I Remarried At 50, To Someone I’d Known For 30 Years

When my first marriage ended in 2023, dating was the last thing on my mind.

The divorce was acrimonious and complicated, especially where custody of our children was concerned. Much of my attention and energy went into legal processes and negotiations, and in the midst of it, I found myself withdrawing from the world. I accepted that I might raise my children on my own, and that’d be perfectly fine with me. 

A marriage that ran its course

My ex and I got married in 2002 in Hong Kong. We built our lives there together and had two children. Our daughter is now 19 and our son is 10. 

Over time, the marriage became increasingly difficult. We had different views on life and how we wanted to bring up our children. We tried counselling but eventually had to admit that despite our efforts, we weren’t able to move forward together.

We returned to Singapore in 2020 during the pandemic, still married even though the relationship was gradually unravelling. In May 2023, I filed for divorce.

I was living with my mother during that challenging time and bumped into my old polytechnic classmate R nearby. We had a simple 15-minute conversation. It felt comforting to reconnect with a friend after having isolated myself for a while.

A familiar face at the right time

R and I knew each other from the same visual communications course back in the 90s. We had known each other for 30 years, staying loosely connected on social media.

We had fun times in school. I always saw him as a younger brother as he’s four years younger — I joined the cohort later. I was even his “wingwoman” once, attempting to set him up with one of my friends though it didn’t work out. We still joke about it now.

A few months after our chance encounter, we met up for coffee where we caught up on each other’s lives and spoke about our former classmates. The conversation flowed easily and was entirely platonic. Like me, he is a lecturer and divorcee — his relationship ended years earlier and they didn’t have children.

After that, we texted each other from time to time. He invited me and my daughter to church for a Christmas show — my son was with my ex in Hong Kong at the time. I started joining him at church after that, and we got to hang out more at group gatherings. 

He seemed like a really caring guy, but I wasn’t sure what to make of it. He was always there when I was stressing out about my kids and would come over to check on me. Surely, he wasn’t just being friendly?

After my divorce papers were signed, I decided to clarify things instead of guessing. Over text, I asked him directly if he was just being nice or if he liked me. We are both people who don’t play mind games. He confessed his feelings for me and we texted late into the night. 

From the start, our relationship didn’t feel like a dramatic shift. I simply felt safe with him, but it was funny how long it took for us to decide we were right for each other.

Fitting together pieces of a puzzle

It was awkward at first, transitioning from friends to a couple. After all, we were never each other’s type. He used to like taller women (I’m only 161cm) and I never dated younger men. 

I was also plagued with insecurities. He was an eligible bachelor who would be able to build a life with a partner without kids or emotional baggage. By being with me, it’s like he inherited a burden. Perhaps he had a saviour complex, I thought at one point. But I don’t let these worries consume me, because there’s also no denying how compatible we are with each other.

We have many common interests. We like board games and movies (especially sci-fi, superhero and anything quirky) and even attend design conferences together for fun. It can be uncanny how in sync we are with each other. Once, we decided to watch a movie on Netflix and texted each other our top choice at the same time — it turned out to be the same title.

What also draws me to R is how he’s comfortable being the “fun uncle” to my children. He’s self-assured enough to know he would never replace their father. He is simply a supportive presence who understands that the well-being of my children is my top priority. 

Before proposing to me, he even asked my daughter for her blessing. My teenager gave him a high five as a sign of approval.

We got married in November 2025. I was 50 years young, enjoying our wedding at Chijmes, a dream venue since my 20s. More than 180 people turned up, including family, friends, former classmates and lecturers. It was warm and joyful.

How divorce has shaped our second marriage

As divorcees, R and I both understand that marriage takes work. Shared interests help but they don’t guarantee anything.

There’s also emotional maturity that comes with our experience. We know the importance of being honest with our opinions. While we disagree on things now and then, we talk it out calmly. 

I don’t want to compare my ex with R, as I am still thankful for the good times we had in my first marriage. As old friends, R and I simply hit it off and decided to give “us” a try. 

Home is now an executive condominium we share with my daughter. We have filled our place with art and photographs by our friends, and had fun renovating the place — we have similar taste in design. 

Our goal now is simple: focus on our kids and our work to provide security and stability to our lives. It may not be romantic, but what we have is grounded. What we have is love.