Navigating Your Son’s First Heartbreak

A boy’s first real heartbreak can take almost any form. It may be the ole unrequited playground love or the death of a grandparent. Maybe it’ll be a move across town, or being caught amidst his parents’ divorce that’s coaxing his tears. Whatever the reason behind your son’s heartache, he needs to know that what he’s feeling is OK, and perfectly normal. He also needs to know how to deal with those feelings. 

I’m the father of an 8-year-old boy, which is a lesson in heartbreak itself (it’s also a lesson in a thing called “ROBLOX”, but we’ll leave that for another time). I often look at my little boy and lament the cruel march of time. I know that this little guy’s joyful whimsy will someday give way to guile and cynicism. That his heart will likely break many times throughout his life. It’s inevitable, but it still hurts. That’s why it’s important that we, as fathers, walk our boys through their first heartbreak with patience and understanding.


The best way to navigate the minefield of a little boy’s heart is to help him understand it. It’s your job to get your son through the painful valleys of childhood so he can truly enjoy the amazing views from the mountaintop beyond. You must teach him that his heart is both his most powerful asset and his greatest vulnerability. Understanding these facts are vital for any growing boy. He has to be taught to harness his emotions as one of his superpowers, while having the strength to lick his wounds and move forward when life knocks him down. 

Maybe your father and grandfather swore by the old time-honored tradition of burying their feelings deep down inside, where only Jack Daniels could reach them. But odds are, those feelings never actually went away. They just manifested in other, likely damaging, ways; possibly even limiting their capacity to connect with their own sons. That’s why it’s so important that we remind our little ones that letting their negative feelings out is the first step to getting past them. If your son needs to cry, let him cry. If he wants to talk, be there to listen. If he prefers silence, don’t force a conversation. And if he just wants to cling onto you, hold on tight. 

Whatever his feelings are, encourage him to express them, without judgement. The first thing you must do is just listen. There will be plenty of time for advice, but if he doesn’t get used to expressing negative feelings early on, he’ll struggle with them his entire life.


Once your little guy has verbalized exactly what he’s going through, you’ll need to take more of an active role in helping him face his negative emotions. Remind him that sadness can be constructive. It can teach him a lot about himself, and ultimately help guide him toward healing. 

If he recognizes and accepts his sadness, then he can also discover what heals it. For some kids, laughter is the greatest weapon they have against pain. For others, it may be playing with friends or watching movies with siblings. It’s important to teach him the difference between cultivating happiness in tough times and just ignoring his pain with distractions. There is a distinction.


Your little boy’s heartache can also be the first step to teaching him about empathy. Tell him that he should never be careless with the hearts of others. Remind him that when a friend is sad, he has the power to help them feel better. Developing empathy in a young boy leads to a lifetime of protecting others and spreading joy. Teach him that he can help others to avoid feeling how he’s feeling right now, and that doing so is a noble pursuit.


Your little boy’s first instinct may be to close himself off so that he won’t have to feel this way again. He may decide that he’s going to avoid crushes in the future, or maybe spend less time with remaining grandparents for fear of losing them. That’s a recipe for a lonely life. Boys need to be taught that dealing with their pain in a healthy way is what leads to the true enjoyment of their best days. Avoiding heartbreak altogether will only cause your little one to avoid everything that makes life such a messy, wonderful adventure!


By modeling healthy behaviors in relation to negative feelings, you’ll lead by example, which is always the best kind of teaching. And as your son grows up, he’ll in turn be there with you for your own heartbreaks as well. Grief, disappointment, and illness are unescapable for us all. He’ll admire you for displaying your own vulnerability, emotional intelligence, and resilience. It will prove to him that you practice what you preach, and he’ll be there to offer you the support you need when the time comes.

Your son will eventually grow up. When he does, he’ll need the strength to manage his sadness as he starts to feel the dull pain of time’s relentless march on you. If you’ve given him the tools he needs to keep moving forward, you can rest assured that he’ll be OK, even when you’re no longer there for him. And that’s the greatest hope any father can have for his little boy.