My Uphill Journey and Reflections To Marriage Through The Late 20s
14 Feb 2026 marked my fifth Valentine's celebration with my husband as a couple, and two plus years of marriage. During a simple Korean dinner that evening - after a spectacular Cirque Du Soleil performance he'd surprised me with - I remarked with bemusement that we've now been married longer than we'd been dating. Funnily, dating felt longer.
In this post, I want to share the (possibly) unconventional approach I took in my late 20s towards settling down. It is a topic I’ve always meant to discuss because of the weight I accord to marriage, the long journey of self-discovery I took, and the pressures I know are felt by others - particularly at milestone ages where the expectation to start a nuclear family is strong.
My hope is to shed light on one approach, my learnings, and let anyone struggling with this weighty decision know that you’re not alone. I hope you find the courage to pursue what is important to you, be it marriage or something else.
(Pictured below: Pre-wedding photoshoot in Bali, 2023)
Despite its profound impact, the path to marriage draws divisive views. Some prefer to encounter it by chance; others through hard work and reflection. I eventually chose the latter. I’ve had acquaintances remark how I seem to have invested a lot of thought into it since my late 20s, being ever the thinker. Below, I’ve summarised my experiences and ongoing reflections from that intense search for 'The One' during my post-breakup years between 2020 and 2021.
Note: This post constitutes my humble and imperfect views only. I hope they offer some consolation and perhaps some questions to start with!
How Our Background Shapes Our View of Relationships
I think it's important to recognise how childhood and past baggages shape our view of romance, as that clarifies the essence of what or who we seek, and whether that's healthy or continues to be relevant today.
Growing up in a relatively chaotic family environment and struggling with ostracism as a teenager, romantic relationships became my emotional backbone. In hindsight, I recognise how this shaped my decisions - both in entering relationships and in failing to exit them when they were no longer healthy. I stayed in dynamics where I lacked attraction, held vastly different values, or where we were constantly tearing each other down, simply because I feared my world would 'collapse' without that permanence.
In my late 20s, I made a decision that would break me for years. I let go of a partner I thought I truly loved because I was 'losing' myself - my dignity, peace, and values. It was the most courageous thing I could have done: letting go of a path that steered me away from self-actualisation. Knowing my future husband was the only family member I could choose, I wanted a safe space. That meant first letting go. The knowledge that I would inevitably 'lose myself' if I did not exit was the straw that broke the camel's back.
Letting Pain Become My Resolve
Instead of simply marinating in despair, I decided to let pain become my resolve through four intentional pillars:
3) Embarking on self-healing and discovery: I also embarked on other self-healing and discovery platforms such as, at the time, hypnotherapy and online classes to de-programme my past traumas and enrich myself. Through further self reflections, there was a growing realisation that it wasn't that we were 'bad' people, but that we chose people who were 'bad' for us. As one who aspired toward Maslow's state of 'self-actualisation', I sought a marriage that embedded the conditions for us to both flourish, such as a safe space for emotional honesty, vulnerability, and acceptance.
4) Being courageous and explorative: Being open to love meant being open to failure and heartache. Since I had already overcome the mental hurdle of undergoing paid dating services, I decided to be exploratory on the various social platforms and apps, conversing with and meeting people I would otherwise never have just to 'scratch a curiosity' and inform me of my preferences. As unpleasant as some of these interactions were, they helped shape my marriage decisions later.
The Reality of Paid Dating Services
Paid dating services carried a stigma that they were for 'undesirable' people, especially among young Singaporean millennials. I carried those beliefs strongly. What changed this was the combination of lived experience (having ended three long-term relationships that started more naturally), hearing about some positive experiences, and weighing the odds of finding a partner by myself vs assisted support within a specific timeframe.
Social Platforms & Dating Apps
During 2020-2021, I also used many dating apps such as Tinder, Bumble, and CoffeeMeetsBagel. I became much more exploratory - conversing with people I didn’t usually feel comfortable with - because hey, none of my past relationships had worked out!
