If you're dating again after 40, maybe you know this one. You're on a third date, and something you noticed on the first one happens again. A sharp comment. A story where everyone else is to blame. You saw it, you let it slide, and now you're wondering how you got here.
I went 20 years before I was in a relationship again. Twenty years, trying everything in the dating playbook. Two things were part of turning that around, and Tom and I wrote both into Balding Overweight Sex Machine: a deliberate break from dating, and a short list called the Five and Five.
Why I stopped dating for a while
It sounds backwards for a man who wanted a partner, but I took a conscious break from dating. In the book we call it a dating moratorium. It isn't hiding at home. You still get out, talk to people, see your mates and try something new. What you stop doing is chasing: the apps, the endless messaging, going out with one goal in mind.
The point is to find out what it feels like to be detached from the outcome. That doesn't mean you stop caring. It means a date stops being a verdict on whether you're good enough. For me, the break gave me room to focus on myself and make small improvements every day, instead of chasing the next date to prove something.
In the book we suggest at least three months, with a mate checking in each week. I think it's worth holding that loosely. The length matters less than being honest about why you're taking the break, and what you'll build while you're on it.
The cake comes first
What you build is what we call the cake of a life: your home, your finances, your career, your interests and hobbies. A woman is the icing, not the cake. Icing's lovely, but eating only icing will make you sick. My recent articles have been about the cake: a tidy room, a fixed bedtime, a gym bag packed the night before. A break from dating gives that work some room.
My Five and Five, as it stands today
The second tool is a list: five must-haves in a partner, and five deal-breakers. Here's mine right now.
Must-haves
Emotional intelligence
A sense of humour
Playfulness
Kindness
Looks after their health: eats well, stays active
Deal-breakers
Very critical
Constant complaining
Victim mentality, never taking responsibility
Rude to restaurant staff
You'll notice that's four deal-breakers, not five. That's fine. The list is still being tested.
If you've read the book, it isn't the list I wrote there. Back then I had intelligent, nice to look at and independent, and lying and being a dream-killer were deal-breakers. Kindness, humour, being critical and a victim mentality carried over. The rest moved. That's not me getting it wrong the first time. That's the list doing its job.
Deal-breakers are warning signs, not a battle
The deal-breakers are just warning signs. You're not there to argue with them or fix them. You spot them, and you politely decline. Thank you, but no thank you.
That's why I like rude to restaurant staff. You can see it on a first date over a coffee (in the book we say a first date doesn't need to be anything dearer). I think how someone speaks to the person bringing the coffee tells you a fair bit about how they'll speak to you once the polite phase wears off.
Here's the Nice Guy trap. We see the warning sign and stay anyway, hoping we can be nice enough to change it. Then it builds, and we blow up later. Declining early is kinder for both people.
The must-haves are where your focus goes
The must-haves are where I put my attention. Writing them down isn't about getting them right. It gives you a lens, and a constant reminder. You're not ticking boxes on a clipboard. You're noticing. Can she laugh when something goes wrong? Is she kind when it costs her something? Does she look after herself?
With Sam, the connection grew during COVID, through shared experience rather than any plan. I remember noticing how she handled something difficult, how it clearly affected her, and how she came back the next day to support someone else going through the same thing. You won't find that on a dating profile. You only see it when you're paying attention to how someone actually lives.
The harder question
And that's the catch. Writing the list is the easy part. The harder question is whether you're the man who deserves those qualities. Do you embody them yourself?
My own list points straight back at me. Looks after their health? Then I'd better be looking after mine, and that's what the bedtime and the packed gym bag are about. Humour and playfulness? Then I need to bring some lightness myself. As we put it in the book, you can have preferences in dating, but you must also be worthy of them.
That's what the break is really for. It isn't time off. It's time to become the man on the other side of your own list.
Write your own Five and Five (about 20 minutes)
Brain-dump first. Write everything you want in a partner and everything you can't live with. Then weigh them up and cut each side to five, or fewer if that's honest.
Make each must-have visible. Next to each, write what it looks like on an ordinary day.
Give each deal-breaker an early sign and a polite exit. Keep it simple: thank you, but no thank you.
Turn it around. Next to each must-have, write an honest note on whether you live it yourself, and one thing you'll do this month to show it.
Put it where you'll see it, whether that's your phone or the inside of a wardrobe door.
Test it. Come back in a month and change what doesn't hold up.
Thinking about a break from dating too? Decide how long you'll give it, and who you'll check in with.
At the end of the month, ask yourself: what did my list help me notice that I'd have let slide before?
My book
The Five and Five, the dating moratorium and the cake of a life are all in Balding Overweight Sex Machine, the book Tom and I wrote. Have a look if you're dating again and want the full version.
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This is my experience, not therapy or psychological advice. If any of it brings up something heavy, please talk to a qualified professional.