Why Is It So Hard to Have Deep Conversations With Men? (From a Guy)

As a dude, I can count on one hand the number of times I've had a genuinely deep, vulnerable conversation with another guy.

We talk about sports, video games, work, maybe dating. But feelings? Fears? Struggles? That stuff almost never comes up.

And for years I thought that was just how male friendships worked. Turns out, we're all just following some unspoken rules that are making us lonely as hell.

The Surface-Level Friendship Problem

I have friends I've known for like 15 years. I could tell you their favorite sports team, what they do for work, their girlfriend's name.

But I couldn't tell you what they're actually scared of. What keeps them up at night. What they're struggling with.

Because we just... don't talk about that stuff.

When I Realized This Was a Problem

Last year one of my close friends told me he'd been struggling with depression for over a year.

I had no idea. We hung out regularly, texted in the group chat, played games online. And I didn't notice he was suffering because we never talked about anything real.

That messed me up. How could I call him a close friend when I didn't even know he was in pain?

Why Guys Don't Go Deep

After alot of thinking (and some therapy, which yeah, I was nervous to admit I was doing at first - proving my own point lol), I figured out why men struggle with deeper conversations:

We're Taught Emotions Are Weakness

From childhood, guys get the message that showing emotion is weak or feminine. "Boys don't cry." "Man up." "Stop being so sensitive."

So we learn to suppress that stuff. And then as adults, we literally don't know how to access or articulate our feelings even when we want to.

Vulnerability Feels Dangerous

Opening up to someone means risking rejection, judgment, or losing respect. And that risk feels way higher with other men than it does with women (in my experience anyway).

If I tell a guy friend I'm struggling, part of me worries he'll see me as less capable or less masculine. Which is ridiculous, but the fear is real.

We Don't Have Role Models for This

I've never seen my dad have a deep emotional conversation with another man. Most movies and shows depict male friendships as surface-level or joke-based.

We don't have examples of what vulnerable male friendship even looks like. So we don't know how to do it.

The Jokes Defense Mechanism

Anytime a conversation starts getting real, one of us makes a joke to lighten the mood. It's like a reflex.

Someone's sharing something vulnerable? Time for a sarcastic comment or a subject change disguised as humor.

We use jokes as a shield against actually connecting.

Fear of Being "That Guy"

Nobody wants to be the guy who makes things awkward by getting too serious or emotional. Better to keep it light than risk being seen as intense or needy.

What This Costs Us

This surface-level friendship thing isn't harmless. It's actually destroying us.

We're Lonely

Men report higher rates of loneliness than ever before. And I think a big reason is because our friendships don't provide real emotional connection.

You can be surrounded by "bros" and still feel completly alone because none of those relationships go below the surface.

We Don't Have Support Systems

When shit gets hard - breakups, job loss, mental health struggles, family stuff - alot of guys have nobody to actually talk to about it.

We're expected to just handle it alone. Which is why male suicide rates are so high. We're isolated in our pain.

We Don't Know Ourselves

If you never talk about feelings, you don't develop emotional intelligence or self-awareness. You just go through life kind of numb and disconnected from yourself.

I spent years not even knowing what I was feeling because I'd suppressed it for so long.

Our Relationships Suffer

This inability to be vulnerable and communicate emotionally doesn't just affect friendships. It destroys romantic relationships too.

How can you have a healthy partnership when you can't articulate what you need or how you feel?

My Attempts to Change This

After my friend's depression revelation, I decided to try having deeper conversations with the guys in my life. Here's what happened:

Attempt 1: Epic Fail

I tried to initiate a deep conversation with a friend while we were playing video games. Asked him if he was happy with his life.

He laughed it off and made a joke. I pushed a little more. He got uncomfortable and changed the subject.

It was awkward. I felt like I'd broken some social rule.

Attempt 2: Slightly Better

I was hanging out one-on-one with another friend and mentioned I'd been going to therapy. Tried to keep it casual but honest.

