always appreciate your comments ? Joining a photography group sounds like a fantastic idea!


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