WHEN YOU'RE LOVING
18. How Do I Know This Is the One?
"There is no remedy for love but to love more." —Henry David Thoreau
Dear Kids,
I want to be honest with you about something before I go any further: I am not the person who has earned the right to answer this question with authority. I have not "succeeded" at love in the way that would let me speak from the other side of it. Everything below is one analytical person's attempt to think clearly about something that resists clear thinking, and you should take it with a healthy grain of salt. But I'm a believer in learning from other people's mistakes so you don't have to repeat them, and I've made plenty. So here's your chance to learn from mine.
I know what you're probably thinking — those four criteria I wrote about a few letters back sound like brutally tough standards. How do I know the person I'm dating is "the one"? What if they're a psychopath who happens to be charming for the first fourteen dates? Or the gentler version of the same fear: I'm dating someone I genuinely like — but how do I know they're the one? What if someone better walks into my life tomorrow?
When you ask old married couples, the most common answer is some version of "you just know when you know," or "I fell in love at first sight." Which is deeply unhelpful — and a little cruel — to the single person, because it invites the question, "Then why am I so unlovable?" or "Why am I only lovable to psychopaths?" You look at them, with their adorable family and their cute grandkids, and through your tears you wonder whether this is just hindsight bias, or some benevolent Stockholm Syndrome they've told themselves into.
The honest truth is: you'll probably never know whether this is the perfect person for you, because it's impossible to consider the counterfactual — all the paths and partners you might otherwise have had. But I'm an analytical person by training, and "you just know" doesn't help me, and probably won't help you either. So I went looking for something more concrete. And it turns out there is actually a branch of mathematics that gets surprisingly close to the dating question.
The Secretary Problem, written on a napkin
It's called the Secretary Problem, or the Explore/Exploit problem. The setup goes like this: you have to interview n candidates for a position, one at a time. After each one you must either hire them on the spot or pass — and if you pass, you can never go back to them. (Sounds a lot like dating, doesn't it — except a lot of people do try to go back to their exes, which is generally not advisable.)
I won't drag you through the proof, but the optimal solution comes out beautifully clean: reject the first n/e candidates outright — roughly the first 37% — and then choose the next candidate who is better than everyone you've seen so far. For n = 100, you'd reject the first 37 people, then pick the next one who beats them all. It doesn't guarantee you find the best candidate. But of all possible strategies, it gives you the highest probability of doing so.
I remember the first time I actually sat down and did this math for myself. It was on the back of a napkin, late at night, somewhere between heartbreak and clarity — exactly the wrong and the right time to be drawing decision diagrams about your love life. But once you see it, you can't unsee it.
You're not going to date 100 people, of course. So you have to translate the formula into something usable. Say you date roughly from 17 to 31, with an average relationship lasting two years — call it about 7.5 serious relationships in that window. The optimal strategy then says: reject (in the marriage sense, not the "don't be friends" sense) the first three relationships, and then choose the next one who is better than all of those.
I'm aware how cold that sounds when written down. The math doesn't care about your feelings. But the math is also less cynical than it looks — what it's really saying is that you should treat the first few relationships as a learning sample, not a final answer. That's a generous read.
There are three things I want you to take from that napkin.
1. Your first relationship probably isn't The One — nor your second, nor your third.
This makes intuitive sense even without the math. Early on, you're discovering what's out there — learning who the candidates are and what they offer, and just as importantly, learning who you are. For all of society's glorification of teenage love and high school sweethearts, I think it's irrational, even irresponsible, to decide your life partner on the first try. It's like letting your 15-year-old self pick your haircut and your fashion sense for the rest of your life. You can grow the bangs back after a Britney moment — but you can never get back the time.
And dating is actually harder than the Secretary Problem, because it's multivariate. Not only are your potential partners' traits changing — your own internal criteria are evolving too. Move to a new city and the entire candidate pool changes. Change careers and what you value in a partner changes with you. All of this argues for a larger sample size before you commit. When I think back to who I was a decade ago, and what I wanted from a relationship then, there is no chance those wants are the same today. Yes — some couples are lucky enough to meet at 15 and stay together for a century. Statistically, that probably isn't you. And honestly, if it is you, you don't need this letter.
2. The better way to find The One is to widen your window.
Mathematically, you can improve your odds in two ways.
Widen your dating window — give yourself a longer runway to meet and learn from more people. Geography matters here, too: in a medieval village in the 1300s your candidate pool was a few dozen souls; today the whole world is open to you, if you let it be. Travel. Move. Take the job in a different city for a year. The pool is wider than your current zip code.
