As a kid, I had certain preconceived notions about how my life would be as a grownup: by a particular age, I’d be in a relationship and by another age, I would be married. I imagined romantic love to be unconditional, and I wanted someone who would be happy for me no matter what. 

It was only last September, a few weeks after my 26th birthday, that I started dating someone who would eventually become my first boyfriend. As someone who started dating in her 20s, it was a long process to get to where I am now but I’m glad that I’m having my first relationship later than most of my peers. I’m way more mature now than I was as a 20-year-old.

I started dipping my toes into the dating scene by downloading Tinder. A lot of friends were already in relationships or had been dating for a while, yet I hadn’t experienced any of that. 

In the back of my mind, it was frustrating to wonder why I was single and to imagine that no one would love me the way others loved my friends. 

Hearing me lament about it, a friend suggested that I wasn’t putting myself out there enough. Being super introverted, dating apps seemed like the least stressful approach to dating. So I downloaded Tinder. 

I’ve been in situations where a friend tells someone on my behalf, “My friend thinks you’re cute”, or where friends plot to set me up on a blind date, but these situations felt more stressful and agonising.

I don’t think my issue was not putting myself out there enough but developing self-awareness of knowing who I am and who I might be compatible with. It also partly comes down to luck.

You can’t really control luck but you can try to maximise your chances of meeting the right person by getting to know more people, so I continued to swipe right. In the last five or so years, I’ve probably deleted and downloaded Tinder over 10 times. 

I’d go through the whole, “There is nothing here for me. I’m not going to waste my time.” Then a month later, I would say, “Okay, I’m ready to try again.” I’m an intense overthinker, which is why I found dating so stressful. Before meeting someone, I’d worry: are we going to hit it off, are we going to have a good conversation, or is he just going to want to talk about my work? 

I kept my bio pretty short — consisting of one lone emoji, because I was self-conscious people might recognise me, take screenshots, and say something mean. Having such a public social media presence, I’ve been bullied before and I know how bad that feels. Out of precaution, I wanted to keep my profile vague enough that if anything goes viral, I can pretend that it isn’t actually me. 

I don’t want to pretend that my work isn’t interesting, because I love what I do for a living. I also imagine that I would be excited to meet a personality who I’ve been following online. But when I’m dating, I don’t necessarily want to be talking about my work all the time. 

It makes me second guess why they matched me at all, and it became extra draining trying to filter out people who weren’t genuinely interested in dating me.

Feeling really jaded that there seemed to be more people interested in seeing who I was for being Preetipls than anything else, I paid for the premium account Tinder Gold to see who exactly already swiped right on me. It was overwhelming to see that there were thousands of profiles awaiting me to go through, but I enjoyed having the option of being able to see who liked me first instead of mindlessly swiping on everyone on the app. It was less anxiety-inducing – I could avoid getting my hopes up and waiting around to see if someone might like me back. 

Dating can entail a lot of ambiguity because not everyone is interested in exclusivity or settling down. Since I am, I learned to be clearer about it to avoid wasting time and crossing wires with someone else. Usually if we meet on dating apps, I’d ask what the other person is looking for over messages online. Otherwise I’d try to observe how present and invested they are during dates and about two or three dates in, I’d ask what they’re hoping to get out of our situation or what they see me as. 

There was someone who I thought was only seeing me because we spent Valentine’s Day together, but I found out from friends that he was dating around. When my dad was warded in the intensive care unit, I told him what a hard time it was for me. He didn’t reply to my message for four days and by the time that he did, my dad had passed away. It hit me that I couldn’t be with someone who’s scared to be there for me when the going gets tough. 

This is my life, and I don’t necessarily need you to know the right things to say but I’d appreciate it if you could just be there and listen. If you can’t even do that then it’s a red flag. 

But at least dating is not such a far-fetched endeavour that it’s difficult to find friends to commiserate with. With single friends especially, we would confide in each other who we’re talking to, what sort of guy troubles we’re facing, and we would keep each other motivated. 

There were also days when I felt so horrible and bogged down by negativity that I just wanted to be on my own, so I dialled back on dating and going out with friends. It could take a lot of convincing to tell myself that my life is not over just because I haven’t found love like others have. But it was through giving myself this personal space, sitting alone with my thoughts and emotions, that I learned to be at peace with my singlehood. 

