Preamble: Hello everyone! This post has been getting shared a little bit, so I thought it might be worth taking some time to put together a bit of context? This blogpost is basically a “cleaned-up” or “unrolled” post of 5 of my Twitter threads. I put this together because I think it’s a useful thing to share with friends who are engaged, or newly wed.

1. There are reliable indicators that predict relationship failure

(The following thread was something I wrote off-the-cuff, like most of my threads, but it ended up getting almost 1,000 retweets.)

My wife predicts divorces & failed relationships with stunning accuracy and I have learned a few of her tricks.

Relationships are fucking hard, and to work they need a sort of functional “economy” (gratitude, laughter, kindness) and waste elimination system (pain, resentment).

Relationships typically fail either because the economy died (no happiness) or the trash pileup in the street made it inhabitable (too miserable to function). Both have symptoms & warning signs you can look out for. (My wife notices these YEARS before I do; it’s insane.)

Just as how “the score takes care of itself”, there are some fundamental, structural things that need to exist in order to manage a relationship’s economy. These are the equivalent of things like rule of law and a reliable money supply. It’s especially necessary for weathering inevitable disasters.

“How will this couple handle a year of unexpected misery, caused either by one, both, or neither parties”? Will they talk about it honestly & openly with each other? Do they really listen to each other? Do they speak of each other with tenderness? Do they build each other up?

A serious relationship is a massive undertaking, a heavy burden on your back. It’s like lifting weights, actually. You need to have good form. You can tell when someone has bad form, the weight is going to fuck them. But do it well and you get stronger.

Spending a lot of time together doesn’t nearly mean as much as people tend to assume it does. Your relationship will die if you *don’t* have any quality time together, but simply spending lots of time together doesn’t guarantee anything. Spending a lot of money (that you can afford), going on fancy vacations together, throwing a fancy party (ahem: weddings) all don’t mean much. All of those things are actually relatively easy and trivial.

The “killer” signs:

• Contempt. Doesn’t matter if you’re laughing as you jokingly put each other down. One day it won’t be funny.
• Dismissiveness. “Ugh, she’s always like that”
• Indifference. “nah it’s nbd whatever”
• One partner constantly apologizing for the other. This is not sustainable.

This is bad form – when the hard times hit, they’ll buckle.

I find that you can often infer quite a bit from a couple’s body language and eye contact. A couple that is close will make eye contact often. Not necessarily stare lovingly into each other’s eyes (my wife and I actually don’t do this much), but just “re-sync” regularly to get frequent snapshots of each other’s state.

A sad warning sign: when one person has to constantly apologise for the other. It’s usually women apologising for their boyfriends. Don’t do it. It rarely gets better. If often gets worse. And y’all often put up with it for years longer than you should. Let him go sis

You weren’t put on this earth to apologise for somebody else! You don’t have time for that. It’s a full time job apologising for yourself!

^ see, this is a joke that doesn’t put anybody down. Anybody who needs to make other people feel weak/small/foolish etc is a red flag.

Also, while being rich won’t guarantee relationship success, one of the biggest causes of divorce is financial conflict / debt-related frustration. Getting it right isn’t enough, but getting it wrong will cost you.

“Can you explain more about the resentment?”

Sure! Basically, in a marriage, you’re going to have to deal with the costs incurred by your partner’s mistakes. THEY forgot something, THEY messed something up, you did your part but THEY didn’t. This is painful and frustrating.

It will become easy to get angry & frustrated with your partner – especially since you’re in such close proximity and your actions impact each other so much. So you need a system to acknowledge, address and resolve all this pain and resentment. In my opinion, this is more intimate than sex.

I’m not saying I’m an expert. I just have some experience to share. Nobody’s perfect. But if you want a good shot at making things work you gotta do your due diligence & check in, regularly, even when you’re tired, especially when it’s hard. It’s very easy to overlook this. Acknowledge the mess and work at it.

There’s a relationship death spiral that goes like this:

1. You’re tired, so you hit snooze on difficult conversations
2. your backlog from 1 is overwhelming
3. You start spacing out in each other’s presence (how was your day? fine). You’re not really there for each other any more. Life is now just a series of tedious chores you have to do.
4. The “spark” is gone.
5. Since it’s all chores and the spark is gone, you’re subtly colder and more uncharitable towards each other. You’re both play-acting corporate shells at this point and it’s very unpleasant.
6. This buildup of resentment and frustration ends up being ignited in a fight over some trivial thing like dishes or laundry. Hint: It’s never really about the dishes or the laundry. It’s about the relationship.
7. Everything gets worse, and the cycle worsens. The fight leaves you feeling exhausted, which brings us back to 1.

