Wedding planning is somewhere around 400 decisions, most of them about one single day. Marriage is more like 40,000, spread over decades, and I promise you none of the napkin ones will matter by your first Christmas.
My husband Will and I have been making those decisions at pace for years now. Two careers. Four kids between us. A social calendar that could flatten a small government. Somewhere in all of that we landed on the one principle everything else in this article hangs off, which is: no surprises. Not about money, not about family, not about whose career gets the next big yes. We eventually built an app around the way we run things, Cupla, but the app came second. The conversations came first, and they cost nothing.
And look, here’s what I’ve come to believe about pre-wedding stress. It isn’t the seating chart. It’s the assumptions. The quiet ones two people carry into a marriage without ever saying them out loud. “Obviously we’ll do Christmas with my family.” “Obviously we’ll move if I get the promotion.” “You’ll keep handling the day-to-day stuff, because you always have.”
None of those are wrong, exactly. They just haven’t been checked.
The engagement window is the best timing you will ever get for this, because you’re both already in building mode. So treat these seven conversations to have before marriage the way you’d treat a cake tasting or a venue viewing, and give them an actual slot in the calendar. (Not engaged yet and wondering whether you’re ready? Start with when you should propose, then come back.)
1. Money: all of it, not just the fun parts
I’ll start with an admission. Finances are one of the greatest sources of friction in our relationship, and we both pride ourselves on being fairly financially responsible. Those two things sound like they can’t both be true. They can. We just have different views on how we save, how we spend, and what we want to spend our money on.
And here’s the strange part. I can’t remember a single moment where we sat down and had The Money Conversation, because we’ve been very open about it from the beginning. What I can point to are the rules that came out of that openness, the ones that help us navigate being different.
We made simple rules around spending limits. Under a certain dollar value, you don’t need to have a conversation. Over that, it’s a conversation. And it’s not so much that we’re asking permission from each other. It’s more of an informed conversation. We act on the basis of no surprises.
We also check in on how our savings are going, probably each quarter. I wouldn’t say it’s super scheduled, but it happens on a fairly regular basis.
The research says this matters more than almost anything else, by the way. Arguments about money are the top predictor of divorce, ahead of chores, in-laws, all of it. Grim, until you flip it around: if the two of you can talk about money calmly, you’ve taken your single biggest risk off the table.
The deeper stuff you only need to do once, but do it properly. What did money feel like in the house you grew up in? Tight, tense, never mentioned? What’s the actual full debt picture, including the car finance nobody brings up on dates? Joint accounts, separate, hybrid? What are we saving toward, and by when?
The prenup conversation
I think a prenup is a very, very powerful tool for couples, and I think women underestimate the importance and the power of one.
The way I’ve seen this executed well is when couples sit down and first have a conversation about the principles without any monetary values being attached; this is the essence of what you want the agreement to capture. For example; everything we build together is shared, what I came into the relationship with is mine, if we have kids, this is what I want to happen, whatever is relevant and important to you as a couple. It’s those wishes and your intentions that get captured by your separate legal teams. Once you start getting into the nuts and bolts and the numbers, you need those values you agreed upfront written down, so you can refer back to them and make sure the intention you wanted to capture is actually captured in the final agreement. That first part should happen without a lawyer in the room because it’s not a legal conversation.
Where prenups fall over is if there’s an imbalance of power or wealth, and the first draft comes from a lawyer without the couple actually having a discussion about it. That is a recipe for disaster.
2. Kids: the yes, the no, and the “maybe, eventually”
“Do you want kids?” is a starter question. Two people can both say yes and be describing completely different lives.
Will and I had this conversation very early on in our relationship. I was twenty-nine when we got together, and at that age it felt timely to have it upfront. It wasn’t something we would have wanted to delay, so it happened very organically. If your timing is different, you’ll have to be more deliberate about it, but the conversation is the same.
And go further than the starter question. How many, roughly when? What if it doesn’t happen easily, and where do you each stand on fertility treatment, on adoption, on fostering? Would one of you step back from work, for how long, and what does that do financially to the person who steps back? How were you each raised, and what would you keep or change?
And if one of you is a firm no, say it now. Not a hopeful “they’ll come around.” This is one of the rare topics where a real compromise doesn’t exist, so early clarity is a kindness. It won’t feel like one at the time. It is.
3. Careers, ambition, and whose life moves
Will currently splits his time between Mt Maunganui and Seattle. If that sounds like the outcome of a carefully negotiated ten-year plan, I have news. It happened really organically. We’d spent some time in San Francisco, we’d always wanted to get back to the Mount, and an opportunity came up.
We both love saying yes to things. That’s probably the truest thing I can tell you about us. Our general approach is that if a good opportunity comes up, we’ll try and find a way to make it work. So rather than saying “can we split our time between the Mount and Seattle?”, the conversation was more “how do we make this work for us?” That very subtle headspace shift is really, really important. One question invites a no. The other puts you both on the same side of the problem.
You can’t predict which opportunity lands, or whose it’ll be. A relocation. A pay cut for a career change worth making. A start-up that eats every weekend for two years. What you can sort out now is how you’ll decide, whose career has quietly been taking priority so far, whether that feels fair, and what the person making room gets back.
4. Family, in-laws, and where the boundary sits
This is the one I’d redo if I could. We’ve had pretty relaxed boundaries with family coming into our space (without invitation), and we probably could have established better communication about how that happens, much earlier in our relationship. And obviously, once you’ve set a pattern of how you interact in these situations, it’s very hard to unwind that.
