Breaking up

tags: post-mortem
  1. What went wrong?
  2. What went right?
  3. What could I have done better?
  4. What lessons should I bring from this relationship into the next?

Before I begin:

I undertake to be as honest as I can. There is a tendency when writing in a public setting to want to virtue signal, and I will resist that tendency at all costs. The purpose of this post is to use it as a platform for introspection and find out as much as I can what went wrong and how to improve. The efficacy of this post in achieving those goals drops precipitously if I use this post to excoriate her or to vindicate myself. So I promise to be as fair, honest and impartial as possible.

In fact, I explicitly want to bend over backwards to be charitable to her point of view for two reasons: 1) she is not here to defend herself, and it would be incredibly unfair to post misrepresentations or strawmen of her views; 2) we are self-biased, and all of this is from my perspective, which means that trying to be fair and impartial necessarily means being biased towards my own point of view.

I find writing about this incredibly difficult and exhausting; writing about relationships (at least the way I’m trying to do it) necessitates sharing my deep personal convictions (not so scary), my deep-seated insecurities (scarier), and my fundamental inadequacies (very scary). Even for me, writing about these things makes me feel very vulnerable and uncomfortable.

What went wrong?

After a lot of introspection and “extrospection” (speaking with many trusted friends), I think I have two possible explanations:

  1. I did not love Judy enough
  2. We had different, incompatible ideas of how love was expressed

I honestly do not know which one is the case: let me set out the case for both.

I did not love Judy enough.

How it must have felt for her! It was fine when we were both together in the same place, but dating long-distance was surely a disaster. She was dating someone who would take hours to reply her texts, claiming to not use his phone while doing “deep work”, and would only call her at night after finishing all his tasks. She felt like an afterthought: “let me finish all my schoolwork and gym and dinner and programming and a hundred other things before setting some time aside for you”. I was a very poor boyfriend.

A hopefully relevant anecdote:

After her graduation she moved to Seattle to live with a friend there while finding a job. Valentine’s Day was coming up; I wanted to send her something, but did not know her address. I asked her for her address twice, but she did not tell me. So on Valentine’s Day I bought some flowers, croissants (her favourite pastry), and baked some cookies, and video called her to “give” them to her virtually. As far as Valentine’s Day gestures go, I suppose this was a rather lame one, and I could tell that she was disappointed. We spoke about this afterwards, and I very reasonably pointed out that I could not have sent her anything without knowing her address, and I did not know her address because she did not give it to me even after asking her twice.

She didn’t have a reply to that, but I do. After much reflection, I think I know why she was very coy about it: she wanted me to work to get her address, as a signal of my love. If I really, really wanted to get something to her, I certainly could have. I could have been more persistent in my asking. I could have sent an FB message request to her friend, asking for her address, and I’m sure she would have given it to me. No, the reason why I didn’t send her anything for Valentine’s is not because she didn’t give me her address: it’s because I was lazy, and didn’t care enough to get something to her over and above discharging my duty as a boyfriend. In other words, I did not love her enough.


But I have a reply to that, too. Judy said that Valentine’s day was something very important to her, and so she was very sad and disappointed when I got her a lackluster gift. I told her that that’s all well and good: personally, I don’t care for Valentine’s Day, but I of course understand that different people care about different things, and we should do things that make other people happy. But I asked: why didn’t you get me anything for Valentine’s Day? After all, you know exactly where I live. She said she was busy preparing for interviews and so didn’t have the time to get me anything. I said: but didn’t you just say that Valentine’s Day was very important to you? She clarified: when I said Valentine’s Day is very important to me, I mean that it’s very important to me that I receive a gift from my boyfriend, but not very important that I give a gift to my boyfriend.

On first blush, this didn’t sit well with me. While I don’t mind not receiving anything for Valentine’s, I thought there’s something not quite right here. If Valentine’s Day is very important to you, then you should think it important that you get your partner something. For instance, if honesty is very important to me, I think it would be unfair to demand honesty from my partner while being dishonest myself. It seems like these values should be symmetric.

But on the other hand I see where she’s coming from. Traditionally it is the guy who makes these grand gestures and declarations of love. I think she put it very aptly: in her own words, an equitable Valentine’s Day is one where the boyfriend gives the girlfriend a very sweet gift, and in return the girlfriend gives the boyfriend a very sweet kiss. I may personally disagree with this, but in these subjective matters is there even right or wrong?


This nicely segues into the other interpretation for our breakup: we had different, incompatible ideas of how love should expressed. Under this interpretation, while I loved her and she loved me, we felt that the other person did not, which led to relationship breakdown.

How does one show their love for another? And how does one want to be shown love?

