What We’re Really Longing for in Midlife Friendships
As I sit here writing this, I can’t help but think about the incredible power friendship holds – especially as we navigate midlife. It’s one of those deeply transformative forces that can truly change the game, don’t you think?
In midlife, many of us find ourselves reevaluating relationships and questioning what we really need in our circles. Genuine friendship – the kind that goes beyond the surface – isn’t just a luxury; it’s a lifeline.
And yet, the busyness of life and shifting priorities can make it feel like we’re floating on the edges of our social lives, wishing for something deeper.
What if the friendships we crave are simply waiting for us to show up for them?
That’s what this post is about: the power of genuine friendship in midlife, and how it can transform not only your connections – but your entire sense of self.
When Friendship Feels Shallow (and Why it’s Not Your Fault)
As we enter midlife, it’s easy to feel disconnected, even when surrounded by people. We juggle careers, families, and endless to-do lists. Amid all this, how do we build friendships that are not only real, but also uplifting and full of joy?
For me, it’s been a journey of rethinking what it really means to be a friend – and what it takes to invite genuine connection into my life. It’s more than meeting for coffee or chatting about the weather. It’s about going deeper – being vulnerable, being seen, and allowing others to do the same.
Throughout my life, I’ve had friendships that didn’t quite measure up.
I’ve trusted the wrong people, let my guard down, and ended up hurt. I’ve been disappointed by those who didn’t show up when it mattered, who pretended to be friends but weren’t. And for a long time, I couldn’t figure out why I kept feeling drained and unseen by the very people I called friends.
The Shift:
At first, I blamed them. It’s them, not me. But it wasn’t until recently that I realized something big: the way I was showing up for myself directly influenced the relationships I was drawing in.
As a life coach, I would’ve spotted this pattern in a heartbeat with my clients. But, of course, it’s like the shoemaker whose kids have no shoes, or the doctor who counsels patients on a healthy lifestyle and then sneaks a cigarette on her break – applying these insights to my own life? Another story entirely.
Don’t get me wrong – I’ve been fortunate to have some amazing friends. But it wasn’t until I started investing more in myself – treating myself with kindness, setting healthy boundaries, and showing up for me that my friendships began to feel stronger and more fulfilling.
And the real breakthrough?
As I started being my true self, I attracted others who were doing the same.
This year, I made a simple promise: to treat myself the way I wanted others to treat me – with respect, love, and a little more grace. It wasn’t some big “aha” moment, but rather a slow realization that I was worth the care I was giving others. And once it started, everything began to shift.
Genuine Friendship Starts with Being Your Own Best Friend
If you want genuine friendships, start with the most important one – the one with yourself. When we nurture self-connection, we create space for authentic connection.
Because friendship is an energy exchange – and the energy we bring shapes what we attract.
Ask yourself:
What would it look like to be a better friend to yourself?
Try This: Strengthen a Friendship
This week, reach out to one person you consider a true friend and tell them something you value about them.
It could be as simple as:
“I really appreciate how supportive you are.”
“You always make me laugh when I need it most.”
And if no one immediately comes to mind, start with you.
Take a moment to tell yourself something you value about yourself – whether it’s your kindness, resilience, or your ability to show up for others.
We often forget to show ourselves the same appreciation we offer others. But this small act of self-love can help remind you of your own worth, while also nurturing the friendships that matter. Real friendship – with ourselves and others – begins there.
When it comes to friendship, it’s not about how many people you know – it’s about how deeply you connect with the ones who matter.
When’s the last time you felt truly seen by a friend?
“Friendship is born at that moment when one person says to another, ‘What! You too? I thought I was the only one.” — C.S. Lewis
About the Author – Making Midlife Funderful


Cheryl Dillon, CPC – Life Coach & Founder of Funderful Experiences
Cheryl Dillon is a life coach, writer, and founder of Funderful Experiences, home of the Connected Hearts membership – a community helping women shape a midlife that feels joyful, vibrant, and fulfilling. She’s also the creator of The Uplift, a nationally read newsletter that blends storytelling, coaching, and humor to help women reconnect with themselves and each other – bringing more laughter, purpose, and heart to everyday life.
Cheryl’s work centers on the belief that genuine connection, meaningful experiences, and fun have the power to redefine the midlife experience. With a background in psychology and coaching, she brings a refreshing mix of real talk, warmth, and wisdom to conversations about friendship, identity, and self-renewal.
More Real Talk
The Courage to Be Seen: How Authenticity Builds Real Connection in Midlife
It’s Not Too Late to Try Something New