I also interacted with people who slid into my social direct messages (DMs) and even dated someone from there for a few months. We explored religious classes together, but eventually parted ways due to different life views. What started out as physical attraction affirmed me that looks alone do not keep people together.
Ultimately, I found my husband on CoffeeMeetsBagel. I was apparently in his explore page and he’d paid 'beans' to talk to me ahead of schedule!
Reflections Through Dejection: Luck vs Effort
At my lowest point, my elder sister asked: "Have you ever wondered if it ultimately comes down to LUCK? Do you want to find your '100%' or do you want to get married by a certain timeline? Because the answers might look very different." That sobered me. Thinking through the people I had been drawn to or marriages I aspired towards, I realised a '100%' might not realistically exist. I drilled down into what I could accept and what I could not, leading to my Personal Criteria List where I looked for someone who met ~85% of the following:
My Factors to Consider: 1. Looks, 2. Financial Fitness, 3. Personality, 4. Education, 5. Health, 6. Personal & Family History, 7. Religion, 8. Ethnicity, 9. Relationship History, 10. Intellect, 11. Values (Non-Negotiable), 12. Emotional Connection/Support, and 13. Gut Feeling
For each of these factors, I had a rough idea of my preference. Under the 'Intellectual' plane, for instance, I was looking for someone who appreciates learning and demonstrates intellectual curiosity. I was thus drawn to my husband on our first date when he shared the latest philosophical book he was reading. There were also factors I did not include in the list, like 'View on Kids' or 'Love Languages', as they weren't important to me or were already represented by extension.
I further drew up a complementary '7 Questions Checklist' - adapted from a YouTube self-help video on romance which I resonated with - to help evaluate compatibility from a more emotional perspective. (I kept a physical list of this in my purse, as a reminder, when I went on dates!)
The '7 Questions' Stress Test:
1. Do you personally find him/her attractive?
2. Is he/she capable of and willing to adapt to your activities?
3. Does he/she help you self-actualise?
4. Is he/she worth it at his/her worst?
5. Is he/she ready for a relationship in his/her current state?
6. Does he/she make you feel emotionally secure across social and life situations?
7. Is he/she respectful of (or aligned with) your spiritual/religious views?
The Silver Lining Of A Longer Journey
There were two things that bothered me most in the search for marriage. First, it was the unavoidable anguish of my third heartbreak. Second, to accept that I had to take a 'longer road' while many Singaporean females were settling down in their late 20s - the exact point at which I was starting over. I don't want to skirt over these, because they were as much my pain as they became my resolve.
I got through my heartbreak by keeping my eye on the 'long game'. A meme I saw on social media perfectly captures its essence: Being single is one step away from a good marriage, but being in a bad relationship is two steps away.
As for the longer journey, I anchored myself in the 'Goldilocks' research on marriage. The research suggests that the ideal age for marriage is between 28 and 32; it balances emotional maturity and life experience with the flexibility to adapt to a partner - avoiding the higher divorce rates of marrying too young (<25) or the slightly increased risks associated with the mid-to-late 30s. Since I was in my late 20s when I broke up, I knew I had a few-year horizon to find my 'one' within that window. For every reason to feel defeated, I looked for evidence to keep my spirits up.
Other Reflections From the Search and 2+ Years of Marriage
Even with intense preparation, I don’t believe we can ever know with absolute certainty who to marry. This is because marriage isn’t a destination, but the start of a long journey between two evolving individuals. Recognising that it's unlikely for anyone to meet '100%' of our criteria required a serious evaluation of trade-offs - a process that, for me, took long periods of reflection and seeking out diverse perspectives.
1. Marriage is a CHOICE we are empowered to make: When presented with the sobering question of finding my '100%' vs marrying by a certain age, I realised my ideal and reality didn't match. I had never encountered a '100%', but I did know I wanted to be married. For context, we might love someone but realise we haven't grown into the same life conclusions yet, or we might love someone who meets only some of our important criteria. This empowers us with a choice: marry with known trade-offs, hold off, or choose a different relationship structure entirely. In my late 20s, I firmly wanted to settle down; that clarity helped me refine my criteria and choose a person I knew I could accept and love.
