How To Have Deep Conversations (With Examples)

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

In this article, I’ll show you how to start deep conversations that feel more meaningful than small talk and keep them going.

1. Start with small talk and gradually go deeper

You may have seen lists of “deep conversation starters” online, but if you begin a deep conversation out of the blue, you’ll come across as too intense. Instead, start the conversation with a few minutes of small talk. Small talk is like a social warmup that gets people ready for more in-depth discussions.[1]

Make the transition from small talk feel natural by gradually making your questions and remarks deeper. For example, most people find it natural to share a personal reflection after a few minutes of small talk and to talk about more intense subjects after several meetups.

2. Choose relaxed, intimate environments

Avoid trying to have deep conversations in loud environments, high-energy places, or when you are socializing in a group. In these situations, people are usually focusing on having fun. They are unlikely to be in the mood for thoughtful exchanges.

Deep conversations work best between two people or a small group of friends who already feel comfortable with each other. Everyone needs to be in the right mood for a meaningful conversation, or else it will dry up quickly.

3. Bring up a deep subject that interests you

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

For example:

When talking about careers: Yeah, I think the end goal is finding something that feels meaningful. What’s meaningful to you?

When talking about the weather: I think when the weather is so varied, it really helps me remember that time is passing, so I even like the shitty parts of the year. Is variation important to you in life?

When talking about social media: I’m wondering if social media has done the world a favor or just created new problems. What do you think?

When talking about computers and IT: By the way, I read about this theory that we most likely live in a computer simulation. Have you ever thought about that?

When 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 the earth.

If you get a positive reaction, you’ll be able to delve deeper into the subject. If not, try again later. It may take a few tries before you find a subject you both like.

4. Find like-minded people

Sadly, many people don’t enjoy deep talks. Some are happy to stick to small talk, and others simply don’t know how to have deeper conversations.

It can help to look for people who share your hobbies or interests. Try to find a local meetup or class that meets on a regular basis. There’s a good chance you’ll find people that would like to talk about things you find fascinating.

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

5. Ask a personal question about the subject

Ask something slightly personal about the subject to take the conversation to a deeper level. That makes it natural to ask even more personal questions later on.

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 fast time flies, ask how they think they’ve changed over the years – and what made them change.

6. Share something about yourself

Whenever you ask deep or personal questions, share something about yourself too. If you ask a series of questions without revealing anything personal in return, the other person may feel as though you are interrogating them.

However, don’t cut someone off just because you think it’s time to contribute to the conversation. Sometimes it’s OK to let someone talk for a long time.

Try to keep the conversation balanced so that you are both sharing roughly the same amount of information. For example, if someone briefly mentions what they think of their job, you can tell them briefly what you think of yours.

At the same time, you want to avoid oversharing. Sharing too much private information with someone can make them uncomfortable and can make the conversation awkward. If you aren’t sure whether you’re oversharing, ask yourself, “Is this relevant to the conversation, and is it creating a connection between us?”

See this guide on how to stop oversharing for more advice.

7. Ask follow-up questions

Follow-up questions can move trivial or dull topics in a deeper and more meaningful direction. In between your follow-up questions, you can share things about yourself.

Sometimes it takes several exchanges before you and the other person feel comfortable enough to share your thoughts and opinions.

For example, here’s a talk I had with someone over the course of an entire night:

Me: How did you choose to become an engineer?

Him: There are many good job opportunities. [Superficial answer]

Me, after sharing about myself: 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 that is?

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. [Sharing my thoughts] What is it that you like about creating something real?”

Him: Maybe it has something to do with life and death, like, if you build something real, it might still be there even when you’re gone.

8. Show that you are listening

It’s not enough to be a good listener. You also need to show that you are present in the conversation. When people sense that you are truly paying attention, they dare to open up. As a result, 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 in the present moment.
  • 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 – don’t go over the top.)
  • Be authentic in your facial expressions. Let the other person see how you feel.
  • Summarize what the other person is saying using your own words. This shows that you have understood them. For example: They: I want to work somewhere where I can be social. You: You want to work in a place where you can meet people. They: Exactly!

9. Go online

Online forums are a great place to find like-minded people who are up for deep and meaningful conversations.

I prefer looking for like-minded people who live near me. But if you live in an area where there are no in-person meetups, forums can help.

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

10. Dare to share small vulnerabilities

Show that you are a relatable, vulnerable human being by sharing a small insecurity. This can make the other person comfortable with opening up in return.

For example, if you talk about going to corporate mingles, you could say, “I can get really uncomfortable when I have to meet new people.”

When you share your vulnerabilities, you create a safe space where you and the other person can go beyond superficial interactions and get to know each other on a deeper level. This environment lays the ground for personal, meaningful conversations.