For me, love is about spending quality time with the other person. It is about making sacrifices for the other person. It is about being willing to compromise and change for the other person. It is also about physical touch and intimacy with the other person. I was frustrated because I felt that she was not willing to compromise on issues, or to make a charitable effort to see things from my perspective.

For her, love was about being present and available. It was about receiving gifts and about treating her nicely (“spoiling” her): in her words, 女生要被寵要被哄. She wanted a situation more akin to “the boyfriend plans everything and pays for everything”, or “the boyfriend should let the girlfriend win arguments”. She was frustrated because I did not seem to be available during my day, because I did not much like spending money, and didn’t give her the feeling she wanted of being doted on, protected and spoiled.

I genuinely do not think that there is any right or wrong in the conception of love. Maybe you think (as many of my friends have remarked) that her conception of love is somehow wrong because it’s very materialistic. That may be the case, but I suppose my friends are my friends because we think alike. I am sure when she conferred with her friends her friends were likewise aghast at how poorly she was treated by me: not doting on her at all, not doing the basic things that boyfriends should do — e.g. wanting to go Dutch on dinners, not buying her a gift for her birthday (I did give her a gift eventually — I made a photo collage of our time together — but it did indeed come after her birthday, which was definitely my fault), letting her do most of the planning for our holiday…

And in large part what we want from our relationships is shaped by our formative experiences and the culture we grew up in. To me quality time is very important, because my father was largely absent from our lives when I was a child, and I heard my mother complaining about how my father would not attend our graduation because he was too busy with work, and on the rare occasions that he took the family out for holiday he would be making conference calls and working on his laptop sending and replying to emails.

I don’t blame him — he was (is) working very hard to provide us with good lives; having spoken to my father now that I am older, I know he is a very filial son, and a very dutiful father. I know that he worked two jobs and brutal 16-hour shifts to afford the downpayment of our first house. Even now, he goes out to work early and comes back late. Why does he work so hard? I asked., He says that he wants to buy a big bungalow for all of us so that Yeye and Nainai and Popo can all live with us, under one roof.

My father is almost 60. I asked him when he plans to retire and he said “I will keep working until I’m 80”. I really respect that — god knows I don’t have nearly the doggedness or work ethic that he does. I certainly hope to be long retired by 60 (although hopefully still busy working on difficult, interesting problems).

But as my mother wryly remarked (and it is a view I agree with), we didn’t (don’t) need much: forget the big bungalow, just spend more time with your wife and kids.


I also had/have an irrational fear of spending money. I find it very difficult. The Great Recession happened around 10 years ago, and my father’s business went into ruin.

It was a tough time. I remember regularly coming home after school and seeing my mother in tears. We had no money to pay for anything. We couldn’t pay the mortgage on the flat, we couldn’t pay the utility bill. I overheard my mother on the phone with the school bus auntie. The auntie was chewing her out because we could not pay the school bus fare: 60 dollars (about 30 pounds?). “你們什麼家庭 連60塊都付不起”. As a young child I felt helpless and distraught at seeing my mother in this state. There was a lot of crying, a lot of shouting, there was talk of divorce, and I know my mother seriously contemplated suicide at that point in time.

Eventually things got better: my mother got a job as a tour guide, and since I received the scholarship both my mother and I have been able to be financially independent of my father.

But it’s difficult to overstate how big an effect this has had on my psyche. In fact I can trace my interest in early retirement to these two formative events. It is my hope that by living below my means and by investing wisely the surplus, I can give my partner and children financial security and quality time.


The main point of this digression was to show that my culture and upbringing has shaped what I want—and what I am prepared to give—from my relationships. It must be the same for Judy too. I visited her at her university, a liberal arts college in Maine. Her friends (and their boyfriends) were all very well-to-do, driving brand-new Bentleys and Porsches that they’d then resell after completing their degree and flying back home. I think it was also common for boyfriends to give Canada Goose clothing for birthdays and anniversaries. Here love is expressed by giving gifts and spending money on the other person. In this social context, could her conception of what love entailed be otherwise?

Much to her credit I never once heard her complain about my relative poverty. I am grateful for her sensitivity. She was however expecting me to compensate in other ways for my relative material deficiency: if the boyfriend cannot shower me with expensive gifts, then he should make up for it by being extra doting, extra caring, extra attentive, and I was none of that. I regret this, and should have done better.

To me, a big part of love is being willing to change for the other person, and I was able to fulfill this. This is why I felt unloved when she was unwilling to compromise and change for me, and possibly why I wasn’t able to muster up being extra doting/caring/attentive.

One might argue (as Judy did) that being willing to change for the other person is not love, as since what the other person wants you to change is usually objectively beneficial for you. So you are not changing for the other person, you are changing for yourself.

