
You only have to be lucky once…
- Shannon Goertz
- Nov 14, 2025
- 5 min read
I’m in my late fifties, and I went on a first date recently. During our conversation, the woman started telling me about her most recent failed relationship. It was clear things hadn’t been going well between them.
Then she said — referring to what kept her in the relationship longer than she should have:
“You know when you do that thing where you just think maybe they’ll change eventually, or it’ll get better?”
I about spit my drink out and screeched:
“No, NOOOOOO! At this point in our lives, tell me — when has that ever actually worked out for us?”
Dating is ostensibly the business of searching for someone to love, but in order for it to go well, it requires us to first work on a much more fundamental relationship that we have with ourselves.
We won't be successful daters, or indeed successful lovers, if we haven't first reached a healthy perspective on our own natures.
(at this point you either possess introspection or you’re a professional victim)
Dating presents us with the ultimate test of our powers of discernment and of our sense of self-worth. So, what exactly does it mean to suggest that we may need to learn to love ourselves before we go on to try to love someone else? Merely that we won't be in any position to work out who is kind and good, who is worth investing in, until we are firmly on our own side.
We need to have overcome our self-suspicion to be sure of what we deserve, to have a healthy sense of our value in order to correctly judge who could adequately reward our presence, and in order not to despair at all the rejection we will inevitably encounter on our journey to love.
Here then are some of the many rules born out of adequate self-love that stand a chance of keeping us safe and more or less calm during the turbulence of the dating process.
1. If they take an age to answer a message, we must walk away.
2. If we feel obligated but deep down don't feel comfortable, we must walk away.
3. If they make us feel ashamed or scared, we must walk away.
4. If we need to keep reminding ourselves that they're right on paper but something in our depth stubbornly says no, we must walk away.
We must forever banish the idea that choice is limited. It is in its way infinite.
There will always be other people. The pool is constantly being refilled. The situation can change in an instant. We must wait as long as we need to.
We should spell out what we want clearly on. If they run away immediately, they would have done so eventually in any case, so we're merely saving ourselves time. We should try not to go off people who threaten to be nice to us, and we should strive not to fall in love at once with those who ignore us.
We should accept with grace that most people won't want us. We're really not for everyone, and we don't want most people either. This is going to be an exercise in a million perplexing ways in which one human can fall short of another's hopes. We aren't being willfully fussy.
We're interviewing for the most important job in our lives.
We're trying to stay true to a legitimately distinctive vision of happiness. We have no option but to be very difficult. And again……we only have to be lucky once.
We're trying to fill a single, very important chair, not a bus. If there's an ex in our background haunting us with a sense that it could have been much better with them, it evidently couldn't, or we wouldn't be here. So let's not compound our difficulties with nostalgia. Our exes became exes for solid reasons.
Don't be too jealous of the married and the settled. Life has a habit of eventually forcing everyone to take equal sips from the cup of sorrow.
Watch out in dating, as in relationships, for the so-called polite, people-pleasing, cowardly, shape-shifting ones, the ones whose disinterest wears a smile and who waste so much of our time with their dread of being rude or unkind. Some people are going to be plain unwell. Mental illness is a reality for a fair percentage of the population. We should be ready.
However auspicious a situation might appear, we must assume nothing too readily. We won't know for sure for a very long time. We must quash premature enthusiasm so as never to have to pay an undue price for it down the line. We must keep repeating, like a mantra, every time promised dawns, but we just can't tell yet.
Attraction matters. This isn't an unholy or cheap demand.
This is more than merely friendship. We should candidly register when the feeling is missing and move on without shame. We mustn't go to bed too soon. This creates obligations which is going to be exhausting to work our way out of. Let physical intimacy be the result of confidence in their emotional rightness, not an attempt to catalyze a bond. There's going to be plenty of time for all that later.
Take regular breaks. These auditions are terrifying. We're right to feel tearful and fed up. It's appalling to have to write and then delete so many scripts for our possible futures. It's sad to have to keep realizing how far we still are from “Home”.
Try to identify a concerned, kind friend, on whom to rely for counsel when perspective starts to slip and madness threatens.
We should notice more than we're usually encouraged to do whether or not they actually interest us.
Are their minds richly filled?
Do they make us feel cleverer than we feel on our own?
Do we want to know what they think?🤔
We might have to spend another 7,000 dinners with them. We should refuse all non-reciprocal situations. They're either keen on us, viscerally keen, or we must walk away.
We are never here to coax, beg, or drag the unwilling. We should be ready for numberless rejections and drain them of too much meaning. We mustn't turn them into referenda on our right to exist. They're about poor alignment, not about every loss we've ever had.
We must know that we could be alone, possibly forever, if we have to.
It's conclusively better to remain single until eternity than to give room to a compromise candidate. Solitude at least allows us, always, to maintain hope.
Finally, let it take as long as it has to. If we're still here this time next year, or the year after that, so be it.
Dating is an extremely demanding process. We're often going to feel close to surrender and folly. But the more we are on our side, the more we'll be able to hold in mind critical truth as we return home from yet another disappointing encounter.
We aren't in any way unlovable. We just haven't found the right love yet.
(99.9% of this content is from The School of Life and Alain de Botton, he is quite brilliant and you can find more of his content here www.theschooloflife.com)






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