So the meta skill is to recognise that this is a spectrum. There’s an Esther Perel quote that goes, “passion waxes and wanes, but erotic couples know how to bring it back”. This is likely unique to each couple. But you can see it and you can feel it when you’re in the presence of a couple: how open and psychologically/emotionally intimate people are with each other. (Funny Wanda Sykes bit about the Obamas.)

Just to emphasise: we never root for any relationship to fail. Life is hard and love is precious, and we want all of our friends to flourish and be happy. It’s just unfortunate that people are so often unprepared for the work. May you all nourish + be nourished in every way. ❤️

2. Your spouse will frustrate you more than anybody else

Wife and I were laughing about this last night: the thing nobody quite tells you about marriage is: you’re choosing the person in life who’s going to upset, disappoint, annoy and frustrate you more than anybody else.

This is true even if your spouse is the least annoying, frustrating, upsetting person you know! Because of base rates. For example, suppose the average person has a 10% chance of annoying me, and my wife has a 1% chance. I still hang with my wife much more than 10x than the average person.

Spouses get to see the worst sides of each other more than anybody else, and so it’s very easy for people to learn to think more poorly of their spouses than other people – which is sad because there’s a sort of optical illusion / selection bias at play.

Marriage is the first relationship in your life that’s anything like marriage. Nothing quite prepares you for it. When you’re dating, you’re not yet *entirely* subjected to the consequences of the other person’s actions or inaction, and walking away is a cheaper option

Also this probably varies from culture to culture, but other people’s assumptions and expectations become a big deal. Families expect things of wives that they don’t expect so much of girlfriends. Women often seem to get the short end of the stick on this one.

For us, humor is central to keeping things interesting, fun, compelling. You’re not going to escape pain, but if you can laugh about it together (caveat: not contemptuously at each other) then it’s still fun.

3. Marriage is hard and requires deliberate project management

On the project management of a marriage, which is something I’m still not very great at + always trying to be better at.

The following is from an impromptu Q&A I did with a researcher friend:

“How do you organize your schedules?”

I’m kind of sloppy about these things. I make plans but I don’t always follow them. I tend to plan social meetups on Facebook Messenger, then add them to my Google Calendar once it’s confirmed. My workdays are defined by my work tools — Trello, Slack, Gcal.

My wife has access to my calendar; she needs to know if I have after-work plans, or weekend plans. We also plan things together sometimes. We figure it out over chat and then we update Gcal accordingly. We also have a personal Slack channel where we go through everything more thoroughly.

“It sounds like you put in quite some effort to sync your schedule with your wife’s. is this important to you?”

Well yeah, we have a finite amount of time together, so if we’re out of sync it sometimes means someone is left in the dark, unexpectedly alone, lonely without plans.

Once you’re married, there’s a very large volume of things you have to care about — everything from dental appointments and family obligations (two sets!) to household maintenance. Slack is great for this because you can have multiple channels for each concern and not lose track. But you can use whatever; as long as you have a system that works for both of you. (We were both already using Slack at our respective companies, so it was a small thing to experiment with making our own, for fun. And it turned out great.)

Can you tell me a little more about how planning your everyday life compares before and after marriage?

There’s a line from an article that goes, “You’ll find yourself wistful for the days when you had to pay for only your own mistakes.” It’s like that. Each of your mistakes are going to cost both of you now. Sometimes you’re going to do (or fail to do) something, and you don’t just disappoint or upset yourself — you have to deal with the fact that you upset your spouse. Some people can’t deal with this, and get angry at their spouse for being upset. And boom, one of the many spiralling vortexes leading to marital failure.

Before marriage, you are less of a joint unit. Cohabitation is a big part of that — most Singaporeans don’t cohabit before marrying. But even if you do cohabit, after marriage, you each subtly start to feel more obliged to be a bigger part of each other’s life. (Of course this varies from couple to couple, some married couples are somehow super independent. I know one married couple that’s like long-distance half the time. I don’t know how they do it.)

An evil thought that arises after you’re married & have your first married fight — you don’t HAVE to apologize. You don’t HAVE to sayang & manja them. I mean, you probably will, out of habit, but you could also be like, “fuck it, suffer, I don’t care. Whatcha gonna do, divorce me?”

The fact that the cost of walking away becomes so much higher permanently alters the relationship dynamic. The cost/benefit calculus. anybody who says this doesn’t affect them at all is either lying or very ignorant (or has attained Enlightenment.)

Their problems are now your problems. There’s all this family stuff — which of course varies from couple to couple too. Like, if your parents-in-law are being difficult or something, you can’t really be like “Well ok, good luck, not my problem, I’m going bowling with the boys,” or whatever. You’re obliged to deal.