2. Choosing love means choosing a DYNAMIC: My '7 Questions' checklist was inward-facing because I believed that the choice of partner can shift the entire trajectory of one's life. Hence, a sustainable relationship to me is one where both partners mutually benefit in ways that build toward their self-actualisation. My most painful breakup wasn't because I stopped loving my partner; it was because staying would diverge from my desired path in life.
There is a saying that we are the average of the people we are closest to, and this rings especially true of a life partner. I’ve learned it’s not just about who our partner is, but who we collectively become. As someone seeking peace from my own competitive and anxious energies, I came to appreciate an equanimous partner who valued my zeal. As a 'T' dimension on the MBTI, I couldn't 'run' from reason; I recognised that all my past breakups were rooted in logical long-term incompatibility. I used the forced reflection of Covid and burnout to see myself clearly - my pain points, vulnerabilities, and boundaries. I realised the right relationship should improve, rather than weaken, my relationship with myself.
3. It is important to FRONTLOAD difficult conversations and factor in imperfections: Marriage meets us where we are, not where we hope to be. As much as we strive, we may never be perfect or free from our baggages. I found it useful to be transparent about our imperfections and what we needed early on so they could be factored into the consideration of marriage. For example, I recognised how teenage social rejection shaped my sensitivity to perceived threats; I needed a partner who was deeply affirming and communicative. Conversely, he was transparent about a genetic condition that required us to seek counseling early on. Because of my health-driven lifestyle, we also discussed an adjustment of his habits to assure me of our future together. These weren't one-off talks, but an ongoing dialogue about trade-offs and how we complement each other.
4. Marriage is a societal construct, but how we DESIGN the approach is up to us: Learning about the history of marriage - which allegedly began around 2350 B.C. for property and alliances, rather than love - was deeply freeing. Instead of conforming to established norms about what marriage should look like or our gender roles within it, my husband and I articulated our own expectations. We viewed marriage as a choice based on mutual consent and continual discussion as we evolve, rather than an outdated obligation. As avant-garde as it sounds, we agreed before marrying that we were not 'obliged' for the marriage to last. It is something we hope for and work toward insofar as love and compatibility exist. This is why 'values alignment' was the most important part of my checklist.
5. We can never be 100% certain, but we can take THOUGHT-OUT LEAPS of faith: During marriage education, we were cited high divorce rates of >20% in Singapore and >40% in the States. Rather than feeling dissuaded, I saw these statistics as a reminder that we can never know for certain. Knowing the pitfalls helped set a realistic expectation: this decision is ultimately a leap of faith. When it came time to decide, I leaned on the parameters I had set, knowing this path would lead to the least regret.
Conclusion
My journey towards marriage wasn't a straightforward path. I chose to do things differently even if the outcomes were not guaranteed. While tough, I do not regret this journey because I know it ultimately allowed me to grow.
If there were one takeaway I would like my readers to have from this experience, it is to be courageous in the face of uncertainty for things that truly matter to you. It is to try, especially if the risk of not trying outweigh the risks of doing so. Nothing in life is guaranteed anyway. So, too, marriage and relationships. But what stays with us, regardless, is the journey of growth and striving that ultimately define us and many other challenges we will take on in life.
Life is short and our years so important. So go, live it! <3
Sincerely, Meng Yee
In this post, I want to share the (possibly) unconventional approach I took in my late 20s towards settling down. It is a topic I’ve always meant to discuss because of the weight I accord to marriage, the long journey of self-discovery I took, and the pressures I know are felt by others - particularly at milestone ages where the expectation to start a nuclear family is strong.
My hope is to shed light on one approach, my learnings, and let anyone struggling with this weighty decision know that you’re not alone. I hope you find the courage to pursue what is important to you, be it marriage or something else.
