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How to Make (Real) Friends in Midlife—Without Feeling Awkward

building midlife confidence friends making friends in midlife midlife transition midlife with purpose Jun 12, 2025
Three midlife women enjoying coffee and taking a selfie during a fun friendship outing by the water, smiling and embracing joyful midlife living

If you’ve ever sat in your car before an event wondering, Why did I say yes to this?—you’re not alone.

Making friends in midlife is a whole different ball game. We’re not hanging out with basketball moms or bonding over diapers anymore. Life looks different. If we’re honest, many of us are in a season of change—kids leaving home, careers shifting, relationships evolving.

But here’s the truth:
You weren’t meant to do midlife alone.

Even if you’re enjoying the quiet (hello, finally!), that pull for connection still exists. It just might look a little different now—and that’s okay.

I’m in that season again myself. Recently, I joined our neighborhood pool and went to a local flight club meeting with my partner, Chris. I’ll be honest: it felt awkward at first. But I reminded myself—these small steps are what community begins with.

If you’re craving more connection, here are a few gentle ways to put yourself out there (without forcing anything that feels inauthentic):

1. Start where you already are.

Think about your routines—where do you already spend time? The gym, church, dog park, or library? Strike up a short conversation. A simple “Hey, I see you here often…” can open the door.

2. Follow curiosity.

Always wanted to try pottery? Take the class. Want to learn Spanish? Join the group. You don’t need to go looking for friends—just go looking for joy. The right people often show up there.

3. Let it be awkward.

Yes, it might feel clunky at first. Introductions can feel vulnerable, especially when you’re not 25 anymore. But you’re not supposed to be polished—you’re supposed to be real. That’s how authentic friendships begin.

4. Don’t underestimate the power of one.

You don’t need a dozen new best friends. One meaningful connection can bring more joy than a crowd. Be open to the slow burn of friendship—it’s okay if it takes time.

Midlife is full of transitions. But you don’t have to go through them alone.

You’re allowed to want quiet and connection.
To enjoy your own company and crave a community that gets you.

This month, take one small step. Join the group. Say hello. Send the text.
You never know who else is hoping someone like you shows up.

Want more tools to build a life you love in midlife?

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THE MIDLIFE ROADMAP QUIZ

Not sure where to begin in midlife?
Take this 7 question quiz to discover your starting point.

Midlife can feel overwhelming - with shifting roles, changing relationships, and the physical and emotional changes that come with this season of life.

You might find yourself asking: 

  • Who am I now that my role has changed?
  • What do I want, and how do I create a life that feels meaningful?
  • Why do I feel stuck & disconnected, even though I've spent so much of my life giving to others?

Here's the good news:  Midlife doesn't have to be a crisis. 

Not sure where to begin? Let's find your starting point!

Take the Quiz!

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