11. Gradually talk about more personal things

As you talk to someone over weeks and months, you can discuss increasingly personal topics.

For example, when you haven’t known someone very long, you can ask slightly personal questions like, “Do you ever rehearse what you’re going to say in your head before you make a phone call?”

As you become closer, you can gradually switch to more personal subjects. After some time, you’ll be able to talk about very intimate, vulnerable experiences.

Psychologists have found that talking about increasingly personal things brings people closer together and that mutual self-disclosure is key if you want to develop a close friendship.[2] Research also shows that having deeper, more substantive conversations with other people is linked to higher levels of happiness.[3]

12. Handle controversial topics delicately

You should avoid controversial topics in small talk, such as politics, religion, and sex. But if you already know each other, talking about controversial issues can be very enjoyable.

If you present an opinion from a third-person perspective, it can stop your listener from becoming defensive.

Example:

I’ve heard some people argue that electric scooters should be banned because they cause a lot of accidents, but others say that it’s the city officials’ fault because they don’t prioritize bike lanes. What do you think?

Be prepared to change the subject if the other person looks uneasy. Watch their body language. If they fold their arms, frown, or turn so that they are angled away from you, talk about something else.

13. Talk about dreams

A person’s dreams reveal a lot about them. Ask questions and mention things that move the conversation towards the things they’d love to do.

Examples:

When you’re talking about work: What’s your dream job? or, What would you do if you had so much money that you never had to work?

When you’re talking about travel: Where would you most like to go if you had an unlimited budget?

Share your own dreams to keep the conversation balanced.

14. Ask open-ended questions

Ask questions that inspire longer answers than just “Yes” or “No.”

Close-ended question: Do you like your job?

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

Open questions usually start with “How,” “Why,” “Who,” or “What.”

15. Be curious about underlying motivations

If someone tells you about something they’ve done or want to do, you can ask a question that reveals their underlying motivation. Be positive. You don’t want the other person to think that you are criticizing their decisions.

Example:

They: I’m going to Greece for a vacation.

You: Sounds nice! What inspired you to choose Greece?

Example:

They: I’m thinking about moving to a small town.

You: Oh, cool! What makes you want to leave the city?

They: Well, living in a town is cheaper, and I want to save up money so I can go traveling.

You: That’s awesome! Where would you most love to go?

They: I’ve always dreamed of going to…

16. Share your feelings about a subject

Go beyond facts and share how you feel. This can be a good springboard to a deeper conversation.

For example, 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

When you get the chance, mention things you’ve recently done or seen that you’d like to talk about. If the other person asks follow-up questions, you can delve deeper into the topic.

Example:

They: How was your weekend?

You: Good! I watched a great documentary about robots. There was a segment on how our generation will probably all have robot carers when we’re older.

They: Really? Like, caring robots will be a common thing for normal people?

You: Sure. There was a guy on there talking about how they’ll be like friends too, not just helpers.

They: That’s so cool…I think. But also, I’ve often thought that when I get old, I’ll want to spend more time talking to people because… [continues sharing personal thoughts]

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

Launching into a deep conversation with someone you barely know can make you come across as socially unskilled. But if someone’s already an acquaintance or a friend, you can ask a profound question out of the blue if there’s something on your mind.

Example:

[After a moment of silence]

You: Recently I’ve been thinking a lot about…

19. Ask for advice

If you ask someone for advice, you’ll give them an easy way to talk about their own experiences. This can lead to some deep and personal conversations.

For example:

They: I retrained as a nurse after working as an engineer for ten years. It was a huge change!

You: Cool! Actually, maybe I could use your advice. Can I ask you something about switching careers?

They: Sure, what’s up?

You: I’m thinking about retraining as a therapist, but I feel very self-conscious about going back to school in my 30’s. Was that something you had to deal with?

They: At first, yes. I mean, when I studied engineering, obviously I was a lot younger, and my attitude to schooling was… [continues sharing their story]

Only ask for advice if you really want and need it. Otherwise, you may come across as insincere.

20. Don’t push your views onto other people

If you try to convert someone to your way of thinking, they will probably shut down, especially if they hold a very different opinion.

Instead of explaining why you think they are wrong, try to understand their logic by asking questions and listening attentively to their responses.

For example:

  • That’s an interesting perspective. Why do you think that?
  • How do you think your views on [the subject] have changed over time?

Even if you completely disagree with someone, you can still have a deep and rewarding conversation if you show each other respect.

If the discussion gets too heated or is no longer enjoyable, end it graciously. You could say, “It’s been fascinating to hear your views. Let’s agree to disagree,” and then change the topic. Or you could say, “It’s interesting to hear a totally different perspective on [the subject]. I don’t agree, but it’s been great to have a respectful conversation about it.”

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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.

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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 ?

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