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Confessions of a serial dater

How dating apps make you want to stay single
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Content warning: This article contains descriptions of sexual assault. 

I met my ex on Tinder in 2017 when I was a bright-eyed 18-year-old in my first year of university. 

He is the first and only person I’ve ever loved romantically. Before lockdown, we were spending nearly every waking moment together. I grew up with him. I saw him buy his first car and experienced my first overseas vacation without my family with him. I wasn’t sure who I was without him — and the lockdowns spent in solitude within my strict Asian household had forced me to confront this reality. 

We spent two and a half years together — he was my first serious relationship and the person I’d considered to be my first love. But three months into lockdown, I made the decision to end things. I loved him tremendously, but I realized I couldn’t see a future with him.

As this past September came to a close, there I was, having just entered my fifth and final year of university in my new apartment. I decided it was time to put myself out there again. And when I decided to go back on dating apps, I set the intention of dating casually. 

After all, I had spent half my undergraduate degree highly dependent on one person. I knew right away that I wanted to meet many different people. I thought, hopefully, after meeting these people, I could figure out what I would like and dislike in a future relationship. After exploring my options, I could have a successful long-term relationship in the future without wondering if there was anyone out there who could possibly be better for me.  

The popular choice of dating apps had changed since my first year of university. Back in 2017, Tinder was the go-to dating app and Bumble was still rising up the ranks. A year into my relationship with my ex-boyfriend, I had started to hear my friends talk about Hinge. They told me about how the app’s purpose is to be deleted, as it was created to foster serious relationships. 

Of course, in support of my personal belief that dating apps that make such bold claims are destined to fail, the app was never deleted from my friends’ phones. Instead of stable, long-term relationships, the dating app had left them with strange and funny first date stories that we gushed about over several glasses of wine. 

I turned my friends’ dating stories into a challenge. Truthfully, I picked up online dating like I did writing and painting — it developed into a bit of a hobby.

The start of something new

One of the first guys I started seeing in the fall was actually someone I’d met before on Tinder. He reached out to me on Instagram after seeing me on Bumble. I met him for the first time shortly before meeting my ex-boyfriend and ghosted him shortly after. 

Meeting him again brought back the same feelings I had when I met him four years ago — I felt comfortable with him right away. On our first date four years ago, he had been an outgoing and quirky third-year engineering student. He’s now working as a consultant at a tech company and hopes to move to San Francisco in a year to work at the company’s headquarters.

Currently, my ‘type’ consists of men in their mid- to late-twenties who are eager to show off their successful careers and talk about their past or upcoming travels. Given the kind of men I am interested in, I consider most of my dates to be a form of networking coupled with free dinners and sex. This man, who I refer to affectionately as “consultant guy”, has turned into a more or less consistent friend with benefits. As someone who works 12-hour days and frequently works on the weekend, I don’t see him very often — but like clockwork, he almost always messages me on the first Sunday of each month. He always buys us dessert afterwards and jokes that he has a “second stomach” for dessert. 

He’s somewhat positioned himself as my mentor, helping me weigh the options on a future career. Beyond that, he also has an insatiable hunger for adventure, a great sense of humour and seems to exude joy wherever he goes. However, it’s clear every time we talk that we have vastly different opinions on life. Regardless, I value his opinions and time, and it’s obvious to me that he feels the same.

Recently, I went on a first date with a sweet 27-year-old realtor. Despite the four-year age gap, I noticed that we have similar outlooks on life, especially in regard to work, family, and dating. He felt much closer in age to me than the consultant guy. On our first date, he asked me how many dates I’ve been on and about what brought me to Hinge. We shared similar reasons, and, over drinks, we quickly discovered just how much we had in common. 

We spoke almost all night, and the night seemed to last forever, in the best way possible. We shared book recommendations, listened to music together, and bonded over our favourite movies, both of which star Ryan Reynolds. 

I went to his place at 8:30 pm and left his place at 12:30 pm the next day. He promised to lend me the book that changed his life next time we meet, and to take me out to his favourite bars once they reopen.

