Episodes

The profiles have gotten worse. Not slightly, significantly. The Instagram handle in the serious relationship bio. The wrong age that somehow always gets entered younger. The AI bio with the em dashes in it. The skyline that doesn't exist. The woman who liked you first and spent the conversation taking shots at you. This episode is about what all of it actually signals, because someone is always paying attention, even when you think they're not.

In this episode, I share the conversation that almost never happened: a rematch with a clear political filter that put me in the ‘no’ category. She pushed past it anyway, and what unfolded forced me to confront my own label-based shortcuts, like the flight attendant rule and almost swiping left on someone 20 miles away in Chicago’s brutal traffic. We explore the difference between healthy behavior filters and dangerous assumptions, the invisible cost of missed connections, and how to ask better ...

You're still on the apps. Still swiping and responding. But something shifted and you know it. The curiosity and patience is gone. You're dismissing people in thirty seconds over things that don't mean anything, and calling it standards. It's burnout. And the problem with staying on the apps when you're already this depleted is that something good could show up right now and you probably wouldn't recognize it.

Being alone can feel peaceful, until something reminds you what connection actually feels like. This episode explores the difference between being okay alone and getting used to it.

Episode 50. One year. I didn't think this show would make it this far. Today I'm not teaching anything or making a case for a position, I'm just talking to you directly. What solo podcasting actually costs, what I got wrong, what kept me going, and where things honestly stand.

Most people assume the rules protect them. Until the day they realize rules only matter when someone has the power to enforce them. This episode is about the moment you realize the world doesn’t operate the way you were told it does.

"I’m not ready” sounds mature, responsible, and self-aware. But what if it’s just a softer way of saying no? In this episode, I unpack what readiness actually means, when waiting is wise, when it’s avoidance, and why nobody ever reaches a point of being fully healed before love.

Ask anyone why their last relationship ended and you’ll hear a very confident story. The problem is, most of those stories aren’t accurate. This episode breaks down how and why breakups get rewritten over time, why nobody thinks they were the problem, and how that mindset will completely wreck future relationships.

Most second dates are lost long before the conversation even matters. In this episode, we’re talking about the small, brutally simple things people notice instantly... hygiene, presentation, manners, effort, and why skipping them silently kills attraction before you ever get a real chance. Nobody tells you this stuff. They just ghost you. So let’s talk about it.

Dating apps didn't stop working because you got older, they stopped working because they were redesigned not to work. The apps realized their most profitable users are the ones who never succeed. This episode breaks down how dating apps shifted from helping you find someone to keeping you just hopeful enough to stay, why the pool is now full of the emotionally unavailable, and why you keep blaming yourself for a system that was never designed for you to win.

When you start dating someone who is emotionally available, it can feel…off. There’s no anxiety, no guessing, and no emotional rollercoaster. They text you back, show up, and don’t disappear. And somehow that can feel less exciting than someone who’s inconsistent, grieving, or still emotionally attached to their past. In this episode, we break down why emotionally healthy people often don't feel as exhilarating at first, why emotionally unavailable people feel magnetic, and how your nervous s...

The psychology behind why dating feels worst on Sunday nights, why you miss your ex when you’re tired, and how emotional exhaustion makes your brain lie about your future.

Americans think dating is hard everywhere. It's not. The way we do it, app-driven, hyper-individualistic, like a never-ending job interview, is an outlier. This episode compares how dating works in France, Japan, and Denmark, then breaks down what Americans are getting wrong and what we can learn from cultures that make connection less exhausting and more human.

Going back to an ex feels like skipping the line. You already know each other, you have history, and starting over sounds exhausting. But research shows that on-again, off-again relationships usually increase stress, conflict, and dissatisfaction. This episode breaks down when a second chance can work, and when you're just yearning the familiar past.

In the Season 3 opener, we're going to upset some listeners as we discuss how, when someone says they’re “still friends” with their ex, it often means the relationship never fully ended. We explore emotional proximity, unfinished attachment, and why staying close to an ex quietly sabotages new relationships, even if no one wants to admit it.

Single on New Year’s Eve and spiraling? This episode is a reset. Trent talks about what’s really going on behind those perfect couple posts, shares his experience staying way too long in an abusive relationship, and explains why being alone that night might actually be the win. You’ll get a list of “don’ts” for the night, a few better options, and a different way to think about going into 2026.

There’s a point where dating apps stop feeling hopeful and start feeling heavy. In this episode, Trent talks about dating while tired. When you still want connection, but don’t have the energy to keep auditioning for one. From app burnout and inbox math to why effort no longer scales the way it used to, this episode is about protecting your energy without giving up on love entirely. If you’ve ever seen a “someone liked you” notification and felt absolutely nothing, you’re not alone.

Resetting your profile sounds like a hack. Sometimes it’s just replaying the same disappointment. Here’s what the algorithm is doing, when resets help, when they tank you, and the real strategy that gets you seen.

This episode breaks down why the dating pool feels smaller than ever, what happens when you have to be better than someone's already good life, and how to handle age gap relationships. Plus, a listener question about dating younger women.

This week, we're getting deep into why good people can’t focus on one person, and how choice overload means you’re always one swipe away from being replaced. It's not something you're going to want to miss.

Ever wonder why we only recognize the best moments after they’ve slipped by? This episode dives into the ache of missing wonderful chapters, even as you’re living them. From leaving behind messy apartments and old relationships to the science of nostalgia, regret, and derealization. It’s all about why we struggle to notice the good stuff when it’s right in front of us, and how to start being present before it’s too late.

How do you see yourself, and how do others see you? One summer, everything changed for me on the outside. On the inside? Not so much. This episode explores why we never really feel like we fit, even when the world says we do. If you’ve ever felt like you’re faking it, this one’s for you.

I’ve been living in a hotel with my dog, Holly. Not on vacation, but stuck between homes, routines, and tourists in the elevator. This week, I discuss holding it together when nothing feels familiar while pretending everything is fine on the air. I’m also realizing that "boring" might have been the best phase all along.

A quick detour before the next full episode drops. These are the moments listeners keep messaging me about. The parts where I apparently said something honest enough that it stuck. If you’re new, this is a good place to start. If you’ve been here since the beginning, thanks for staying.