Let's be honest, talking to your son about emotions probably feels about as comfortable as wearing a tuxedo to the beach. You know it's important, but every time you think about bringing it up, you get that same feeling you had before your first job interview: sweaty palms and a brain that suddenly forgets how words work.
Here's the thing though, that awkwardness you're feeling? It's actually a good sign. It means you're stepping outside the box that many of us were raised in, where "real men" kept their feelings locked up tighter than Fort Knox. Your son needs to see that men can talk about emotions without the world ending, and yes, it starts with you.
Why This Matters More Than Ever
We're raising boys in a world that's finally waking up to the fact that emotional intelligence isn't just a "nice to have": it's essential for healthy relationships, career success, and overall wellbeing. But here's what makes it tricky: if mum handles all the emotional stuff while dad stays in the "practical advice" lane, we're accidentally teaching our sons that feelings are a woman's job.
Your son is watching how you handle stress, disappointment, joy, and frustration. He's learning what it means to be a man from you, whether you're actively teaching him or not. When you show him that men can feel deeply and express those feelings in healthy ways, you're giving him permission to be fully human.
Breaking Down the Barriers
Most of the awkwardness comes from the unspoken rules many of us inherited: "Boys don't cry," "Toughen up," "Don't be so sensitive." These messages, while often well-intentioned, created a generation of men who struggle to connect emotionally: with themselves and others.
The middle school years can be particularly challenging. Your son might suddenly decide that talking about feelings is "girly" as he figures out his identity as a young man. This is exactly when he needs you most, even if he seems to push you away.
The key is understanding that you're not trying to make your son "soft": you're helping him become emotionally strong. There's a huge difference between suppressing emotions and managing them effectively.
Start With Your Own Story
The most powerful conversations often begin with your own experiences. Instead of diving straight into "How are you feeling?", try sharing something from your own day:
"Work was really stressful today. I had three deadlines hit at once and honestly, I felt pretty overwhelmed. I had to take a few deep breaths and figure out what to tackle first."
This does two things: it normalises discussing emotions and creates a natural opening for your son to share his own experiences. You're modeling that it's okay for men to acknowledge when they're struggling.
Don't feel like you need to have it all figured out to start these conversations. Sometimes the most powerful thing you can say is, "I'm still learning how to handle this stuff too."
Create the Right Environment
Timing and setting matter more than you might think. Some of the best conversations happen when you're both doing something else: building something together, driving in the car, or even just walking the dog.
Activities that work well:
- Working on projects together
- Car rides (something about not making direct eye contact makes it easier)
- Shooting hoops or playing catch
- Cooking together
- Walking or hiking
The key is letting your son lead the activity while you create space for conversation. When his hands are busy, he's often more comfortable opening up.
Practical Conversation Starters
Forget the heavy, sit-down talks that feel like a scene from a serious movie. The best emotional conversations happen naturally:
Instead of: "We need to talk about your feelings."
Try: "That sounded frustrating. Want to tell me about it?"
Instead of: "How do you feel about that?"
Try: "What was that like for you?"
Instead of: "Don't be upset."
Try: "I can see this really matters to you."
Start small. Ask about the best and worst parts of his day. Share your own highs and lows. Show genuine interest in what he cares about, even if it's video games or something you don't fully understand.
Listen More Than You Talk
This might be the hardest part for many dads: resisting the urge to immediately fix or give advice. Sometimes your son just needs to be heard. When he does share something difficult, try responding with:
- "That sounds really tough."
- "Tell me more about that."
- "What do you think might help?"
Save the advice for when he specifically asks for it, or after you've really listened to understand what he's going through.
Handle the Difficult Emotions Too
Don't just focus on the "safe" emotions like happiness or excitement. Your son needs to know it's okay to feel angry, sad, disappointed, or scared. These emotions aren't problems to solve: they're part of the human experience.
When your son is angry, instead of immediately trying to calm him down, try validating the feeling first: "You're really angry about this. That makes sense." Once he feels heard, you can work together on healthy ways to express and manage that anger.
Address Your Own Father Wounds
This one's tough but important. Many of us are parenting with a blueprint from our own fathers who may not have been emotionally available. If your dad never talked to you about feelings, you might not have a roadmap for these conversations.
It's okay to acknowledge this with your son: "My dad wasn't great at talking about this stuff, and I'm still learning. But I want us to have a different kind of relationship."
Sometimes the best thing you can do is get some support for yourself: whether that's reading books about emotional intelligence, talking to other dads, or working with a counsellor.
What About the Eye Rolls?
If your son rolls his eyes or seems resistant, don't take it personally. Teenagers especially are wired to push away from parents as they establish independence. Keep showing up anyway.
Consistency matters more than perfection. Even awkward attempts at connection are better than no attempts at all. Your son will remember that you tried, even if he didn't seem receptive at the time.
The Long-Term Payoff
Here's what you're really building: a son who can handle life's challenges without falling apart, who can maintain healthy relationships, and who won't be afraid to ask for help when he needs it.
You're also building a relationship that can last well into his adulthood. The dads who have close relationships with their adult sons are usually the ones who put in this emotional groundwork early.
When to Seek Extra Support
Sometimes you might feel like you're in over your head, and that's completely normal. If your son is dealing with significant challenges: anxiety, depression, bullying, or major life changes: professional support can make a huge difference.
At Psychology NSW, we work with families every day who are navigating these conversations. Sometimes having a neutral space where both you and your son can learn better communication skills can be incredibly helpful.
The goal isn't to become your son's therapist: it's to be his dad who creates a safe space for him to be fully human. That's a gift that will serve him for the rest of his life, and it starts with your willingness to push through the awkwardness and show up authentically.
Remember, you don't have to be perfect at this. You just have to be willing to try, keep learning, and model what emotional health looks like for the man your son is becoming.