I recommend agreeing on the basics before your first married holiday season; how do Christmas and birthdays get split? What’s the drop-in policy, do people ring first? How much do your families get to know about your money, your fertility plans, your arguments?
5. The invisible workload
Almost nobody argues about who does the dishes. They argue about who notices the dishes.
At ours it looks like this. I organise most of our social calendar, even including setting aside time for Will’s boys’ trip, golf, and his wellness. When he opens our daughter’s drawers, all of her clothes fit, and he never has to think about that. And the things I don’t think about? He organises the house maintenance. Mowing the lawns, window washing, paying the power bill, the rates bill, and everything to do with the cars; the warrant of fitness, the registration, making sure the washer fluid is full. I genuinely could not tell you the status of any of it.
Neither of us is the hero of that story. The point is that both lists are visible to both of us, so nobody is quietly running a second job the other one can’t see. When we surveyed our users, 59% said Cupla increased the sense of fairness in their relationship. That’s the stat that gets me, more than the flashier ones. Fairness is the one you feel at 9pm on a Tuesday.
So before the wedding, list everything that keeps your shared life running, the invisible bits especially, and divide it honestly. Then put it somewhere you can both see it. A plan that lives in one person’s head isn’t shared, it’s just delegated.
6. Time, energy, and what “us” actually gets
Every couple swears they’ll protect their time together. Then a busy season shows up, and the relationship becomes the flexible line in the schedule, because it’s the only commitment that doesn’t complain when you move it.
Will and I have a date night goal of once every two weeks. As it turns out, that’s roughly what the data likes too. In our survey of over 2,000 users, the couples planning around two dates a month were the ones reporting more closeness, more passion, more excitement about the future.
But here’s where I’ll push back on the internet’s usual version of this advice. You should always aim for non-negotiable, but it shouldn’t become a ball and chain. If one of you is unwell, or you’re both just not feeling up to it, you need to be kind to yourself and understand that life happens. It’s not about being perfect. It’s about going into things with the best of intentions. Protect it, but don’t let it start to feel like a burden if either of you, or both of you, are really not up to it. These things happen, and that’s totally okay.
Decide out loud what “us” gets. A night a fortnight? A no-phones dinner? One trip a year that isn’t a wedding or somebody’s family obligation? Alone time counts here too, and it’s worth asking how much each of you actually needs, so nobody hears rejection when the other one wants an evening to themselves. Then put it in the calendar (we’ve written more on making time for your partner here). A commitment with no date attached is a wish.
7. How you fight, and how you make up
This one gets skipped, and it might be the most predictive of the lot.
Look, like many couples, we don’t always get this right. What we do always try to do is take a time-out, or stop the conversation, if we can feel either of us getting into what I’d call the red brain. That’s when you become very reactive, and you’re in fight or flight rather than actually in your adult self. Nothing useful comes out of the red brain.
Quick to apologise. Always. Trying to use humour in the moment really helps, but in some cases that’s not available to you, and then it’s about removing yourself from the situation as quickly as possible and allowing yourself some time to get grounded.
Before the wedding, talk about this while you’re calm. When you’re hurt, do you go quiet, get loud, get logical, leave the room? What’s off-limits no matter what? For us it’s the usual list, exes, threats to leave, dragging family in. And what does repair actually look like, an apology, a hug, a joke, a bit of space? Naming your styles won’t stop the arguments. It stops the second argument, the one about how to argue.
How to actually have these conversations
The longer Will and I have been together, the fewer of these big conversations we’ve had to have. But early on in our relationship, it was literally: hey, let’s set a time to have this conversation, and this is what I want to talk about. You’re giving each other the capacity to consider the conversation before having it, so you both come to it feeling prepared, calm, and not in a reactive headspace. Springing “so, about your student debt” on someone at 11pm does the opposite.
One topic per sitting. Seven unhurried conversations will beat one exhausting summit every time.
Go in curious, not looking for a verdict. You’re trying to understand their answer, not win agreement for yours. “Tell me more about that” is the most useful sentence in this whole article.
Write down where you land, because memory is generous to whoever’s doing the remembering. And revisit, roughly yearly. Your answers at 29 won’t be your answers at 39, and that’s not a failure. That’s just people.
The work of being married
Most of our users are stepping into something serious with someone. Moving in, engaged, newly married. A lot of them, like Will and me, aren’t in their first serious relationship, and they want to get it right partly because they’ve seen what getting it wrong looks like. I find that motivating rather than sad. Nobody works a plan like someone who knows why the plan matters.
These conversations aren’t a test your relationship has to pass. They’re the start of the actual work of being married, the thousand small acts of coordinating and noticing that turn two independent lives into one shared one. Run on no surprises. Check the assumptions. Keep the conversations, and the date nights, where you can both see them.
The wedding is one day. This is the operating system for every day after.
It’s what we built Cupla to be. Our schedules side by side, the invisible work made visible, date nights that actually make it into the diary. 72% of the users we surveyed said the app made them more excited about their future together, and before a wedding, that’s the number that counts. It’s free to download on iOS and Android.
Erika started Cupla with her husband Will after realising how easily date night slips when two busy lives collide. Today she leads the company’s mission to give couples back their quality time — and still swears by a long nature walk and a table at a restaurant neither of them has tried before.
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