"Awkward" Conversations with Your Son - Why They Matter More Than You Think
Talking to your son about the tricky things like emotions, friendships, relationships, sex, drugs, or mental health can feel uncomfortable for any parent or carer. Most of us already know these conversations matter, but knowing how to start (or when to start) is another thing entirely. And honestly, that’s normal.
At St Augustine’s College, we try to see these moments a little differently. They’re not just awkward hurdles to tiptoe around - they’re meaningful opportunities. When boys learn to talk openly about how they’re feeling, what they’re experiencing, or what they’re curious about, they’re building resilience, emotional awareness, and trust. These things become the foundation of good relationships and strong character later on.
Why These Conversations Matter
If we don’t keep the door open to these topics, young people will often look for answers elsewhere. Sometimes that means friends who are still figuring things out themselves, or online spaces that don’t always offer advice that’s healthy or kind.
Your voice - steady, warm, and grounded - is one of the strongest influences in your son’s world. Even if he doesn’t show it (and sometimes he really won’t), he’s listening.
Making Those “Awkward” Moments Feel a Little Easier
Here are a few simple ways to help these conversations feel more natural:
- Choose the right moment
The best chats often happen when you’re side by side: in the car, walking the dog, or working on something together. Without the formality of “we need to talk,” boys are far more likely to open up. - Ask open, curious questions
Try gentle prompts like, “What did you make of that?” or “How would you have handled it?” They’re the kind of questions that invite reflection instead of one-word answers. - Really listen
Simple things - nodding, reflecting back what he’s said, or acknowledging how he might be feeling - show that you’re taking him seriously. It tells him his voice matters. - Be there for the little things
Often, boys test the waters with offhand comments or tiny stories from their day. When you take those moments seriously (“Oh, that sounds frustrating”), you’re signalling that the bigger things are safe to bring up too. - Don’t rush to solve everything
It’s tempting to jump straight into advice mode, but sometimes boys just want to be heard. Thank him for sharing, sit with it for a moment, and then offer help if he wants it. - Give him space when he needs it
If he shuts down, that’s okay. Let him know you’re around when he’s ready. The real conversation often happens later - sometimes much later. - Share a little of your own experience
A touch of vulnerability helps boys understand that mistakes, questions, and uncertainty are all part of growing up - for everyone. - Keep the conversation going
These chats don’t need to be big, dramatic talks. Lots of small, gentle conversations over time build a culture where nothing is “too awkward” to bring up.
Building Trust, One Conversation at a Time
Even when these conversations feel clumsy (and they will), they remind your son that you’re in his corner. They tell him that home is a safe place to ask questions, share worries, and speak honestly about what he’s facing.
At St Augustine’s College, we aim to nurture young men of heart and purpose - young men who communicate openly, think critically, and care deeply for themselves and others. When these conversations begin at home and continue through school, boys learn that talking about the tough stuff isn’t a sign of weakness. It’s a sign of strength.