I remember watching the Miss Americana documentary in which Taylor Swift said that although millions of people watch her on stage, she feels alone once she’s home. Because there’s no one to share the joy with after it all. That really resonated with me. I craved having a person with whom I could celebrate the small wins in life with, like having someone to text after completing a video that I’m proud of. I knew I had my family and friends but it just wasn’t the same. 

It took dating over the years and being on my own for me to realise that I never needed to have a partner, I just wanted it. I wanted to feel a certain way and wanted to have a special someone in my life. 

When I first started dating, I thought I was looking for the perfect someone, and this placed a lot of pressure on my search. It probably would have also placed a lot of pressure on the person I’m with, knowing that their behaviour will affect my mood 24/7. 

I always thought of myself as grown up and independent, because from young, I watched my parents separate and my family overcome financial struggles. But I think actual maturity and readiness for a relationship only kicked in when I could rationally see that my person shouldn’t be my everything but one of the amazing things going on in my life. And this only came about from sitting alone with my thoughts. 

I asked myself questions like what am I satisfied with and why do I feel like what I have is not enough? After questioning myself over and over, I guess it hit me that what I have — a job that I love and supportive people around me — is enough. And I think that’s what made me finally ready to be in a relationship.

So if you’re single and looking for a relationship, I would say not to rush into anything for the sake of it — don’t do it because you feel pressured by friends who are attached or think that you have to settle with someone you’re not entirely into because they’re the best you’re going to get.

Relationship factors like timing and having someone else interested in you can feel so out of your control, but I think it’s important to first focus on why you want to be in a relationship and what you’re looking for in a partner.

I went on my first one-on-one date with my boyfriend during a time when I wasn’t looking at all. Last September was a rollercoaster of emotions for me. I was in a weird place because I lost my dad. It was also my birthday month and it felt like I had to put up a front despite not being in the mood to celebrate, because my family could use something to look forward to. 

When he heard about my dad’s passing that very month, my boyfriend — then more of an acquaintance, texted to suggest that we grab a drink. He recently lost his dad as well, so he could understand what I was going through. He’s someone who I first matched with on Tinder in 2017. Over the next three years, we matched another two times on Bumble and on Tinder again, but we never made solid plans to meet up. We were just in different phases in our lives. I was actively dating but on dating apps, you meet so many different people; and for a while, he got together with someone else.

It’s only now that I look back, I realised my boyfriend and I had some pretty deep conversations, even through our brief correspondence online or when we bumped into each other out in public.

In the midst of one of our first few exchanges in 2017, my dad called saying that he had cancer, so I mentioned it. It might seem like a lot to share with someone you’re just getting to know but it was comforting to have him to talk to.

We clicked so easily and I think this is partly thanks to a similar family background and upbringing. With other guys, there would be a bit of a disconnect whenever I spoke about struggles going on at home. It was as if they couldn’t relate or didn’t know how to respond.

On our first date, he said, “I’m going to just put it out there that I didn’t know what to expect when I came here, but I didn’t expect it to go as well as it’s going.” I said the same, and he continued, “I don’t know if you feel the same way but I’d really like to see you again and go on a second date.” 

I felt a huge sense of relief because here was someone not playing mind games and just saying how he felt. The night ended with him asking if he could hug me before we got into the cab. I thought, wow, I have been on enough dates to know that this is not normal behaviour. We’re comfortable enough to let each other know how we really feel, even if it’s a “Wait, are we moving too fast?” 

Four months later, in January, he asked me if I could be his girlfriend. I’ve been single for so long that things like introducing him to family and friends feels like a foreign concept. I met a bunch of people for the first time and made them laugh with a joke, then said it’s actually my partner’s joke. It was so weird to feel the word “partner” roll off the tip of my tongue. I’m feeling all these new emotions that I never realised I was capable of. It’s new, it’s exciting, but I also definitely feel very secure. 

Photos provided by Preeti Nair.

This is the third part of our four-part Valentine’s Day series The Things We Do For Love. Click here for the first and second stories. Stay tuned for part four, which will be uploaded next week. 

Writer’s Note:

My name is I Yune, and you can find me at @i_yune on the Dayre app. On my personal account, I've previously written about being happily single from when I was 19 to 28 years old and meeting my boyfriend on Coffee Meets Bagel.

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