Seeking Connections, Finding Clarity on OkCupid in Singapore

What is it like for a hopeless romantic to grow up in an age where online courtship is the standard, and the site of your meet-cute is most likely a dating app? A 22-year-old Singaporean girl — who is no stranger to “swiping” having done so intermittently over the course of five years — shares her online dating encounters and explains why she has a soft spot for OkCupid.

I have always been and will always be a hopeless romantic; I spent the bulk of my teenage years fixating on fictional relationships in romantic comedies and novels (shoutout to Percy and Annabeth from the Percy Jackson series). My naivety also led me to believe that as long as I treated others well, they would return the favor. Unfortunately, this was not the case and my partners often wound up disappointing me. Yet, I still continue to have high expectations when it comes to finding a life partner — I’m not willing to settle for less than what I want.

These days, the easiest way to meet people is through dating apps. But what happens when a picky girl with a tendency to idealize romantic pursuits is granted access to endless choices? Well, I was initially overwhelmed but eventually narrowed my search by primarily sticking with a platform that prioritizes users’ understanding of one another, and OkCupid did just that.


My first foray into online dating was in 2016, back when I was a first-year polytechnic student. After receiving encouragement from a friend who met his then-girlfriend on Tinder, I delved head-first into the abyss of dating apps. Since then, I have forged numerous connections, both superficial and intimate alike, through these platforms. It was how I met my first love; we entered a long-distance relationship that lasted for eight months. While dipping my toes into the uncertain waters to figure out my sexuality, I matched with a girl on OkCupid. I ignored her and eventually only replied after we matched on Tinder. That was three years ago and she has remained an important presence in my life ever since.

Of course, there were experiences that left more to be desired too. Let me tell you about the time I matched with someone who was obsessed with pointing out the two lumps of fat on my torso. Or the time I went on three dates with someone, only to ghost him upon realizing that he was racist, xenophobic and homophobic after a five-hour long video call. I’ve been ghosted too. During the first half of the Circuit Breaker, I was faced with radio silence two weeks after a pleasant movie date (via Netflix Party) with an aspiring musician. Also, if I were to take a shot every time I’m invited to partake in a threesome because I stated that I am “bi-curious” on my bio, I’d be drunk for days. But overall, I chose to stick with online dating because it has given me a chance to review how I seek connections with people — I learned to identify my deal breakers as well as internalized stereotypes, and am better equipped to manage my expectations in love.

OkCupid: A Cut Above the Rest

Although OkCupid only popped on my radar between late 2017 and early 2018, it has set itself apart from the other dating platforms in some ways. Touted as a more “serious” version of Tinder, it has clear categories for the user to indicate whether they are looking for friends, short-term dating, long-term dating or hookups. It also has more inclusive options when it comes to sexual orientation and gender identity labels. Most prominently, the platform has broad categories of “Match Questions” that encourage you to (over)share your values, ideas and thoughts. This helps to satiate my intellectual curiosity and need for emotional fulfilment, recalibrating how I view connections on dating applications. Or maybe, I merely enjoy the thrill of expressing my views — which represent who I am — without feeling the pressure to have the “right” answers.

On my profile, I include categories which contain various prompts such as aspirations, talents, traits, needs and hobbies. There are more to pick from but it really is up to you. You can pretty much list your entire resume on there and it will be socially acceptable. OkCupid prides itself on finding you a match using an algorithm supercharged by users answering questions about themselves. The more you answer, the more accurate the percentage of compatibility between users will be. 

While I have restarted my profile multiple times during my attempts to detox from dating apps (a self-deceptive hoax), I have had my current one for more than a year. I’ve answered just shy of 900 questions, often in a slump caused by procrastination. Those concerning my sexual preferences have elicited more responses than any other type of questions. Most importantly, “Match Questions” help to filter out people who embody different values from me, ones that I deem deal breakers. For example, I would not continue to pursue someone who agrees to a question like, “Are traditional gender roles important in a romantic relationship?” or disagrees to a question like, “Do you acknowledge the gender spectrum?” While spending time scanning through answers may seem like a colossal waste of effort, I prize quality over quantity when it comes to matches. Placing “Match Questions” at the forefront of the experience puts a focus on our beliefs, values and who we are as individuals, reducing the pressure to showcase our best sides through photos.

Many conversations on OkCupid gave me a glimpse of what lies behind the façades many people put up; the most poignant moments I’ve had on the app are when I unwittingly unravel the layers of the person I’m speaking to. Some people manage to act detached during our initial interactions and yet wind up being vulnerable, which always comes as a surprise. I wound up caring for some people from afar as they moved onto better prospects; I learned to let go of others for fear of being rejected. But I was willing to do so for the possibility of finding the right connection. Intimacy is a drug I can’t get enough of, after all. And I love it when strangers talk about their first impressions of me or reveal themselves through something as simple as sharing their thoughts and feelings about their favourite songs.


About half of my friends have found their significant others through dating apps but the thought of finding a life partner this way remains surreal to me. There’s no question that online dating is the most efficient way to form connections in our modern age, especially when there are fewer opportunities to socialize during a global pandemic. In fact, it is sobering to reflect on how my romantic encounters can all be attributed to dating apps alone, given that they have commodified dating and encourage us to self-commodify

Still, I’m excited to see how these platforms continue to shape modern dating and our experiences. While OkCupid is only one of many apps — I’ve also tried Coffee Meets Bagel, Bumble, Tinder, Happn (for only a day) and Hinge — that promise to be designed for deletion, I genuinely think it’s the best. OkCupid has given me the chance to nitpick in ways that I am not able to do so elsewhere; I am now more discerning in choosing the kind of connections I deem worthy of my energy. My journey on dating apps has been many years in the making and I don’t foresee it ending anytime soon. Still, I’ll keep my faith in the process and continue to explore my options mindfully. Where better to do so than on OkCupid, an app that aligns with my intentions and interests?

Feature image by Sherryl Cheong

For more articles like this, check out our Modern Love/Loneliness column.

a contributor

One of many contributors sharing their stories under the cloak of anonymity.

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