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54 dates in 8 months: How this 32-year-old single woman tackled her search for love and romance

By Singapore standards, I was a slightly above-average student, from my PSLE to O Levels, A Levels, and finally, my second-class honours degree.

On the non-academic side of things, I was equally average: Athletics team in primary school, basketball school team in my all-girls secondary school and then treasurer of my junior college’s Photographic Society.

As a working adult, I was doing… averagely fine. As a writer-producer at production house Protagonist by M, I was crafting characters, weaving story arcs and writing scripts based on the ethers of my imagination.

From the ages of 24-30, I was on dating apps. I was on Tinder when it was but a wee flame. I was on Coffee Meets Bagel when it was filled with supposed doctors, lawyers and entrepreneurs. I was on Bumble and tried witty pick-up lines from my own creative vault (but of course, I failed very horribly).

Most of my dates stopped after the decisive three-dates count. The guys I met always gave me the same feedback: You are a great conversationalist over text, but there is no spark in real life.

Stuck in an endless cycle of anticipation and rejection, I found myself dreading the whole process of meeting new people, sharing the same information about myself for the 37,267th time and then feeling disappointed when they stopped replying to my texts.


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At the grand old age of 30, as I stood on the brink of being labelled an evergreen “leftover lady”, I decided to reflect on my experiences with love and dating.

Why is love always seen as something that is organic and natural? Is love always dictated by fate and destiny? Are my unsuccessful attempts at finding the one an indicator of how unlikable I am as a girlfriend, as a romantic partner, and as a person? Am I so unlikeable as a girlfriend?

It was decided that, for practical and ethical reasons, I would be the subject of the social experiment. We would name the documentary Shermin’s March.

It was also decided that the experiment would be given an eight-month-long runway so that it had at least a chance of succeeding. My executive producer, Jeevan Nathan, initially wanted to set a ticking clock – that I walk down the aisle after eight months. Luckily for me, that was deemed unnecessary.

But once the exhilarating tizzy of producing a series so close to my heart had settled, I was made to think about the reason for my participation in this social experiment. Cassandra Chiu, the series’ counsellor, urged me to consider my motivations for doing the series.

Take my first date with “Beethoven”. Not only was he older than what he’d indicated on his profile, in his quest to share his experiences as a maestro, he spoke till the lights at the park came on in the evening – a good two hours. That was our first and last date.

Then there were the ghosts – men who seemed to disappear right on the day of the date.

Of course, there were also rather enjoyable dates, but the majority of these reached their conclusion after three dates. And I am thankful that these dates ended when they did, cause you know, sunk-cost fallacy and all.

In this journey to find The One, my views on men, romantic relationships and happiness have shifted considerably. I began to understand the unsaid stereotypes that we have of men and women when it comes to love and romance, and also, the realities of dating.

Hollywood rom-coms and Korean idol dramas paint a highly unrealistic version of what love is. We are human beings with flaws and acne, it is exhausting to expect our dates to be as charming and romantic all the time.

More importantly, I also discovered that I have the strength and tenacity to pick myself up from bad situationships and move on. I have done what I hope my characters do: Develop positive character traits and values to deal with the lows of life. Not bad for quite an average person.

Catch Shermin’s March on CNA or on CNA Insider’s YouTube channel on Oct 14-15.

CNA Women is a section on CNA Lifestyle that seeks to inform, empower and inspire the modern woman. If you have women-related news, issues and ideas to share with us, email CNAWomen [at]

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