Dating Again in Midlife: The Summer I Decided to Say Yes

I matched with a guy on a dating app. We planned a date. Thirty minutes later, he unmatched me.

That's how I'm opening The Summer of George.

I named it after the Seinfeld episode where George gets let go from his job, ends up with a three-month severance, and proclaims it The Summer of George. That's me right now. Not unemployed, but standing in a quiet moment after four very busy months, looking around my house in Scottsdale, and deciding to do something about it.

Why I Got Back on a Dating App in Midlife

I said I would never get back on a dating app. I told anyone who would listen that the apps stressed me out and didn't give me anything worth the energy.

And then I got back on one anyway.

Here's what changed. I decided that if I didn't get back into the energy of putting myself out there, I never would. Dating is energy. When you're not in it, you're not inviting anyone in, you're not opening any doors, you're just at home.

I went in with a different mindset this time. I'm confident in who I am. I know what I'm looking for. And I'm not going into every meetup like it's an audition for the rest of my life. Going into a first meeting wondering if this is your forever person is crazy town. It's an interview at best. Are you the same person I saw in those little boxes on my screen? Do you look like your photos? Is your voice what I expected? That's the whole first meeting. Everything else comes after.

How a New City Quietly Stopped Being a New City

I moved to Arizona because people love to visit Arizona. The trade-off, which I did not fully clock until recently, is that your social life ends up running on other people's calendars.

For about four and a half months, my calendar was full. Friends, family, people I hadn't seen in years. Conferences, retreats, vacations. It was amazing. I learned more about Scottsdale than I ever expected to, tried a ton of new restaurants, felt connected.

Then it ended. The snowbirds left. The heat came in. The visits stopped. And I had to be honest with myself: I had not done a very good job of building a life here that belonged to me. I networked a little. I made a couple of friends, who I love, but who are all in completely different phases of their lives than I am.

It got quiet.

That's the thing nobody warns you about when you move to a new city as a single woman in midlife. The honeymoon period is real and it ends. And when it ends, you find out whether you actually built a life or just borrowed one from everyone passing through.

What Saying Yes Actually Looks Like

Saying yes is the underlying current of the Summer of George.

In practice that means workout classes. The ones I've been meaning to try and kept skipping. They're also a great way to meet people, because everyone is doing the same thing at the same time and you have an automatic conversation starter the moment it's over.

Networking. Actually showing up to things, not just scrolling past them. I built more open time into my summer so I could say yes to invitations without the calendar fighting me.

A dating app. Yes, I'm on one. I said I wouldn't be. I am.

And the broader practice: when a friend invites me to do something, I'm saying yes. When there's a women's meetup, I'm going. When someone says yoga in the park, I'm there. The point is not that any one of those things is going to change my life. The point is that being the woman who says yes is a different woman than the one who says she'll think about it.

Dating When You're Google-able

Here's something I didn't think about when I started the podcast.

I didn't think about the fact that I'm single. I didn't think about the fact that I'm Google-able. And I didn't think about the fact that someone could match with me, want to take me out, and then Google me and decide to bail before we ever met.

That might be exactly what happened last weekend. I matched with a guy. We made plans. Thirty minutes later, I opened the app and watched my matches count drop. He had unmatched me. I went into an incognito window and tried to figure out what he could have searched. I came up empty. But the point isn't whether he Googled me this time. The point is that someone will. Eventually someone will sit across from me, ask about the podcast, hear what it is, and decide that's not what they want.

That's fine.

The person I end up with is going to love this version of me so much that my past becomes part of the reason. Because of it, not in spite of it. So if a man bails before the first date because he doesn't like what he finds on Google, he has saved us both time. I don't have a redemption arc to sell anyone. I'm not softening anything. The right person is going to be interested in the woman this past made.

The Loneliness Most Single Women Don't Talk About

I want to name something most single women in midlife do not say out loud.

I love my life. I wake up grateful. I look at the home I built for myself, the work I get to do, the way I get to interact with so many of you, and I think, I am the luckiest woman on the planet. That is real.

And I'm still lonely sometimes.

Both of those things are true at the same time. Pretending only one of them is true is how a lot of women end up in relationships that don't serve them. We meet someone who isn't great, but the silence is real, and the silence wins. We settle, because settling looks like company. We stay too long, because leaving means going home to ourselves.

I am not settling. I am not waiting for the wrong person to show up just because something is better than nothing. The Summer of George is the opposite of that. It's me practicing the muscle of choosing my life on purpose, even when it's quiet, even when no one is visiting, even when the app is the only thing that has my attention.

What This Means for the Podcast

The regular Thursday episodes continue. Guests, solo episodes, all of it stays on schedule.

What's new is a weekly bonus episode through September 30. Less polished, less produced, filmed wherever I am that week. Scottsdale, LA, back to Scottsdale, Greece. The point is to bring you along in real time.

The Summer of George runs June 10 through September 30. If you want to come along, come along.

FAQ

Should single women in midlife get back on dating apps?

There isn't a universal answer, but the apps work best when you're not depending on them. If you're going in for fun, for practice, and for the energy of putting yourself back out there, they can be useful. If you're going in desperate for a partner, the apps tend to make that harder, not easier.

How do you make friends in a new city as an adult?

By going to the same places more than once. Workout classes, recurring meetups, neighborhood spots. Repetition turns strangers into faces you recognize, and faces you recognize into people you talk to. Most adults treat friendship like it should happen accidentally. It doesn't. You have to keep showing up.

What does saying yes more actually mean as a single woman?

It means defaulting to yes on invitations, social opportunities, and experiences that feel slightly outside your comfort zone, especially when you're tempted to skip them. The goal isn't to say yes to everything. The goal is to interrupt the habit of saying no to things just because they're inconvenient.

Is it normal to feel lonely in midlife even when your life is good?

Yes. Loneliness isn't a verdict on your life. It's a signal that you're a human being who wants real connection. Plenty of women with full, beautiful lives still feel lonely, especially after moving to a new city, getting divorced, or starting over. Naming it is the first step. Building toward it is the second.

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