And move on when it isn't working — if you can honestly decide within a year that something is wrong and leave, rather than languishing in a bad relationship for three, you free yourself to keep searching. This is the one I find hardest, kids. I have wasted years politely refusing to see what was already obvious.
Of course, the paradox of choice is real — too many options can paralyze you, and at some point you do have to choose someone and bet on a shared future, knowing neither of you can fully predict how you'll change. But I know with certainty that making that choice at 17, with the emotional maturity of a monkey, would have been wrong for me. A decade later, a little wiser and a little steadier, I can at least make a slightly better one. Same monkey, marginally better at picking.
There's a passage I keep coming back to from Chip and Dan Heath's Decisive, which I read during a stretch where I was overthinking a decision that wasn't even mine to make yet. Their argument is that most of us frame our biggest choices as binary — should I marry this person, yes or no? — when the better question is almost always wider: what am I actually trying to build, and which of the available paths gets me closer to it? The reframing sounds small. It isn't. The "Is this The One?" question is unanswerable, because the counterfactual doesn't exist. The "What life am I trying to build, and is this person someone I want to build it with?" question is answerable, slowly, by paying attention. The Heaths gave me language for something I'd been groping toward on that napkin: the math gets you to a threshold, but the right question gets you across it.
3. Once you've chosen — the lessons that actually make love last
The math gets you to the threshold. It does not get you through the marriage. So here is what I've actually learned about love itself, from making a great many mistakes and still struggling, daily, to follow my own advice.
It's going to be messy — do it anyway. There's no such thing as a perfect relationship, because there's no such thing as a perfect person; we are all flawed creatures. And that's a good thing. The irrational sacrifices you make for someone, the passionate outbursts of feeling — aren't those the very core of romance? A relationship without them would be boring. Accept that the first few attempts will be dumpster fires. That's not failure; that's the curriculum. You learn who you are, you recover from heartbreak, and you become a better person in the process.
Know who you are, and hold to your core values. It's easy to feel you should be in a relationship simply because everyone else is — and in that rush, to let your standards slide and compromise on what matters. Don't. Learn the difference between feeling lonely and being alone. Be comfortable with yourself first. A healthy relationship is not a crutch for your insecurities, nor a project for healing someone else's. It's the same lesson I keep returning to in these letters — you can't choose authentically for someone else if you haven't done it yet for yourself.
Don't be afraid to shoot your shot. The cute person sitting alone at the bar is probably there for a reason — go find out what it is. The embarrassment of rejection is temporary; the regret of never knowing whether they could have been your future spouse lasts forever. (Although — a bar at 3 a.m. is not the ideal place to meet a future spouse. Try pickleball, or a meditation retreat, or a friend's wedding.) It sounds easy in principle, and we all struggle with it in practice. The cure is probably just to get rejected enough times that your ego stops being so fragile. Mine is still working on it.
Don't get trapped by the sunk cost fallacy. Your time is limited — don't waste it stuck in something you already know won't work. Have the hard conversation instead of avoiding the sensitive topic. You'll save your time and your partner's, and you'll both be grateful in the long run. The opposite error exists too — giving up too easily, or fleeing every relationship at the first whiff of friction — but in my observation, people far more often drag relationships on past their natural end than cut them short.
"Don't be reckless with other people's hearts. Don't put up with people who are reckless with yours." Those are lyrics from one of my favorite videos on the internet — a philosophical life-advice masterpiece nominally about sunscreen. Have the compassion to let people go, so you can both begin a better path.
The best way to find someone is to become the best version of yourself. The law of attraction holds here: you attract what you put out. Want someone healthy and active? Become healthy and active. Don't be surprised that it's hard to meet someone with good habits when you're spending your nights at the bar. This extends to your friendships, too — often the best way to meet the right kind of person is simply to be surrounded by the right kind of people. And in the end, that may be the truest path of all, because it's naturally aligned with who you already are. The Secretary Problem assumes the candidates are a fixed pool. They aren't. You're a candidate too. The pool you attract is downstream of who you become.
I can't tell you, finally, whether the person across the table is The One — no formula can. The napkin math gets you to the threshold; it does not walk you through the door. But I can tell you that if you've widened your window, held your standards, and become someone genuinely worth choosing, the odds are as good as a father could hope for you. The rest is courage, and time.
And the rest, when it doesn't work out — when timing or geography or the wrong year of life keep two right people apart — well, that's the next letter.
Love,
Dad.