Sex & Love

What she's truly thinking: A serial first-dater at 29 who's seeking her Happily Ever After

Having sat through one too many first dates that go nowhere, I begin to wonder where the problem could lie

first date

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In the 2016 rom-com How to Be Single, Alice Kepley (played by Dakota Johnson) mused, “The time we have to be single, is really the time we have to get good at being alone. But how good at being alone do we really want to be? Isn’t there a danger that you’ll get so good at being single, so set in your ways that you’ll miss out on the chance to be with somebody great?”

I won’t lie. That moment hit me hard.

I’m an incorrigible first-dater who hasn’t gone on a second date for more than a year. Crushes? Sure, I’ve had a fair amount over the years. And I’ve had no shortage of suitors. But at 29, I have never had a boyfriend or experienced falling in love.

So the movie triggered several questions that I wasn’t comfortable answering. Was I really becoming too good at being single? Was I afraid of committing to a relationship? Was I short-changing myself by not venturing out and taking a chance on someone – anyone?

forever alone

Photo: Gifer

And, more importantly, was I just running away from the overwhelming fear of letting someone into my bubble, laying out all my flaws and vulnerabilities for them to judge?


Is there really a soulmate for everyone?

The notion of soulmates presupposes that there is someone for everyone. It’s a romantic ideal: there aren’t plenty of fish in the sea, but truly, one perfect fish person out there waiting for our bait.

And it’s an ideal I had bought into. I would embark on a date expecting to meet my soulmate, believing that all I needed to do was look harder, sit through more insipid dates, before finally meeting a Mr Right on my final, momentous, fateful first date.

But to arrive at that point, I needed to first figure out what that Mr Right looked like, what he embodied, and why, exactly, he was right for me.

mr right

Photo: Giphy

My criteria were arbitrary – I went for the “vibe” instead of anything concrete, which often led me to create my own illusions of the guy instead of getting to know what was right in front of me. Not the best way to meet my soulmate, I realised.

“To be soulmates with someone, you need to first bare your soul,” said another friend of mine who married her childhood sweetheart.

It sounded simple in theory. In practice? Not so much, at least for me, a walking bag of neuroses and anxiety who finds the idea of opening up to anyone terrifying.

It always boggled me how couples realised they were made for each other. How could they be so certain? How did two souls grow close enough to become a part of each other? For someone who could barely get a second date, finding my soulmate seemed more like a myth than a goal.


Comfortable being alone or lonely being comfortable?

I am more comfortable being alone. Who needs the added pressure of dressing up and holding civil – engaging – conversation with a stranger when you can just Netflix?

But it soon started to seem like a convenient excuse to hide from that pressure of not living up to someone’s expectations, of creating that spark with a near stranger.

darcy shy

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“You’re pretty and smart and nice,” more than one friend has remarked. “Why is it that you’ve always been single?”

Maybe I could be a catch. But a university degree, photogenic looks, and a figure toned from swimming and yoga weren’t enough to sustain a connection beyond three dates, tops. It felt easier to be alone. Solitude was good. Solitude was simple. Uncomplicated. If I didn’t care about someone else, I wouldn’t have to put myself in a position where I could get hurt.

And, according to a particularly astute friend of mine, I am “the sort who would always get hurt in a relationship”.

“You’re too non-confrontational. That’s not how a good relationship works,” she said.

She was on to something there. As a conflict-avoidant Libra, I cared too much, hurt easily, swallowed my pain and pretended everything was fine. I didn’t like upsetting people, even if it meant I had to put aside my feelings just to make them happy. An offhand, negative remark from them could send me spiralling into anxiety, wondering if I did something to displease them.

chandler bing needs love

Photo: Giphy

It was just easier to not get involved with anyone at all, if only to spare myself the inevitable angst and frustration that came with the cotton candy moments.

So I had always kept people at arm’s length, coasting by on first dates (and the odd second or third) and then parting ways just before things got serious or complicated. A well-guarded heart cannot be hurt, after all.

In the 2009 rom-com, The Proposal, Margaret Tate (played by Sandra Bullock) declared, “There’s a reason I’ve been alone all this time. I’m comfortable that way.”

comfortable being alone

Photo: Giphy

And I was relieved. Someone – albeit fictional – felt the same way as I did. My singlehood was validated. Really, it was because we chose to be that way, not because we were afraid of being with someone.