I Swore I'd Never Do It Again. Then I Got Back on the Apps.

If you go back far enough in my old episodes, you'll hear me swear off dating apps completely. I hated them. I said I'd never do them again, probably more than once, and I fully meant it.

Then in June, I got back on one. And this whole summer happened because of it.

You Can Just Do Things

Lately I've been carrying around a mantra I picked up from some of the Gen Z founders I've met on LinkedIn: you can just do things. You have an idea, you put a plan together, you go do it. You want to talk to someone, you shoot your shot. You want to go somewhere, you go.

It sounds almost too simple to matter, and that's exactly why it works. Most of the reasons we don't do things are reasons we invented. The permission we're waiting on is permission we can hand ourselves.

Why I Got Back on Dating Apps in My 40s

Here's the part that makes me laugh. I'd told anyone who would listen that dating apps weren't for me. But we can change our minds. We all know that, and yet we treat our old declarations like they're carved in stone.

So I changed mine. I got back on an app and went in with a completely different mindset than I'd had before. Instead of bracing for it to be a waste of time, I decided to expect nothing except maybe meeting some cool people. Lovers, friends, relationships, who knew. That was the whole bar. Meet some interesting humans and see what happens.

That reframe is the entire reason the summer went the way it did.

The Words You Say to Yourself Matter

I'm a big believer that our words carry more weight than we give them credit for. Your subconscious doesn't know when you're kidding. Say something negative, even as a joke, and part of you files it away as an instruction.

So I've made a habit of watching what comes out of my mouth about my own life. Self-talk, money, everyday frustration, all of it. If I'd gotten back on the apps telling myself there'd be nobody worth meeting and it'd be a waste of time, that's exactly what I would have found. Instead I asked a different question: what could happen if I looked at this through a better lens?

Dating Apps Are a Full Contact Sport

Let me be honest about the reality, because a girlfriend recently told me she doesn't have the energy to get back out there, and I get it completely.

Dating on an app, if you actually want to date, is a full contact sport. I filtered through hundreds of profiles. Not an exaggeration, hundreds. I matched with maybe fifty people, had real conversations with maybe thirty, and went on dates with four.

And then there's the thing that will never not be strange to me: a man matches with you and does zero outreach. You liked a photo, he liked yours, you matched, and then nothing. I gave my number to six or seven men who never once reached out. Why ask for it? I genuinely don't know. That's the part of dating in midlife nobody warns you about, the sheer volume of effort that goes into getting to the handful of moments that are actually worth it.

I'd do all of it again.

What Dating in Midlife Actually Looks Like

Here's where it left me. I feel like a different version of myself than I was when I started back in June, and that alone makes the whole thing a win.

I've also been spending time with the same man I've mentioned the last couple of weeks. It's easy. It's comfortable. It feels mature, with no confusion and no games. We had a conversation early on about being completely honest with each other, no bullshit, and it turns out we're both just naturally that way.

He knows about the podcast, by the way, and hasn't listened to a single episode. I think that's intentional. He'd rather get to know me as this unfolds than get to know me through the show, and I love that.

And now I'm getting on a plane to Greece for a month. Someone's going to ask how that works when I just started seeing someone. It works because things happen the way they're meant to, and my suitcase is still in the closet, so I need to wrap this up.

Frequently Asked Questions

Is it worth getting back on dating apps in your 40s?

It can be, if you go in with the right expectations. Going back on the apps in midlife with a positive mindset and a low bar — meeting a few interesting people rather than hunting for a soulmate — takes the pressure off and makes the whole thing more enjoyable. The effort is real, but so is what you can find on the other side of it.

Why do men match on dating apps and never message?

There's no clean answer, and it's one of the strangest parts of app dating. Some men swipe on everyone, so a match doesn't actually mean interest. Others match, exchange numbers, and then never use them. It's not a reflection of you, so try not to read your worth into someone else's inaction.

How do you keep a positive mindset on dating apps?

Watch the way you talk about it, out loud and in your own head. If you tell yourself dating is a waste of time and no one worthwhile is out there, that's the experience you'll create. Going in expecting nothing except the chance to meet cool people takes the weight off every match and every date.

Can you change your mind about dating apps after swearing them off?

Absolutely, and there's nothing hypocritical about it. Changing your mind isn't going back on your word, it's letting new information and a new mindset move you. I swore off the apps for years and got back on with a completely different attitude, and it reshaped my whole summer.

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