The Checklist I Burned to Find My Wife
I had a list.
Estonian. Debt-free. Family not certifiably insane. Grit, faith, an athlete with a strong mindset.
I carried that list around for the better part of a decade, like a man carrying a treasure map to a mountain that didn't exist.
Then I fell in love with a girl from Long Island who checked half of it, and I've never been so grateful to be wrong.
That's the whole essay, really. Everything else … how I got there.
…
Lifestyle design, the business of doing the big things right so the small things fall in line behind them, has a foundational decision most people never put on the list: who you marry.
I read once, in a book about the longest-lived people on earth, that this single choice compounds everything after it.
Get it wrong, and you spend the rest of your life paying it down. Get it right, and the interest just keeps rolling in.
I'm no expert on love, or on women, or frankly on much of anything. But I did enough of the big things right that I ended up married to my best friend. None of what follows is a formula … I'm just telling you what I did, in case a morsel of it resonates.
The Monk Years
I didn't date in middle school or high school, and barely in college.
A couple of short, doomed relationships, both of which I ended myself, not because anything was wrong with them but because I wasn't done building whatever it was I thought I was building.
People noticed. My grandmother wanted to know what was wrong with me. The open-minded new grads wanted to know, gently, delicately, as if handling a bomb, whether I was gay or maybe asexual.
I was neither. While I may have given a convincing performance of a man struggling to pop the closet door open, I was (and still am, by choice) a straighty.
What I actually was, was terrified. Of commitment. Of an accidental pregnancy. Of getting permanently welded to someone over one reckless night. Of burning years of my life on a person who wasn't the one.
So for a couple of years after college, I opted out entirely. Not a vow of celibacy. Just a very long, very cautious flinch that happened to look exactly like ... a vow of celibacy.
I spent that time trying to live like a man in a hurry to have lived.
I ran a marathon. I summited mountains. I self-published ebooks nobody read. I practiced Estonian and guitar. I sat still and meditated, I crushed podcasts, said yes to the occasional psychedelic (in the name of research) and travelled solo to places I’d barely read into.
I wanted to arrive at a relationship already having lived, so I wouldn't spend it wondering what I'd missed, or worse, quietly blaming her for the missing.
I also had a job I didn't love and zero intention of keeping. Committing to someone, I figured, meant committing to that life too, so I held everything loosely …
Friendships. Plans. Zip codes. I was a “minimalist”, and not just about furniture. Mobility was the whole religion, and I was its most devout, mildly insufferable convert.
I'd grow out of it eventually, and living at that extreme set me up nicely for the next one.
The Checklist Years
As I got older and, mercifully, less socially useless, I started actually wanting connection instead of fleeing it.
A little serial dating. One four-month long-distance relationship. And somewhere in there, a list crystallized. The one I mentioned at the top.
Estonian heritage. Shared family values. Faith, grit, sports, self-respect, no debt, no family drama. I was hunting Ms. Perfect with the precision of a man assembling furniture from instructions he'd written himself, and I couldn't figure out why nothing ever fit.
The list finally cracked, appropriately, in Estonia. I was talking to a girl about my age, and I mentioned my whole imaginary-heritage-bride plan. She just looked at me. "How are you going to meet an Estonian over there? Why don't you just come to Estonia?" Duh.
That fall, I took a job in Estonia. And in the very same season, doing absolutely nothing to honor my own checklist, I started dating an American girl from Long Island.
The Girl Who Broke the List
The first date was unlike anything before it. I knew it, and I still didn't trust it.
Old habits.
I told her I was moving overseas for work, half-expecting that to be the end of it. She said, "So what, we'll figure it out. Let's give it a shot."
She said it lightly, like it cost her nothing. It cost her plenty. She just didn't let me see it for years.
I lived overseas. COVID hit. We reunited after months apart, moved into other people's spare rooms for over a year, then landed in Texas.
Lockdown had broken something in me. I'd lost trust in people and lost that glimmer for life. And me being me, I did what any emotionally stunted man raised on self-help podcasts would do: I blamed the relationship instead of the global pandemic. Seemed easier to fix one girlfriend than fix the entire world.
More than once I daydreamed about retreating to my old workshop of solitude and self-improvement. Just me, a journal, and zero witnesses to my personality.
Thank God I didn't. Turns out the cure for "everything feels broken" isn't more alone time. I'd already run that experiment for two years and the results were ... mixed.
It wasn't until Texas that I could finally see what we had, clearly, in the daylight.
Three years after that first date, I proposed. Back in Estonia, fittingly … the homeland I'd once thought I needed to import a wife from, now the place I locked in the one I would marry.
She'd put up with a stubborn bronco for three years. She'd more than earned it.
What the List Was Actually For
Somewhere in all this, and this was before I met my wife, mind you, not some retrospective spin I'm putting on it now … I also learned to value connection in general, not just the romantic kind.
I once lived like a hermit in Montana, fully committed to the solitary-writer life, and fully miserable in it, which taught me something useful: turns out man cannot live on prose alone.
I moved back east, took up jiu-jitsu, read Dale Carnegie unironically, and forced myself, badly at first, like a man learning to swim by drowning politely, to get curious about other people instead of just enduring them.
It took years before it stopped feeling like a performance. But it's the reason I was able to recognize the real thing when it finally walked into the room.
If you're staring down this decision yourself, whether the person you're with is the one or you haven't met them yet … your list will look nothing like mine, and that's fine. The list was never really the point.
Here's what was: I met my wife, after years of "self work", right when I'd basically given up. I was serial dating my way toward a move to Estonia with all the romance of a man filing expense reports.
And that, it turns out, was the secret. The stakes were low, so I stopped auditioning for marriage and started just paying attention. My whole system had two settings. Big red flag, or a flat "eh, this ain't it"? Move on, don't look back. Nothing wrong, decent time, mild spark? Go on another date. That was the entire formula.
I dated some good women along the way. Some attractive. Some more friend than life partner material. Until ... I found the one who was, inconveniently for this metaphor, both.
Because here's the part nobody tells you: American culture sells you love as fireworks. Eyes meet across a bar, sparks fly, fireworks in the sheets by date three, roll credits.
That's not love though, that's a match head.
Real love is a woodstove, not a firework. It won't dazzle you in the first five minutes, but it'll keep you warm for forty years if you feed it right ... and even then, the fire simmers down sometimes.
You will have doubts. You'll both mess it up, more than once. You'll consider walking away, and at 2 a.m. your differences will feel completely irreconcilable.
That's not a sign you picked wrong. That's just the sine wave doing its work. Ride out the peaks and troughs, and calm waters lie ahead. Where the real stuff happens.
Coffee in silence. A hand on your shoulder after a hard week. Doing absolutely nothing together on a rainy Sunday, and somehow it's one of the best parts of the week. Not to mention all the adventures still ahead, ie. what I used to do solo, I now do with a partner (and a budding family).
F*ck fireworks. Marriage takes work.
Hold the list loosely, because the right person has an ugly habit of showing up right when you've stopped checking boxes and started looking somewhere else entirely.
Mine did. She didn't speak a lick of Estonian either, but she's learning. And so am I.
Love isn't a checklist, it's a practice.