The Manly Man’s Guide to Deep Conversation Topics with Friends

Dudefluencer: Deep Conversation Topics with Friends

Let’s face it, you’re a manly man. Everyone knows you like sports, Metallica, and beer. But you’re still missing something, you want those close male friendships and have no idea where to start. Thankfully I am here, a fellow manly man, to guide you to explore deep conversation topics with friends.

The challenging part of starting a deep conversation with your friends is in the build-up, and the moments before you bring up those difficult, introspective topics. But remember the most successful men in the world harness the power of these three things: courage, community, and communication. And engaging in deep, meaningful conversations with your friends hits all three of those commonalities.

To take part in deep conversation topics with friends, there is a level of courage involved. You need to be vulnerable, you need to be introspective. By engaging in meaningful dude chats, you’re helping build a community and brotherhood. And obviously, you’re practicing those all too important communication skills.

What is considered a deep conversation topic?

Men often have shoulder-to-shoulder friendships, which means our conversations with other dudes tend to be shallow and surface level. For example, if you’re at the bar and arguing over who the most significant power forward in NBA history is, that’s a surface-level question. If you’re talking about your partner and only how hot they are, that’s a surface level conversation. Heck, if you ask your friend what they have been up to and respond with “work-stuff” and nothing else, congratulations, you just had another surface-level conversation.

That isn’t to say those conversations are bad: to build deeper relationships with other dudes, it’s essential to have those light, breezy discussions to start with. Just remember, small talk doesn’t build relationships.

So what is considered to be a deep conversation? Deep conversations are those conversations that require courage. Maybe you need to be a bit reflective or vulnerable. Perhaps you need to confront a challenging topic you’ve been avoiding. As long as you have a supportive community and bountiful courage, your communication skills will lead you to more fulfilling relationships with your friends.

A simple way to differentiate small talk from more in-depth conversations is to think about it this way: small talk is about topics and events, and more detailed discussions are about ideas and beliefs. By transitioning from small-talk to substantive conversation topics with friends, you’re going to be on the path to building a healthy community of dudes who will lift you up to your full potential.

But why?

Everyone loves small-talk, right?

Not exactly. A 2010 study published by Psychological Science revealed that happier people tend to have twice as many deep and meaningful conversations than those who are unhappy. Many people highlighted that small-talk and networking were exhausting. Yet, when invested in these deep conversation topics with friends, there was an element of community building. If you haven’t picked up on this idea, however, yes, community building is essential to every man’s success and happiness.

In an interview with the New York Times, Matthias Mehl (a contributing researcher on the study), said that substantial conversations are the key to happiness for two reasons, “By engaging in meaningful conversations, we manage to impose meaning on an otherwise pretty chaotic world. And interpersonally, as you find this meaning, you bond with your interactive partner, and we know that interpersonal connection and integration is a core fundamental foundation of happiness.” By finding meaning and connection, deep conversation topics with friends might be the difference between happiness and sadness.

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The Manly Man’s Guide to Deep Conversation Topics with Friends

Suppose you’re still struggling to figure out how to lead deep conversations with your friends. In that case, Marcel Schwantes has two keys to help you out: “1) showing curiosity in the other person (which is reciprocated), and 2) choosing captivating questions to ask.” That’s it. All you need to do is be present and listen, which is no different from how you build better communication in your relationships and have substantial questions in your back pocket.

Our guide can’t tell you how to be more present, or how to be a better listener, that’s something you need to invest in yourself. But, The Manly Man’s Guide to Deep Conversation Topics with Friends can certainly point you in the right direction for choosing a variety of captivating questions that can lead to building stronger relationships and increasing your personal happiness.

Organized by topics, not only do we feature some of the best questions/conversations starters, but also why and when you use them. And unlike other conversation topic guides, we are only including the conversation starters that make sense in a normal conversation, rather than a topic that comes out of nowhere.

Let’s talk about success.

Successful men find ways to celebrate achievement, no matter how small the success might be. Whether it’s mustering up the courage to have an awkward conversation, or taking the next step in starting a business, supporting other men while they are achieving their goals is essential to secure community building. So when thinking about deep conversation topics with friends, starting off with discussions around achievement are easy wins.

Conversation Starter: “Congratulations on completing [project], I’d love for you to tell me more about your work on it.”