Once you get married, it’s like your relationship is now in a smaller room. It’s cosier, but you also can’t yell or make as much of a mess as you could before. You could theoretically try, but it almost definitely will hurt the relationship. The skillset that gets you INTO a relationship is very different from the skillset you need to sustain one.

“Would you say that you map out ‘unfilled’ time with your wife? how do you plan/negotiate that?”

Our default state is a sort of vague coexistence — usually involves both of us hanging out at home and each doing our own thing, me catching up on work or reading/writing. over time we’ve learnt to be more explicit and deliberate about making requests of each other.

We usually discuss things at a “what needs doing?” level, and then once we’ve agreed that something needs doing, we put it in a calendar and try to follow it. Keyword: try. Hahaha.

Something we’ve been trying to be more rigorous about is having explicit time set aside purely for dates or couple time. when you first get married, you’re around each other so much and so focused on each other, it feels like you don’t have to. but you gotta do it. vvv important.

“How does explicit couple time differ from “vague coexistence”? why is planning that so important?”

Right. It’s possible to vaguely coexist together for WEEKS, waking up, having lunch together while each of you is on your phone, replying to friends, work emails, having dinner together watching netflix, visiting parents, going thru the motions… and subtly drift out of sync.

By “out of sync”, I mean that each of you has a fresh set of concerns and worries that you haven’t articulated to your partner yet, because the mere act of articulation is going to be a tedious process.

That’s when you start responding to questions like “How was work” with “ok la the usual” — because you don’t want to go through the trouble of explaining what was bothering you. (This is why it’s useful to have a #feelings channel in your family slack, so you can just post your feelings as you go… Now that’s a life hack!)

Getting “synced up” as a couple is tedious, even when it’s with your best friend of 15+ years. You have to negotiate things. You have to talk about feelings, and frustrations. it’s always easier to be like “aiya later lah, i’m so tired.” You know in advance there’ll be disagreement.

“Can you give me an example of friction points and sync difficulty?”

A simple eg — say we’re both frustrated with our shitty old sofa + we both know we want to get rid of it. But talking about it means Having A Conversation. Because we each have different preferences, different styles. I’m happy to toss it + make do. She’d want to review options.

Negotiation is tiring, even when you both know exactly what the other person is going to say — because then you kind of have to do this waltz of feelings and considerations. It requires being alert and aware and sensitive to each other. Otherwise it means being disrespectfully dismissive, and that’s the sort of thing that ruins marriages.

So the easy thing for both people to do is to defer the conversation. “Remind me later”. That’s the 2nd worst outcome, you just quietly get increasingly frustrated with the suboptimal mess you call your lives. The worst outcome is a fight, because one person badly wants to do something and the other really doesn’t want to deal with it. How you handle this, while tired af, is the heart of marriage.

& I’m describing one of the simplest, most trivial friction points! Literally Every Imaginable Thing is a potential friction point in a marriage. A sofa is just an object. You’re going to be having intense, difficult conversations about much more personal, contentious things. Imagine if you add kids into the picture! So it’s insanely important that you both be good at doing this, believe whole-heartedly that you’re on the same team, and be kind to each other.

If you don’t have a system You Are Fucked. In the absence of a deliberately designed system, lots of families seem to defer to an improvised system of yelling, screaming, guilt-tripping, emotional blackmail… unimaginable cruelty because of a terrible system of management. It’s very sad.

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There you go, a tiny little taste of what marriage is like. It’s really hard, but it’s also one of the best things in the world when you get it right. When you’re really in sync (or even when you’re not, but you trust each other to take care of things), you feel really wholesome, fulfilled, nourished.

Feel free to tag your engaged / long-dating / soon-to-be-married / newlywed friends, I know I wish someone had written this sort of thing for me when I was freshly wed~

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PS: Do 1–1’s

Wanted to reiterate — a very clever and effective way of dealing with the inevitability of friction points and sync difficulty is to schedule 1–1 meetings in advance. This is an idea I stole shamelessly from work. Basically, have some time set aside (at least once a month) for the EXPLICIT purpose of discussing difficult things. This has several benefits.

1. You don’t need to feel bad about interrupting your spouse with what’s guaranteed to be a frustrating discussion.
2. It lets you compartmentalize better, so you don’t need to be quietly fuming at each other the rest of the time.
3. It also means that when you’re having an argument, you can just have the argument and not have a meta-argument about how badly you are having the argument. That meta-argument can be had during the scheduled 1–1s.

