I still have tons of old, dead conversations I've had on the app. This week I went back and reread the ones that went nowhere, some I ended on purpose, and some just sort of ended themselves. Horses, maple syrup urine disease, and a woman who compared a relationship to a newborn baby all show up.

See if you recognize yourself or someone you've talked to in any of these.

Five hundred conversations. Zero dates. Two weeks ago, I was ready to delete the app for good. Then something happened this week that made me stop and ask if I quit one week too early. I don't know how this ends yet, but here's what almost walking away taught me.

This isn't really about concerts.

It's about what people choose to put at the center of their identity, and what that secretly tells you about compatibility.

After decades in radio, playing in bands, working backstage, standing onstage, and watching live music from every possible angle, I've come to a conclusion that surprises almost everyone. It's also one of the fastest reasons I'll swipe left on a dating profile.

Why?

Because "I love live music" often isn't describing a hobby, it's revealing a mindset.

In this episode, I talk about Lollapalooza, dating profiles, getting older, nostalgia, identity, and why the things people proudly advertise about themselves aren't always the things they think they're communicating.

You may completely disagree with my conclusion. That's fine. The more interesting question is whether you're judging dating profiles by what people say, or by what those choices reveal.

If you've ever wondered what someone else's profile says about them, or what yours might be saying without you realizing it, this episode is for you.

Two calls in, before we'd even met, she told me something about her ex-husband that should've ended things on the spot. I almost let it slide anyway. Here's why I didn't, and what I've learned about believing people the first time.

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I share a building with 500+ people and can't remember the last time a stranger there turned into anything. Not a date, not a friend, not even a regular conversation. This week I figured out why, and it's not the building, it's not the city, it's not even really about being single. It's the same reason dating apps had to exist in the first place, and once you see it, you can't stop noticing it everywhere.

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My ex contacts me every three or four months. The message is always the same formula, she has something to tell me, but she never says what it is. This episode breaks down textbook avoidant behavior, why she vanished the last time I responded warmly, why she'll never acknowledge what ended us, and the uncomfortable part about why her three-month cycle is perfectly timed to the exact moment my memory finishes editing her back into someone worth answering. And yes, I'm calling it now. She'll be back in October.

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Politics has become one of the biggest filters in modern dating—but I don't think politics is actually the real issue.

Over the last year, I've noticed something changing on dating apps. People aren't just telling you what they believe anymore. They're telling you who they refuse to date before you even say hello.

So when did politics stop being something we discussed and start becoming part of our identity?

In this episode, I look at how curiosity, open-mindedness, echo chambers, and social media have changed the way we approach relationships. This isn't about picking a political side. It's about asking a much bigger question:

What happens to dating when we've already decided the other side has nothing worth hearing?

I'd love to hear your thoughts in the comments. Have you noticed the same thing on dating apps?

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A conversation that should have never happened made me realize something I hadn't connected before.

Dating apps and matchmaking services are trying to accomplish the same thing, but they're built on completely different incentives. One depends on engagement. The other depends on successful introductions. Once you notice that difference, it's hard to stop seeing it.

It's why so many people are giving up on the apps, and why I think we're getting close to the next evolution of online dating.

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I did sixty episodes of this podcast without ever showing my face. Then I turned on a camera and everything changed overnight. Comments, DMs, strangers feeling like they knew me — none of it happened for fourteen months and then all of it happened at once.

This episode is about why presence does something that photos and audio never can, what it means for your dating profile, and why the thirty seconds of video you haven't posted yet might be the only thing standing between you and a connection.

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I've finally had it. This one's a little different.

Shirtless showdowns, pickleball pansies, Wimbledon-level tennis jags on a public court, scooter shits, absurdly loud cars, and industrial-strength playground blunts.

Tune in for a completely reasonable and measured discussion. Obviously.

Video versions of the weekly podcast are always available on:

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