(Pictured below: Pre-wedding photoshoot in Bali, 2023)
The Significance of Marriage
Why this topic? I see the modern construct of marriage as one of the most important decisions a person can make: it quite literally affects your health, wealth, and whole being. Choosing 'wrong' seems worse than not being in one at all.
Despite its profound impact, the path to marriage draws divisive views. Some prefer to encounter it by chance; others through hard work and reflection. I eventually chose the latter. I’ve had acquaintances remark how I seem to have invested a lot of thought into it since my late 20s, being ever the thinker. Below, I’ve summarised my experiences and ongoing reflections from that intense search for 'The One' during my post-breakup years between 2020 and 2021.
Note: This post constitutes my humble and imperfect views only. I hope they offer some consolation and perhaps some questions to start with!
How Our Background Shapes Our View of Relationships
I think it's important to recognise how childhood and past baggages shape our view of romance, as that clarifies the essence of what or who we seek, and whether that's healthy or continues to be relevant today.
Growing up in a relatively chaotic family environment and struggling with ostracism as a teenager, romantic relationships became my emotional backbone. In hindsight, I recognise how this shaped my decisions - both in entering relationships and in failing to exit them when they were no longer healthy. I stayed in dynamics where I lacked attraction, held vastly different values, or where we were constantly tearing each other down, simply because I feared my world would 'collapse' without that permanence.
In my late 20s, I made a decision that would break me for years. I let go of a partner I thought I truly loved because I was 'losing' myself - my dignity, peace, and values. It was the most courageous thing I could have done: letting go of a path that steered me away from self-actualisation. Knowing my future husband was the only family member I could choose, I wanted a safe space. That meant first letting go. The knowledge that I would inevitably 'lose myself' if I did not exit was the straw that broke the camel's back.
Letting Pain Become My Resolve
Instead of simply marinating in despair, I decided to let pain become my resolve through four intentional pillars:
1) Improving my relationship with short-term pain: To power through the breakup and avoid an on-again, off-again cycle, I started jogging 4-5x a week. I vividly recall the heaviness in my chest as I willed myself through the 3- to 4-kilometre stretch, even on rainy days, despite never having been particularly athletic. I knew I was building the resilience needed to endure the necessary pain of being alone.
2) Overcoming pride for the bigger picture: Up until the breakup, I'd never imagined seeking external help for marriage. I'd always taken pride in being asked out or connecting naturally. However, noticing a pattern of choosing partners who weren't 'marriageable' for me, I opened up to external help. What affirmed this was learning in psychology classes back in university that arranged marriages fared no worse than love marriages a decade later, plus I needed an added reason to not get back with my ex-partner. So, I tried two paid dating services.
3) Embarking on self-healing and discovery: I also embarked on other self-healing and discovery platforms such as, at the time, hypnotherapy and online classes to de-programme my past traumas and enrich myself. Through further self reflections, there was a growing realisation that it wasn't that we were 'bad' people, but that we chose people who were 'bad' for us. As one who aspired toward Maslow's state of 'self-actualisation', I sought a marriage that embedded the conditions for us to both flourish, such as a safe space for emotional honesty, vulnerability, and acceptance.
4) Being courageous and explorative: Being open to love meant being open to failure and heartache. Since I had already overcome the mental hurdle of undergoing paid dating services, I decided to be exploratory on the various social platforms and apps, conversing with and meeting people I would otherwise never have just to 'scratch a curiosity' and inform me of my preferences. As unpleasant as some of these interactions were, they helped shape my marriage decisions later.
The Reality of Paid Dating Services
Paid dating services carried a stigma that they were for 'undesirable' people, especially among young Singaporean millennials. I carried those beliefs strongly. What changed this was the combination of lived experience (having ended three long-term relationships that started more naturally), hearing about some positive experiences, and weighing the odds of finding a partner by myself vs assisted support within a specific timeframe.
Life on these services wasn't easy; it required immense mental effort to get through dates that weren't working.
- First Service: I actually broke down during our first consult, which was soon after my third breakup. The consultant was empathetic and seemed to take a liking to me. She subsequently paired me with a pilot and a corporate high-flyer, among other picks, but the matches were mostly values- and personality-misaligned.