The project can be replaced by nearly any accomplishment, it doesn’t matter. You congratulate your friend on their success, and more importantly, open the door for them to talk more about their project. Remember, the key to substantive conversations amongst friends is the willingness to listen, and have a genuine curiosity about what they are talking about.

The best part of this conversation starter is all of the different angles it can go: you can then both discuss your projects or, better yet, lead this into a conversation about your futures. One of the best ways to build a stronger bond between two people is to discuss your goals, your next steps, and how you can best support them on their quest.

Again, don’t just high-five your friend, or buy them a beer. Be curious and allow them to show off a bit. They succeeded, they just took a step to the next level. And dudes who surround themselves with dudes who play at a higher level are always more successful.

Conversation Starter: “What was the hardest part of accomplishing your goal?”

Succeeding at a goal provides lessons, but the most important lessons anyone can learn is from failure. By asking your friend about the hardest part of their success, you’re not only acknowledging their success but also allowing them to open up about some of the difficulties of their process. This might require your friends to become introspective, and really think about what they accomplished.

For you, this also is a learning experience: learning from other failures can be a great lesson towards accomplishing your own goals. So remember to be attentive, and ask follow-up questions.

This is one of those deep conversation topics for friends that really allows both of you to interact with each other and do some great community building. It also requires a little bit of courage since masculinity often tells us that failure is negative. You can even throw this question out there after the previous one. Hopefully, it will lead to a fulfilling dialogue.

Deep Conversation Topic: Where do you plan to go from here?

There are two human needs that every successful person on Earth seeks out: growth and contribution. There needs to be time to celebrate success, but it’s also a good idea to think about what’s next. That’s why if you’re looking to find deep conversation topics with friends, the future is always a brilliant topic to bring up.

Why? Well, who doesn’t love envisioning more success, more accomplishments? Do you think Michael Jordan ever looked at his NBA trophies and said, “You know, one was enough.” Heck no. By introducing the idea of future planning and goal setting, you build a community that is ready to support and hold each other accountable.

Conversations around health and wellness.

For men, we struggle to open up about our mental health. Thus we are often left to suffer in silence or put all of our emotional baggage on our partners. We don’t want to be emotional golddiggers any longer. Maybe it’s time for all men to start opening up about their mental health and how they’re feeling.

Conversation Starter: “Hey, I’ve noticed something is off. I just want you to know that I support you, and I’ve got your back for whatever you need. I’m happy to talk when you’re ready.”

We never want to assume something is wrong with our friends, but dudes know their dude community pretty well and can tell when something is off. But instead of ignoring the problem, your friend might be looking for someone to throw them a lifeline of conversation.

Here is a simple way to let your friend know that you care, while also giving them the space to talk about it if they so choose. Remember, the strength and success of a man is representative of the community of men around him. This little conversation starter reminds your friend that they are supported. Most importantly, you are ready to listen when they are prepared to talk.

Unlike many other conversation starters, this might not lead to an in-depth conversation right away. Still, it does build the foundation for something further down the line. And most importantly, it’s not pushy.

Conversation Starter: Let your friends know what you need from them.

This is for you to introduce the topic of your health when you’re ready for support. Before you go into a conversation, think about what you want from your friends and how they can best provide that. From my experience, whenever I’ve needed support, my group of dudes has always been there because they love and care about me.

For example, this might be a way to let your community know you’re not feeling okay and allow them to step up and support you. This particular deep conversation topic requires two of the three essential C’s of successful men: communication and courage.

Courage comes from opening up about a personal subject, and communication in that you must be able to articulate what you’d like from your community. Maybe you’d like to see them soon for a drink or dinner, perhaps you’d love to just FaceTime them. Communicate a clear expectation and watch how the people who love you engage, show empathy, and ultimately encourage you to be the best version of you.

Deep Conversation Topic: How does masculinity affect men’s ability to seek help and support each other in times of health crises?

So definitely don’t start out your conversation like this, but having dudes talk about masculinity and its effects on their health can lead to some amazing breakthroughs. This allows you and your friends to have an in-depth conversation about how manhood is involved in their decision-making while also opening the door for how to best support each other.

I’m often reminded of the research that came from a men’s support group for older cancer survivors: they all talked about how they wished something like this existed earlier while also holding back from completely being 100% vulnerable. A short conversation with your dude community about men’s health and supporting each other could go a long way in destigmatizing asking for help.

The power of gratitude.

