A Man's Guide to Maintaining Friendships
If you want strong relationships later in life, you have to build them intentionally now.
Hi, I’m Chris. I’ve spent the last 25 years building businesses, wealth in real estate, and learning what actually matters along the way. Most people don’t fail; they drift. Here, I share how to create wealth and live a life that doesn’t decline.
Three years ago, when my dad died, I realized something most men don’t think about until it’s too late. In the hardest moments of your life, you do not suddenly create friendships. You discover the ones you already invested in.
My phone filled with messages from people across every season of my life. Childhood friends. Business relationships. Guys from the gym. Friends from our community. And every one of those relationships existed because someone kept reaching out over the years, even when there was no crisis.
Most men never treat friendship like something that needs maintenance. They pour themselves into work. Marriage. Kids. Achievement. Responsibility. Friendship slowly slides to the bottom of the list because it never feels urgent.
Until one day, they look around and realize they built a successful life with almost nobody left inside it. Many men are waking up relationally broke.
I run multiple companies. I have a full schedule, a family I care deeply about, and more responsibilities pulling at my attention than I can possibly get to in a day. There is always another meeting, another project, another deadline competing for my time.
Modern life is remarkably good at making us believe friendship is optional, right up until the moment we desperately need it.
One day, the roles shift. Careers change. Kids grow up. Parents pass away. A divorce happens. A health issue changes everything. Suddenly, a man looks around and realizes how much of his relational world was tied to structures and seasons that no longer exist.
So the question becomes a practical one: how do you actually build and maintain meaningful friendships in midlife?
Proximity Used to Build Friendship for Us
When we were kids, friendship happened naturally because the environment did most of the work. School put us in the same rooms every day. Sports teams gave us shared goals. Neighborhoods kept us physically close. We saw the same people over and over without needing to schedule anything. Proximity created familiarity, and familiarity created friendship.
As we age, that infrastructure quietly disappears. Nobody automatically puts men in environments where deep friendship develops anymore. Modern life replaces those spaces with schedules, screens, and exhaustion. Most men are not rejecting friendship. They are drifting away from the conditions that once made it easy.
That means friendship now requires intentionality. And it starts with understanding how male friendship actually works.
Men Bond Shoulder to Shoulder
One of the biggest mistakes men make is thinking connection has to look emotionally intense to count. It does not. Most male friendships are first built side by side, not face-to-face.
University of Maryland researcher Geoffrey Greif, in his book Buddy System, argues that male friendships tend to be “shoulder to shoulder” rather than “eye to eye.” Men bond while doing things together, not by sitting across from each other and processing feelings.
NYU developmental psychologist Niobe Way spent decades interviewing boys and men about friendship. Her research found that boys start out craving close connection, and then cultural pressure gradually teaches them to suppress it. The capacity for friendship does not disappear. It gets suppressed and only finds its way back when trust has been built over time.
What builds that trust is what researchers call “the in-between.” It is not the activity itself that does the bonding. It is the unstructured time surrounding it: the ride over, the cooldown after a workout, the beers after the game, the parking-lot conversation nobody quite wants to end.
In those low-stakes, agenda-free moments, idle conversation gradually transforms into real connection. You are not trying to connect; you’re filling silence with who you are, and that accumulates into something lasting.
Men, this is actually simpler than you think. You do not need to manufacture vulnerability or force deep conversations. You need consistent proximity. Shared experiences. Repeated time together.
Just do life alongside other men you respect. Then do it again next week.
Building and maintaining friendships in midlife looks like weekday early morning workouts. Hiking with the same group every few weeks. The annual trip everyone actually prioritizes and shows up for. The group text thread about your favorite sports team that stays alive. The extra thirty minutes standing in the parking lot talking.
These are not small things. They are the structure holding your relational life together.
A lot of men wait for deep conversations first, as if emotional connection is the entry fee to friendship. But the research, and my own experience, says it usually works the other way around. The depth comes after the shared time, not before.
Someone Has to Go First
I sent a text to a friend recently that I had been meaning to send for months. We had not talked in at least a year as life had gotten busy for both of us. The whole exchange took a few minutes. He was happy to hear from me, and we had plans within a week. I had been overthinking it for months.
That is how this usually works.
At some point, friendship stops happening automatically and starts requiring someone to lead. Someone has to initiate. Someone has to text first. Most people are quietly hoping someone else will go first, and so nothing happens.
Be the guy who goes first.
I know reaching out can feel vulnerable in a way it never did when you were younger. There’s risk in it. What if they say no? Underneath much of male isolation is something that most people don’t see: most men assume the other guy is too busy or uninterested, when research shows people consistently underestimate how much others actually want connection.
Friendship Compounds the Same Way Money Does
The biggest mistake men make is underestimating the power of small, repeated investments over time. Friendship compounds exactly the same way wealth does: slowly, consistently, and almost invisibly at first. Which is also why it disappears so easily. Most men assume there will be more time later. Later, when work calms down. Later, when the kids are older. Later, when life slows down.
But life rarely slows down on its own.
The men you spend the most time with shape you, whether you realize it or not. Their standards affect yours. Their habits affect yours. Their ambition, discipline, marriages, mindset, and emotional health eventually influence your own life too. That is why friendship matters more than most men think it does. You do not just need people around you. You need men who sharpen your standards, challenge your thinking, and call you toward a better life.
Start Bold: Reach Out Now
You know those friends you haven’t talked to in years? High school friends. College friends. People you used to work with, live near, coach with, or play ball with who gradually drifted to the edges while life kept moving. You think about them sometimes. You mean to reach out. But modern life is very good at convincing men there will always be more time later.
Do not wait for a crisis, a funeral, or a major life event to reconnect.
Start now. Send the text. Make the plan. Some of your closest friends may still be out there, waiting for you to invite them again.
Yes, it might feel awkward. Yes, it has been a long time. My aunt used to say that friendships are like a good book: you can pick right back up where you left off. She was right. The conversation finds its footing within minutes, and the years dissolve quickly when someone actually reaches out.
The men who still have deep friendships later in life are usually the ones who built it long before they needed it.
Your Turn + Start Bold
Three things to do this week:
Text one person you’ve been meaning to reach out to. Do not overthink it.
Put one recurring thing on the calendar with a friend, whether it is a workout, a coffee, or a monthly breakfast. Repetition is the foundation.
Comment on this post. I’d love to connect with you.
Don’t drift; live boldly.
Hi Chris, men do not talk enough about a lot of topics and this is an especially important one as you have highlighted. I find the impact of what you are saying, more powerful when it is followed with actionable items.
We do not allow ourselves to open up and build that group of close relationships that we took for granted when we were younger. We are not too busy, we are too distracted and fearful and let too many other people weigh in on our life. I am very much looking forward to meeting you for both personal and professional reasons. My partner has created an exciting and rewarding program called Dust and Leather - where men can come to our farm and experience the nostalgia of a Cowboy and the deep connection through Horsemanship with horses. A small group of men experiencing the toughness of a hard and rewarding days work all while connecting with an animal that can feel your heartbeat from 4ft away and size you up before you ever enter the arena.
Michael
Thanks, again, Chris. YES! Several terrific observations and suggestions.