Skip to main content



Gen Y Speaks: I'm 27 and I've never had a girlfriend despite dating actively. Here's how I stay hopeful at meeting The One

For some time now, finding a partner and getting married has been on my mind.

The author sees the experience of dating as an important part of growth, helping him know what he seeks in a partner and how to correct the failings he has.

The author sees the experience of dating as an important part of growth, helping him know what he seeks in a partner and how to correct the failings he has.

Follow us on TikTok and Instagram, and join our Telegram channel for the latest updates.

For some time now, finding a partner and getting married has been on my mind.

You might laugh, but for the past 27 years of my life, I’ve never had a girlfriend. Not one.

I didn’t think it’d be this hard. I had thought that running a business, pumping iron in the gym everyday, and volunteering to serve the needy would have made me an ideal bachelor.

Turns out that wasn’t the case.

I had two sources of dates.

From July 2022, I went for some networking events that required in-person attendance. If I hit it off with someone during the conversation, I would ask them if they wanted to go on a date with me.

This may have sounded desperate in a Singaporean context, but I thought: “Well, there’s nothing to lose. If they said no, I would never see them again anyway.”

Three out of five people I approached gave me their numbers.

Then in October 2022, I tried the dating app Coffee Meets Bagel as an experiment. For two weeks, I matched with (almost) everyone the app served. 

They say beggars can’t be choosers, so I tried my best to match with everyone.

I got three dates from there.

I stopped after two weeks because being alerted about new matches everyday distracted me from focusing on the dates that I had lined up.

That’s a total of six potential partners — three from in-person events, and three from the dating app.

But none of them proceeded to what they call the “exclusive dating” stage, the phase when two people are only seriously seeing each other and no one else.

Basically, I was dating, but I wasn’t getting attached. Was something wrong with me?


In order to go on a romantic date, I first had to nail down an actual chronological date. 

But this process can be anything but romantic. I remember one lady whom I met over a dating app, sending me a copy of her online calendar to pick out an available slot.

It felt like I was booking a doctor’s appointment.

Perhaps what was missing here was the spontaneity of meeting someone organically, whether in school, at the workplace, or in the course of doing some activity together.

With these sort of networking events and dating applications, gone are the unrushed interactions that allowed people to find a serendipitous spark.

When we met for the date, it felt like we both had to put on a performance.

It almost seemed like an interview, where both of us were trying to see if we were the right fit for each other.

In this instance, it was my fault for being a picky dating partner. I took an approach in which if I felt she wasn’t interesting enough, I wouldn’t arrange the next.

But looking back, perhaps this was extremely unforgiving of me. Was it really possible to say that someone wasn’t for you after an hour?

It almost felt like I was setting us up for failure.


Desiring a change, I moved on from using dating apps, and paid S$540 to a blind dating agency to help me meet dates.

But finding a person to date is just one brief aspect of the chase. 

I underestimated how much time, effort and energy it takes to nurture that spark. I didn’t think that finding a girlfriend would take this much headspace. 

For one, I quickly realised that I was out of touch with many of my dates who preferred to text. Using WhatsApp or Telegram to nurture a relationship was something which I couldn’t grasp.

I’m that sort of bloke who only sends texts to confirm the time, place, and agenda of meetings.

After all, why do that when it is so much more efficient to meet, have quality time, and build a relationship from there?

It wasn’t that I didn’t want to text, but the fact that after a long day at work, I found it difficult to sit down in front of my phone, look at the text, and try to think of something witty and funny to say.

It felt like replying to an email at work.

In hindsight, maybe I could have put in more effort to go to texting classes and learn to communicate better.

Female friends tell me that texting is a way to figure out if the guy throws up any red flags before the meeting.

They say that it is not the quantity of text messages that made a difference. Rather, it was whether these text messages exuded empathy, love and care.

According to research published in the Journal of Couple and Relationship Therapy, which surveyed 276 men and women in their early 20s, partners who sent caring and loving messages to their dates reported greater fulfilment than those who did not.

Perhaps that was stating the obvious, but it had not occurred to me that communication, even when it is in the form of short text messages, is key to strong relationships.

At this stage in my life, I was trying to move around many big pieces of my life in the first few years after graduating from university. I was figuring out if I was in the right career, thinking of moving out from home, and contemplating shifting from my faith community.

So when I kept trying to find a partner, I was not prepared to put in the work.

And so, I’ve accepted that being uncommunicative with my dates was another failure on my part.


I still haven’t gotten a girlfriend.

Yet as I reflect on my journey so far, a few lessons come to mind.

What if being “ready” for dates is impossible?

There’s a school of thought that says that you should work on yourself, before finding dates.

But after my recent experiences in the dating scene, I don’t think there’s ever a right time to be the perfect partner for that special someone.

Instead, I see the experience of dating as an important part of growth, helping me know what I seek in a partner and how to correct the failings I have.

It is also about knowing how to pick yourself up to try again.

In April 2023, when I was window shopping, I had a conversation with a shop assistant. She was funny, clever, and insightful.

When another shopper came in, I took a deep breath and asked her for her number.

There was a pause. Then she said: “I already have a partner, but you’re always welcome to come by to chat”.

That rejection hurt, although it shouldn’t have. It was nothing against me. She was attached, and didn’t want to lead me on.

But somehow, I was left hurting from that incident for a few days.

The bitterness reminded me of the many times I had been rejected not just by potential dates, but also in school, in job applications, and elsewhere.

Rejections hurt especially when they go against our fundamental desires, and makes us question what is wrong with ourselves.

But I think there’s truth in the Japanese proverb “fall down seven times, rise eight.”

I wish there was a better answer than to just try again. But there isn’t. 

Because finding success in love isn’t just about giving dates another chance. 

Yes, it’s about taking the effort to know them through text, even when you think that it feels like a waste of time. Yes, it’s about being patient, even when the date doesn’t seem ready to progress. 

But maybe, it’s also about giving yourself another chance, to keep dating, even when you’re losing hope.


John Lim speaks on creating happier workplaces for millennials and is the author of the book Vault: Every Gen Z’s Guide to Getting Through the Swap of Adulting. He blogs at

Related topics


Read more of the latest in



Stay in the know. Anytime. Anywhere.

Subscribe to get daily news updates, insights and must reads delivered straight to your inbox.

By clicking subscribe, I agree for my personal data to be used to send me TODAY newsletters, promotional offers and for research and analysis.