He seemed genuinely interested and shared that he'd been thinking about going too. We had like a 5-minute real conversation before defaulting back to safer topics.

Small progress.

Attempt 3: Actual Breakthrough

I was hiking with a friend and he mentioned he'd been stressed about work. Instead of just saying "that sucks man" and moving on, I asked follow-up questions.

"What specifically is stressing you out? How's that affecting you? What do you think you need?"

He opened up. Like actually opened up about imposter syndrome and anxiety and feeling overwhelmed. We talked for probably an hour about real stuff.

It felt... really good? But also kind of uncomfortable because it was so unfamiliar.

What I've Learned About Having Deep Conversations with Men

Create the Right Environment

Deep conversations happen easier during activities - hiking, driving, working on something together.

The side-by-side thing makes it less intense than sitting face-to-face. Guys tend to open up more when there's something else to focus on.

Start Small

Don't jump straight to "tell me about your childhood trauma." Start with slightly deeper than usual questions.

"How are you actually doing?" (with emphasis on actually)

"What's been on your mind lately?"

"That sounds tough, how are you handling it?"

Go First

Vulnerability breeds vulnerability. If you want someone to open up, you usually have to go first.

Share something real about yourself and give them permission to do the same.

Don't Make a Big Deal About It

If a guy does share something vulnerable, don't be like "wow thanks for opening up, this is so great, we're having a deep conversation!"

Just... receive it normally. Ask follow-up questions. Treat it like a regular conversation.

Making it a big deal makes it feel weird and makes them less likely to do it again.

Skip the Jokes (Sometimes)

This is hard because humor is our default, but sometimes you gotta just sit in the seriousness.

If someone's sharing something real and you immediately crack a joke, you're shutting down the vulnerability.

Normalize It Over Time

The more you have deeper conversations, the more normal it becomes. You're literally creating a new pattern in the friendship.

The first few times will be awkward. But eventually, it becomes part of how you relate to each other.

The Friendships That Changed

I now have a small group of guys I can actually talk to about real stuff. And it's completly changed my life.

What's Different

It's Still Not Perfect

We still talk about sports and games and surface-level stuff most of the time. And that's fine - not every conversation needs to be deep.

But now there's an option for realness when we need it. And just knowing that option exists makes a huge diference.

To Other Guys Who Want Deeper Friendships

You're not weak for wanting emotional connection. You're not weird for being tired of surface-level friendships.

And I promise, alot of the guys in your life probably want the same thing but don't know how to initiate it.

Be the One to Start

It's scary, but someone has to go first. Might as well be you.

Next time a friend mentions something hard, don't just say "that sucks" and move on. Ask questions. Show you actually care about the answer.

Find Guys Who Are Open to It

Not every guy is ready for deeper friendship. Some are too locked into the traditional masculinity thing.

That's okay. Focus on the friends who respond to your attempts at vulnerability. Build those relationships.

Work on Your Own Emotional Awareness

You can't have deep conversations if you don't know what you're feeling or how to articulate it.

Therapy helped me alot with this. Journaling. Books about emotional intelligence. Learning the actual vocabulary for emotions beyond "fine," "good," and "stressed."

Be Patient

This is awkward because we've been trained our whole lives to avoid this kind of connection. It takes practice.

The first attempts will probably be uncomfortable. That's normal. Keep trying.

Final Thoughts

Male friendship doesn't have to be shallow. It shouldn't be shallow.

We deserve relationships where we can be fully known, where we can be vulnerable, where we can actually support each other beyond surface-level banter.

But that requires someone to break the pattern. To risk the awkwardness. To model a different way of connecting.

So if you're a guy reading this and nodding along, thinking "yeah, I want deeper friendships too" - start the conversation.

Ask better questions. Share something real. Be willing to sit in discomfort.

Your friends need it just as much as you do. They're just waiting for someone to make it okay.