Getting married was nice. There, I said it. It was nice to have a partner, to build something with someone who wasn’t just passing through. It wasn’t fireworks, it wasn’t some burning, all-consuming passion, but it was a partnership—goal-oriented, pragmatic, two people moving in the same direction. And for a while, that was enough.
But it wasn’t love. Not the kind they write songs about. Not the kind that turns you into a madman, clawing at your own skin just to feel closer to the other person. No, it was two people agreeing to go through life together, like business partners shaking hands over a deal.
And then the deal fell apart.
When I got divorced, I owned a tequila bar called Amalia’s. One day, I was a husband, a man with a family, a foundation, a purpose. The next, I was a walking neon sign that said Free Booze and Poor Impulse Control. Announcing my divorce was like throwing chum into shark-infested waters. Women I’d never spoken to suddenly wanted to know me, really know me. It wasn’t about me. It was about what I represented—the bar owner, the man with a million dollars, the guy who was fun, who could buy drinks, who could take them places.
It was all so transparent. But I played along. What else was I going to do? Sit at home and contemplate the wreckage of my life?
And then I watched my friend go through the same thing. He got caught cheating. Didn’t know why he did it. Didn’t understand what he was missing or what he even wanted. His marriage crashed and burned, and within a year, he was remarried. A fucking year. No reflection, no pause, no moment to even consider what the hell had just happened. Just rinse and repeat.
And that’s what most people do. They fill the void with another person. They replace one warm body with another, as if swapping out a dead lightbulb. They don’t stop to think. They don’t stop to feel. Because feeling hurts.
Meanwhile, I was out in Bend, Oregon, living like a goddamn Roman emperor. My place was a revolving door—nine different people in and out in a single day, not one of them staying the night. Married men would pull me aside, hungry for the details, treating me like some kind of sage. Tell me, oh wise and promiscuous one, how do you do it?
Easy. I had money. I was fun. I was good in bed. And I didn’t give a fuck.
I never wanted to be attached. Even back in high school, I was like this. Before I got married, I was like this. And now, post-divorce, I was the slipperiest bastard you’d ever meet. I dated someone for three years and then ghosted her overnight to move back to the mainland. The second someone started using words like we, I started planning my escape.
What are we doing this weekend?
Nothing. I’m doing nothing. You can do whatever the fuck you want.
What are we having for dinner?
I don’t know. You’re blocking the fridge.
Let’s go on vacation together.
I just heard the word together, and now I want to die.
That’s the thing about freedom—it comes at a cost. At first, it’s exhilarating. No obligations. No compromises. No dragging yourself to a kid’s birthday party for a child who isn’t yours, pretending to care. No going to Disneyland for the tenth goddamn time. No negotiating which in-laws’ house you have to suffer through on Thanksgiving.
It’s beautiful.
And then, slowly, it’s not.
Because the thing about being completely untethered is that you start to float. You drift. Days blur into each other. One nameless woman becomes another. One barstool turns into another barstool. You start measuring your life in empty glasses and short conversations.
And then you get older.
And suddenly, you understand.
You understand why your father stayed in a loveless marriage for 35 years. You understand why your uncle tolerated your aunt’s bullshit until the day he died. You understand why all those smiling couples on Facebook, pretending to be so goddamn happy, are really just clinging to each other out of necessity, out of fear.
Because the alternative is this.
Freedom is a seductive thing, but it has sharp edges. At first, you mourn not seeing your kids every day. Then time dulls that pain. Then you realize you don’t actually belong to anyone anymore—not in a deep, meaningful way. There’s no partner to say You did good today. No one to push you, to cheer for you, to hold you up when the weight gets too heavy.
I’ve lived without structure for so long that I’ve forgotten what it’s like to build. And men like me—we need goals. We need to be chasing something. We need milestones and finish lines and the occasional goddamn parade when we cross one. But without a partner, what’s the goal? Who am I proving anything to? Who do I share the victories with?
I’m 55 now. How many weekends do I even have left? How many sunsets? How many full moons? I used to count women. Now I count time.
Do I cash in my freedom for something deeper before it’s too late? Do I let someone in, knowing they come with their own baggage, their own bullshit, their own needs that will inevitably clash with mine?
Or do I keep floating?
Do I keep drifting from port to port, the way my grandfather always said I should?
Because eventually, you have to ask yourself—how do you know when you’ve reached your last port?
How do you know when it’s time to drop anchor?