It might sound oddly bureaucratic, but it’s a huge lifesaver/relief/anxiety-reducer. A lot of couples I talk to tend to get stuck in the meta-argument loop: they have some problem they need to solve, and whenever the argue about it they end up also arguing about how badly they’re arguing — and since they’re already in a bad mood, they struggle to be receptive to one another. Few issues are perfectly 50/50, so getting into a meta-argument always feels like a derailment of the original issue. AND the original issue never gets resolved.

This is a misery I wouldn’t wish on anyone. (And yet it’s probably super common in lots of families.) Compartmentalize your arguments, and schedule time to have them in advance so you’re not caught off guard. It’s also a great excuse to treat yourself to good coffee or beer, and go on long walks, etc.

4. It is *necessary* to become more considerate as a relationship develops.

The longer a relationship lasts, the likelier it is that you’ll step on each other’s toes in recognizably repetitive patterns. The longer this goes on, the more hollow of an excuse “I wasn’t thinking” becomes. It thus becomes *necessary* to become more considerate.

Here’s a maybe-unpopular opinion I have: I think lots of people end their relationships because they lack the will or the ability to modify their own behavior. It is easier to start over with someone else than to do the tedious, uncomfortable work of adjusting for each other.

Of course, this is NOT to say “you should change who you are just to suit your partner” or “you should force yourself to stay in unhappy relationships”. Definitely not! That is bad! Rather, I think it’s important to be mindful of the patterns of behavior within the context of a relationship.

The pattern I’m describing is:

1. start a relationship
2. enjoy the good times and good vibes
3. accumulate “debt” from bad times and bad vibes
4. fail to address the debt; either avoid it or mishandle it (which makes it worse)
5. be overwhelmed by the scary debt, ditch the whole thing to repeat the pattern with someone else

A lot of pop culture takes on love is all about the good vibes and romantic gestures – about finding a soulmate who “gets you”. But even if/when you find that person, you’re going to piss each other off! and you have to figure out how to deal with that!

There’s of course also a “prisoner’s dilemma” aspect to this whole thing. What if you change to be more considerate of your partner, but they don’t return the favour? That’s an injustice. It’s not fair if one person does all the work and the other person gets to enjoy it for free.

Early on in a relationship, when you’re still sussing each other out, this is understandable – and the way forward is to make small changes then look for reciprocity.

In a long-term relationship, if you can’t trust your partner… what are you doing? You’re very possibly wasting your time. Or your standards are so low that you’re willing to tolerate an untrustworthy partner because you’re scared of being alone.

Circling back to the start: “I wasn’t thinking” is a hollow excuse even if it’s true!! I feel like nobody really talked to me about this. A relationship is a commitment to doing the work of becoming a more thoughtful person. You have to think more!! This is challenging!!

Sometimes people ask things like, “aren’t you afraid you’re going to get bored of each other after a decade?” There are some 🤔 buried assumptions in there. I met my wife in 2000 and honestly she gets more interesting every year. I’d like to think the same is true for me. For the beginner, interestingness is about novelty. For the expert, interestingness is about nuance.

Finally – I think some long-suffering couples solve the “stepping on each other’s toes” problem by basically avoiding each other, and keeping to a highly-choreographed routine. To me this sounds like hell, but for some people maybe it’s heaven? Do what works for you, I guess.

Anyway, as always, I am not an expert or a counsellor or anything of the sort – just a nerd who overanalyzes everything and has some thoughts and experience to share. May you all nourish and support each other in all the ways you need to be nourished and supported.

5. “Spicing up your relationship” is really about finding ways to be vulnerable with each other.

I have an essay draft making fun of the idea ‘how to spice up your relationship’ – people think it’s about toys and lingerie but it’s really about exposing vulnerable bits of your psychology to one another. You can love someone for decades and marry them and still have huge blind spots.

Relationships become boring because they get reduced into shell-scripts, patterns and routines – because people avoid the difficult work of communicating hard, painful things to one another. At this point some people, desperate for stimulation, do crazy shit like cheat.

It’s actually entirely possible to have an affair with your own spouse – just literally decide to break from your routine and ask each other questions about things you don’t normally talk about, and be honest with each other. Do hard and scary things together.

I think a big reason lots of people fail to do this is because they’re shy! You can see your spouse naked, and witness each other throwing up, etc – and yet be too shy to ask each other things that are outside of the stable/familiar configuration you’ve established together. You’re scared that they will judge you for wanting something different, for wanting to be someone different than they’ve gotten used to.

It’s easier to be a different version of yourself with a different person. You can open up your heart completely to a stranger at an airport that you’ll never see again, but you might worry about the consequences doing it to someone you have a long-standing relationship with.

So… the challenge is to mitigate the consequences, whether real or perceived. Most people are probably overestimating the negative consequences of talking openly with their partners. But some people might not be. Something to think about.