There’s power in investing in gratitude. It’s more than just a thank you, gratitude is about embracing the best parts of your life. Gratitude also promotes more social behavior, which makes people more engaged and valued. But too often men forget about the benefits of gratitude, or worse yet, ignore them. If you’re looking for deep conversation topics with friends, start thinking about the power of thank you.

Conversation Starter: “I want you to know I appreciate our friendship, and I’d love to talk to you soon.”

This is the conversation starter for those friendships you may have let slip away, or time/distance/life has made challenging to keep up with. I like to believe that every friendship gives us something: whether it’s happiness, love, or lessons, most bonds are worth it. I recently had a moment where I reached out to some people I was close to but hadn’t spoken with in years. It was vital for me to let them know how much I appreciated our time together.

If you’re looking to rekindle a friendship, this is one of the better ways. This particular deep conversation starter allows you to do two things: one is to let your friend know you care about them, and secondly, allows for conversation easily. You can start by reminiscing, asking about their life, and a whole myriad of topics. The significant part is the “I’d love to talk to you soon,” because, without that, there is no indication you’d like this conversation to go on longer.

A conversation starter like this requires courage to be willing to put yourself out there and be vulnerable in the face of rejection. But remember, courage is doing the difficult action even if you’re afraid.

Conversation Starter: “What’s the best thing that happened to you today?”

I’ve seen this question asked as an icebreaker at parties before. The conversation starter is simple in its premise but allows for a lot of depth if you are willing to go further. By asking this question, you’re asking someone to think back on their day to find something to be grateful for and give them the power of gratitude.

This conversation starter is even one you should ask yourself: be reflective, be introspective, be grateful. Suppose you’re talking about what you’re thankful for in conversation. In that case, this allows both parties to be curious listeners and encourages follow up questions.

You can learn a lot about somebody by the way they talk about gratitude. We want to surround ourselves with people who will push us while also doing their best to live in a positive state. Use this conversation starter as a way to build a stronger community.

Deep Conversation Topic: How can we show gratitude towards the worst life has challenged us with?

Asking this question to friends and yourself requires a lot of courage. You need to reflect on yourself, your beliefs, and those trying times in your life. And if you’re asking this question? You better be prepared for your friends to be a bit dismissive or avoidant altogether.

That’s because no one wants to reflect on the difficult moments of their life, let alone find things to be grateful for within them. For example, I was resistant to reflect on my first long-term relationship because I had told myself a narrative about what it all meant. All of the lessons I learned were harsh, negative, and honestly, unproductive. After one conversation with Rachel, she forced me to reflect and look at the relationship’s real positives. The positive ways it forced me to grow.

Like you and your friends, I didn’t want to revisit the past, but I can now sit here (behind my computer screen) and tell you that I am a better person. When you are ready to push your friends and take the next step, it might be an excellent time to encourage some deep reflection.

How can we motivate our peers?

What are the three C’s behind every successful man? Community, communication, and courage. If you’re looking for the best way to get motivated, find yourself a group of dudes who want to help push you towards success, and always have your back. A strong community can be one of the biggest motivators, especially if you’re all willing to invest in some of these deep conversation topics with friends.

Conversation Starter: “What’s your biggest motivator?”

This is another one of those conversation starters that works well as an icebreaker, as well as opening up to a more in-depth conversation. Think about how this question can then initiate conversations about future plans and goals. When someone has to think about their greatest motivator or what drives them, you’re asking them to share an essential part of themselves with you, thus creating a substantive conversation.

Talking about motivators and drive also allows your friend to share new information with you, and provides an opportunity for community building. Maybe you have a similar goal, or drive? Whatever it is, don’t forget to bring up follow-up questions.

Your friend should also be asking questions if this is going to be a candid conversation. Allow them to lead the discussion at times and not be afraid to ask those more profound, more exciting questions.

Conversation Starter: “What are the next steps you can take, and how can I help?”

This is similar to the “What comes next” question but is a bit more straight to the point. When you’re asking your friend about their next steps, and how you can help, you’re directly offering them a lifeline to complete their goals and ask a genuine question.

From here, the conversation can go multiple ways. Like always, you want to listen intently. Maybe they don’t want any help, they just want someone to listen. Or possibly they’ve been waiting for this moment and have been too prideful to ask. No matter what, listen to what they are saying and respond accordingly.


Introducing deep conversation topics with friends can be challenging: it requires all three C’s of successful men: community, courage, and communication. But trust me, once you’ve built up all three of those skills, building substantive conversations will lead to deeper, more meaningful relationships.

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