But I would argue that even changes that are objectively beneficial for you can be hard to make: think about how hard it is to make a habit to go to the gym regularly, for instance. It’s even worse when it comes to subjective matters. For instance, the view held by her (and many others, including my mother), is that the boyfriend should foot the bill. I can see where this view comes from, especially in a social context where spending money, just like spending time, is a show of one’s love. But I think one could reasonably disagree on the basis of egalitarianism. One could also believe that both partners should pay according to their ability, not their role in the relationship.

I think I showed my love for her by changing two things about myself over the relationship. Of course, I am grateful to her for sparking the changes.

First is the way that I dressed. Judy didn’t like the way I dressed; she said my clothes were ill-fitting and had weird patterns. Initially I thought “I don’t want to waste money on things that don’t matter: my clothes fit me, aren’t discoloured, and don’t have holes in them, I don’t see why they should be replaced”. But this bothered me much less than it did her, and I thought I owed it to her to look attractive for her, so I donated away many of my existing clothes, threw away my underwear and socks, and bought new ones. (We had an argument when she wouldn’t allow me to buy Primark underwear, which I thought was perfectly good, but that is tangential). This wasn’t a very difficult change to make; I only had to spend (not very much) money, and only a few articles of clothing were sentimental to me.

Fashion is of course a subjective thing, but some of my friends have told me that I dress much better now, so I have her to thank for this.

The harder change was to be willing to spend more money. As mentioned, I had somewhat of an aversion to spending money. Things came to a head when Judy gave me an ultimatum when I visited her in December: I had to stop being stingy, or she would break up with me.

That was probably the hardest change I had to make. I never cry (???toxic masculinity???), but that night I did. Rationally I knew that I was already financially independent and had a healthy surplus from saving up my scholarship allowance. But it was incredibly difficult to let go of the fear of having no money, a deep-seated fear branded in the memories of my childhood. I felt torn between my emotions and my rationality, which is why I felt very distraught and cried. Eventually I decided that if I loved Judy, I should be willing to make difficult sacrifices for her. So I transferred all my money from SG into my Monzo.

It was a difficult thing to do. Over our US trip I also felt heart pain when spending money. But I kept telling myself that I should not feel heart pain. I wasn’t able to fully get over it on that trip (probably because the numbers were so large), but afterwards in Oxford and my subsequent trips to Finland and Romania I was able to be much more relaxed in my attitude towards money. I’m probably still not over the hump, but I think I’m making good progress towards it. I want being generous, not stingy, to be my character trait, and I want to be open and 大方 with my friends and loved ones. I keep telling other people I have money — and while it seems like a very braggy thing to say (or an invitation to be robbed) — I am saying it for myself to hear.


On the other hand, I felt that she was unwilling to change for me. In her case one of the things I really wanted her to change was her tendency to react emotionally to things that were said too quickly. From my perspective, she would interpret something I said or pick up on subtle emotional cues, and get really mad, and have a temper and storm off. As someone who likes to sit down and talk rationally about things, I found this very frustrating, because I first had to soothe her and calm her down and basically admit fault (even when I was certainly not at fault) before she would be pacified. And when I tried to bring up the issue of whatever had sparked the argument in the first place, she would get angry again, thinking that I was trying to extract some sort of concession (or confession) from her. It was a little bit of both. I figured out that she was too proud to apologise and admit fault—the most I got was a sheepish smile and a hug—but I wanted also to address the issue that got us arguing in the first place.

Another thing was when we had arguments about something, and I would always do something like the following as some sort of debrief. I would say “in this incident, A happened because of reasons BCD. It was my fault for doing/not doing X. In the future, to prevent a repeat of A, I undertake to do Y.”

Then I would ask her for her thoughts and what she thought she could do on her part to prevent future occurrences of A. She really didn’t like that. I think we viewed it differently. To me, it was fair and helpful for both parties to compromise and improve, fault aside. But I think she didn’t want the relationship to be fair —“為什麼什麼東西都要講公平?”—because she expected the boyfriend to be the more conciliatory one. Again, I can see where that comes from, but to me it just felt like more evidence that she would not change for me. I suspect part of the reason why she was not as willing to compromise was because of our very different socioeconomic backgrounds. It was already a big compromise for her to step down and date me.

To her, love was about being doted on and being given attention and gifts. Because she did not see that from me, she became resentful. To me, love was about being given quality time, sacrifice, and compromise. Because I did not see that from her, I became dejected. In the end, we had different interpretations of how love should be expressed, which led to our breakup.


So which interpretation of the breakup is correct? I honestly don’t know. I think the answer hinges on what love is, and I really cannot answer this question.

Here’s one way to think about it. Because I did not love her, I was not willing to shower her with gifts and attention and let her win arguments. I didn’t feel a very strong emotion towards her. I wanted to get her a Valentine’s Day gift out of duty, not out of of love. Therefore, I had wasted both of our time, trapping her in a loveless relationship.