- Second Service: This was a much worse experience. I observed that the quality of matches hinged greatly on the rapport I had built with the consultant and their impression of me. Some dates were so traumatic that I remember turning away from one entirely and calling the agency to say I could not proceed.
Social Platforms & Dating Apps
During 2020-2021, I also used many dating apps such as Tinder, Bumble, and CoffeeMeetsBagel. I became much more exploratory - conversing with people I didn’t usually feel comfortable with - because hey, none of my past relationships had worked out!
I also interacted with people who slid into my social direct messages (DMs) and even dated someone from there for a few months. We explored religious classes together, but eventually parted ways due to different life views. What started out as physical attraction affirmed me that looks alone do not keep people together.
Ultimately, I found my husband on CoffeeMeetsBagel. I was apparently in his explore page and he’d paid 'beans' to talk to me ahead of schedule!
Reflections Through Dejection: Luck vs Effort
At my lowest point, my elder sister asked: "Have you ever wondered if it ultimately comes down to LUCK? Do you want to find your '100%' or do you want to get married by a certain timeline? Because the answers might look very different." That sobered me. Thinking through the people I had been drawn to or marriages I aspired towards, I realised a '100%' might not realistically exist. I drilled down into what I could accept and what I could not, leading to my Personal Criteria List where I looked for someone who met ~85% of the following:
My Factors to Consider: 1. Looks, 2. Financial Fitness, 3. Personality, 4. Education, 5. Health, 6. Personal & Family History, 7. Religion, 8. Ethnicity, 9. Relationship History, 10. Intellect, 11. Values (Non-Negotiable), 12. Emotional Connection/Support, and 13. Gut Feeling
For each of these factors, I had a rough idea of my preference. Under the 'Intellectual' plane, for instance, I was looking for someone who appreciates learning and demonstrates intellectual curiosity. I was thus drawn to my husband on our first date when he shared the latest philosophical book he was reading. There were also factors I did not include in the list, like 'View on Kids' or 'Love Languages', as they weren't important to me or were already represented by extension.
I further drew up a complementary '7 Questions Checklist' - adapted from a YouTube self-help video on romance which I resonated with - to help evaluate compatibility from a more emotional perspective. (I kept a physical list of this in my purse, as a reminder, when I went on dates!)
The '7 Questions' Stress Test:
1. Do you personally find him/her attractive?
2. Is he/she capable of and willing to adapt to your activities?
3. Does he/she help you self-actualise?
4. Is he/she worth it at his/her worst?
5. Is he/she ready for a relationship in his/her current state?
6. Does he/she make you feel emotionally secure across social and life situations?
7. Is he/she respectful of (or aligned with) your spiritual/religious views?
The Silver Lining Of A Longer Journey
There were two things that bothered me most in the search for marriage. First, it was the unavoidable anguish of my third heartbreak. Second, to accept that I had to take a 'longer road' while many Singaporean females were settling down in their late 20s - the exact point at which I was starting over. I don't want to skirt over these, because they were as much my pain as they became my resolve.
I got through my heartbreak by keeping my eye on the 'long game'. A meme I saw on social media perfectly captures its essence: Being single is one step away from a good marriage, but being in a bad relationship is two steps away.
As for the longer journey, I anchored myself in the 'Goldilocks' research on marriage. The research suggests that the ideal age for marriage is between 28 and 32; it balances emotional maturity and life experience with the flexibility to adapt to a partner - avoiding the higher divorce rates of marrying too young (<25) or the slightly increased risks associated with the mid-to-late 30s. Since I was in my late 20s when I broke up, I knew I had a few-year horizon to find my 'one' within that window. For every reason to feel defeated, I looked for evidence to keep my spirits up.
Other Reflections From the Search and 2+ Years of Marriage
Even with intense preparation, I don’t believe we can ever know with absolute certainty who to marry. This is because marriage isn’t a destination, but the start of a long journey between two evolving individuals. Recognising that it's unlikely for anyone to meet '100%' of our criteria required a serious evaluation of trade-offs - a process that, for me, took long periods of reflection and seeking out diverse perspectives.
