Happy Birthday to me.

Turning 60… and Starting Over

Tomorrow, I turn 60.

Even writing that feels surreal. Sixty used to sound like a number that belonged to “other people.” Not me. Not yet. And yet, here I am—on the edge of a new decade, with a cup of coffee in hand and a life that looks very different than I once imagined.

Two years ago, I found myself starting over after a divorce. Starting over at any age is hard—but starting over at this stage of life? It comes with its own quiet set of questions no one really prepares you for.

Who am I now?
What do I want?
And perhaps the most surprising question of all…
Do I really want to date again?

The answer, as it turns out, was yes.

But no one tells you how complicated, awkward, funny, and sometimes downright confusing dating over 60 can be. There are moments that make you laugh out loud, moments that make you question everything, and moments that quietly remind you that you’re still very much alive.

Over the past two years, I’ve had more first dates than I ever expected at this point in my life. Some have been lovely. Some have been… let’s just say, memorable for all the wrong reasons. And some have taught me things about myself I didn’t even know I needed to learn.

That’s really why I’m here.

This space—Dating with Della—is where I’m going to share those stories. The real ones. The awkward ones. The hopeful ones. The ones that happen when you’re rediscovering yourself while also trying to connect with someone new.

And yes… there will be coffee involved.

The name “Della” is special to me. It comes from my Aunt Dell—my mom’s aunt—who lived with us when I was growing up. She wasn’t just part of our household; she was part of our foundation. She taught us resilience without ever calling it that. She showed us grit, humor, and how to keep going, even when life didn’t unfold the way you expected.

She was also playful. Light. Full of life in a way that stayed with me.

As I step into this new chapter, I realize I’m carrying a little bit of her with me.

Because starting over isn’t just about loss—it’s also about rediscovery. It’s about realizing that there is still so much life ahead of you. That connection is still possible. That laughter still matters. That it’s never too late to open yourself up again.

So here I am.

Sixty.
Single.
A little wiser.
A little braver.
And still willing to see what happens next.

If you’re on a similar path—whether you’re newly single, cautiously curious, or fully immersed in the world of dating again—I hope you’ll find something here that feels familiar.

Like a conversation with a friend. Because that’s exactly what this is.

If you’ve ever found yourself starting over later in life, I’d love to hear your story too. We’re figuring this out together.

—Della