The Singleporean: Finding courage in heartbreak

The Singleporean is an anonymous column by a 30something, female Singaporean writer who’s obviously single (and cautiously ready to mingle). She pens her thoughts on work, relationships, and adulting from the lens of a millennial on the cusp of a mid-life crisis.

We all know the rule: Never pursue a romantic hookup with a friend unless you’re prepared to rewrite the dynamics of your relationship.

A few months ago, I tossed this playbook aside when I decided to revisit a connection I’d made on Bumble while on holiday in Stockholm last year. It wasn’t meant to be; we were both living very different lifestyles in distant cities – there were simply too many hurdles for two people who had just met on a dating app. So, we kept in touch as friends.

In July, eager to experience the Scandinavian summer – and to put as much distance as possible between myself and work – I returned to Stockholm for a second visit. We spent a few hours catching up at a cosy pizzeria, and he offered to show me his favourite spots in the city.

Battling jet lag and the truth-serum effect of wine, I confessed a deeply held regret: If not for the distance between us, I would have liked to see how our friendship might have developed. That seemed to hit him like a bus – which, of course, did wonders for my self-esteem.

After what felt like an awkward pause, the conversation shifted into a debate on the pros and cons of giving in to our attraction. By the time he walked me back to my hotel, it was 1am, and I was ready to put the night – or morning – behind me.

Heartache is unavoidable

Being the stubborn Aries that I am, I couldn’t resist bringing it up again two days later, while we were basking in the sun by a lake. He let out a long, weary sigh (I tend to have that effect on people) and asked, “What is it that you’re looking for? I really don’t want anyone to get hurt.”

“Nothing – it ends when I leave,” I replied, surprised and feeling vulnerable at the truth of my answer. I had no illusions about this situation working out in the long run, but at that moment, I was certain it was worth the impending heartache.

“Okay,” he said as I gazed down at our feet in the water. The tension was palpable. He leaned towards me, and we kissed. We spent the rest of my stay exploring our chemistry together.

When we said goodbye the night before I left, I felt a pang of sadness. Despite the fleeting nature of our fling, the intimacy we shared offered a glimpse of what might have been. “If you were based here, we would have gone out more,” he added.

Moving forward and letting go

A few months later, we’re now on an unspoken hiatus – it’s hard to ignore the emotional attachment that formed. Will we meet or speak again? I don’t know. It’s a sobering lesson: In following my heart, I might have risked losing a friendship for good.

Yet the spontaneity of a summer romance taught me to trust my decisions, set clear expectations, and find the courage to move forward when it’s time to let go.

I might be foolhardy, but when I’m staring at the bottom of a glass, I’d like it to be half-full – preferably with a double shot of tequila.

Have a topic you’d like us to explore? Email your suggestions to magherworld@sph.com.sg with ‘The Singleporean’ in the header.