1. Marriage is a CHOICE we are empowered to make: When presented with the sobering question of finding my '100%' vs marrying by a certain age, I realised my ideal and reality didn't match. I had never encountered a '100%', but I did know I wanted to be married. For context, we might love someone but realise we haven't grown into the same life conclusions yet, or we might love someone who meets only some of our important criteria. This empowers us with a choice: marry with known trade-offs, hold off, or choose a different relationship structure entirely. In my late 20s, I firmly wanted to settle down; that clarity helped me refine my criteria and choose a person I knew I could accept and love.
2. Choosing love means choosing a DYNAMIC: My '7 Questions' checklist was inward-facing because I believed that the choice of partner can shift the entire trajectory of one's life. Hence, a sustainable relationship to me is one where both partners mutually benefit in ways that build toward their self-actualisation. My most painful breakup wasn't because I stopped loving my partner; it was because staying would diverge from my desired path in life.
There is a saying that we are the average of the people we are closest to, and this rings especially true of a life partner. I’ve learned it’s not just about who our partner is, but who we collectively become. As someone seeking peace from my own competitive and anxious energies, I came to appreciate an equanimous partner who valued my zeal. As a 'T' dimension on the MBTI, I couldn't 'run' from reason; I recognised that all my past breakups were rooted in logical long-term incompatibility. I used the forced reflection of Covid and burnout to see myself clearly - my pain points, vulnerabilities, and boundaries. I realised the right relationship should improve, rather than weaken, my relationship with myself.
3. It is important to FRONTLOAD difficult conversations and factor in imperfections: Marriage meets us where we are, not where we hope to be. As much as we strive, we may never be perfect or free from our baggages. I found it useful to be transparent about our imperfections and what we needed early on so they could be factored into the consideration of marriage. For example, I recognised how teenage social rejection shaped my sensitivity to perceived threats; I needed a partner who was deeply affirming and communicative. Conversely, he was transparent about a genetic condition that required us to seek counseling early on. Because of my health-driven lifestyle, we also discussed an adjustment of his habits to assure me of our future together. These weren't one-off talks, but an ongoing dialogue about trade-offs and how we complement each other.
4. Marriage is a societal construct, but how we DESIGN the approach is up to us: Learning about the history of marriage - which allegedly began around 2350 B.C. for property and alliances, rather than love - was deeply freeing. Instead of conforming to established norms about what marriage should look like or our gender roles within it, my husband and I articulated our own expectations. We viewed marriage as a choice based on mutual consent and continual discussion as we evolve, rather than an outdated obligation. As avant-garde as it sounds, we agreed before marrying that we were not 'obliged' for the marriage to last. It is something we hope for and work toward insofar as love and compatibility exist. This is why 'values alignment' was the most important part of my checklist.
5. We can never be 100% certain, but we can take THOUGHT-OUT LEAPS of faith: During marriage education, we were cited high divorce rates of >20% in Singapore and >40% in the States. Rather than feeling dissuaded, I saw these statistics as a reminder that we can never know for certain. Knowing the pitfalls helped set a realistic expectation: this decision is ultimately a leap of faith. When it came time to decide, I leaned on the parameters I had set, knowing this path would lead to the least regret.
Conclusion
My journey towards marriage wasn't a straightforward path. I chose to do things differently even if the outcomes were not guaranteed. While tough, I do not regret this journey because I know it ultimately allowed me to grow.
If there were one takeaway I would like my readers to have from this experience, it is to be courageous in the face of uncertainty for things that truly matter to you. It is to try, especially if the risk of not trying outweigh the risks of doing so. Nothing in life is guaranteed anyway. So, too, marriage and relationships. But what stays with us, regardless, is the journey of growth and striving that ultimately define us and many other challenges we will take on in life.
Life is short and our years so important. So go, live it! <3
Sincerely, Meng Yee
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