Here’s the other interpretation. I did love her— I was willing to compromise and sacrifice for her at significant personal cost. It is unfortunate, but no-one’s fault, that our expressions of love differed so greatly.

I have many questions I hope to eventually be able to answer:

What went right?

I should say that I regret nothing about the relationship. Bad things are more salient than good things, but if I cast my mind back I can remember having many good times with Judy.

As mentioned, I changed for the better because of her during my relationship, and for that I am immensely grateful. I also got to see a little bit of how people from very different backgrounds and socioeconomic classes are like, which was eye-opening. I think I have learned how to be more patient and more caring, although not enough to save the relationship.

I sent her this text when we broke up back in April, and I thought it neatly summarises:

We have been together for almost a year, and despite ending in a sad manner, I cast my mind back to the previous year and it fills me with happy, dreamy, lovely memories. My fondest experiences with you were punting in Oxford, my birthday night in Singapore, skateboarding in LA and taking adorable Polaroids at the Colby fall ball. In fact, the more I think back, the more things i want to add to that list. But the thing I loved most and will miss the most was just cuddling in the middle of the night, talking about our plans as we slowly drifted off to sleep. I still have the list of things we wrote down to do in the future: 看夜空, 滑雪, 吃豆腐宴, 吃豆腐宴…

That may never happen now. While I still love and miss you very much, there’s no denying that we are very different people with two very different notions of what romantic love entails. You take a more traditional view of gender roles in a relationship, while I am relatively egalitarian. While I’m willing to change, i) who knows if I can actually change, and ii) I know your patience has long ago been worn thin. Guilt still runs through my mind: what if I had tried harder; been more dedicated; loved more gallantly; acted more charitably? Sadly, it is too little too late. There are also other issues like you wanting to pursue a career in the US, while I have to go back in Singapore, and the fact that we come from different socioeconomic classes with different attitudes towards money. To me, a large part of love is duty and sacrifice, but also caring about the other person’s happiness. And I have to accept that if I truly love you, I should not bind you to a relationship that you feel unhappy in. I should let you find a better partner for whom pampering and spoiling his lover comes naturally, rather than someone who has to work hard to do it.

We are very different people, but this makes me even more grateful to have known and dated someone who’s almost from another world —- a much higher social class, with an upbringing and experience far removed from mine. It has been an eye-opening experience for me. From the bottom of my heart, I thank you for the good times that we had and for the many, many things you’ve taught me. Despite the fact that you were feeling tired and drained towards the end of the relationship, I do sincerely hope that you found our relationship on the whole a happy, positive, and constructive one.

How could I have done better?

I should learn to be more caring and loving. Maybe I was adequate, maybe I wasn’t — but it’s surely strictly better if I’m more of both. Unfortunately I don’t know how to do this. Some of my friends have suggested that when I find “the one”, I’ll automatically want to care for them and dote on them, etc. I don’t know if this is true. Also by modus tollens, if I don’t feel like I want to dote on them and care for them, does that mean I don’t love them/ they are not “the one”? Scary if true. Is “the one” even a coherent concept? Or can everyone be the one for you, you just need to work more or less hard to be together?

I’m not sure what the best way to approach arguments should be when my partner gets angry with me, and I don’t agree. Initially I thought that the best approach would be first to mollify, then to bring it up — but I don’t think this approach led to much success…

I am by nature a very argumentative person, keen to argue about small things that don’t even bother me, but just to get the truth/the reason behind a person’s views. I realise that this can be frustrating to people, and it’s often better just to let things slide. The problem is that I have trouble distinguishing what would be an interesting disagreement to have for a conversation, and what would be a relationship-fraying disagreement. Or maybe it’s not the topic, it’s that person’s state of mind…?

Lessons for the next relationship?

I learned that I should be much more judicious in choosing the person I want to date. Judy and I were very different people: different enough such that I wasn’t able to love her (interpretation I), or different enough such that we had radically incompatible notions of what it meant to love and be loved (interpretation II).

I may be relying too much on notions of duty here: “I should be more loving, should be more gallant, should be more understanding”. But maybe if I found someone more compatible with me, I wouldn’t need duty to do those things. Maybe if I found someone more willing to have arguments without taking them personally, I wouldn’t have to be understanding. Maybe if I found someone intellectually curious about the same things as I was, checking in on each other would be more organic and enjoyable. None of this should be read as an indictment of her; if anything, it should be an indictment of myself, seeing that I wanted to date her without first checking if we were compatible in those other ways.

But those are just maybes. Whatever it may be, I want to learn how to be more loving, gallant, caring, doting—just like I needed to learn how to dress better, and be more generous with my money, and just like I learned in the past how to be less callous, more honest, and more introspective.

Love is mercurial and difficult to pin down, but I want very much to get it right.

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