Other dates I’ve met since I’ve moved out of my parents’ house have included a 24-year-old working in sales, who I bonded with over our love for skating, and a UX researcher who, coincidentally, grew up in the neighbourhood in which I spent most of my childhood. 

Not your manic pixie dream girl

Despite my interest in casual dating and reluctance to jump into a committed relationship, my experiences with online dating have left me with mixed feelings. Sometimes I’m left with a lingering sense of ‘what if?’ as if part of me wants more from a date. Sometimes I feel like I could be a great partner to the men I’ve met, give or take one or two things. Most of the time, it all boils down to timing. 

I’ve noticed that going on dates has amplified my anxious tendencies. I find myself overthinking our interactions, wondering why they haven’t texted or called in a while. I often feel as if I’m treated as a manic pixie dream girl whose only purpose is to reassure men and encourage them to keep going. 

With each of these dates, I feel a false sense of security and emotional intimacy. We’ve felt comfortable enough to open up to each other about our hopes and dreams for the future, and to talk through deep-rooted insecurities about our past relationships. I’ve never been one to get that infatuated after the first date — but, sometimes, it can be hard to detach. I’m still trying to reconcile the fact that I can share intimate moments with someone and still have a relationship primarily based on reciprocal exchange.

As much as many of these men have left me with meaningful conversations and a feeling of mutual respect and friendship, the bad experiences I have had with casual dating have left a poor taste in my mouth. 

Last November, I was physically assaulted by a man who I had been seeing casually. At the time of the assault, we had been seeing each other every other day and we had confided in each other about a range of personal issues. I considered him to be warm and kind, and trusted him more than the others. We had developed feelings over time, and I had been preparing to divulge my feelings. 

Even though I didn’t meet him on a dating app, we both spoke about being on them and shared our grievances about dating app algorithms. As it stands today, he is most likely still on Tinder, swiping right on girls who are completely unaware.

Later, in January, I experienced harassment for the first time. I met a man on Hinge and I went on one date with him. He never said or did anything that I particularly disliked, but something about our interactions felt forced and slightly uncomfortable. When he texted me a few days later, I decided to let him know that I did not think we were a good match and wished him good luck with his work. 

He texted me repeatedly for the next couple of days and had attempted to call me a number of times. I had finally decided to block his number and hoped to god that he didn’t remember which address on his Uber app was mine. 

And, of course, there was the man from Hinge who decided to take the initiative of finding me on Instagram after I hadn’t replied to the messages he sent me every day for three days in a row. I don’t even have my last name on Hinge, and I have no clue how he found me, since we have no mutual followers.

A much needed break

For a couple of weeks now, I have decided to take a break from dating. I feel as though I have finally reached the point of fatigue. I’ve started to feel tired of the high of infatuation I have gotten after a particularly good date, and I’ve been left feeling anxious after the bad experiences I’ve had. 

Despite my initial desire to go on dating apps as a learning experience, I’m almost certain my reasons had changed. It had become a form of validation that was simultaneously intoxicating and overwhelming. It was a way for me to avoid feelings of loneliness after leaving my family for the first time. It was also a good way for me to distract myself from the stress of my impending graduation, in addition to my full course load, part-time work, and extracurricular activities. 

After being in a committed relationship for so long, and after the onslaught of the pandemic, I thought being on these dating apps would be fun. And the experience was fun, until it wasn’t.

Overall, I don’t regret my experience. Although the experiences I’ve had have left me feeling confused and empty at times, they forced me to confront the feelings of loneliness stemming from my previous relationship and face them head on. I’ve become better at identifying red flags in a relationship and I’ve learned to trust my gut.

Going on these dates has helped me meet more people and learn from their life experiences. My experiences have led me to discover that even short-term connections can still have meaning, even if they don’t have a ‘label.’ 

After everything, I’m still not quite sure what I’m looking for in a long-term partner. All I know is that I won’t be waiting for any of them to fall in love with me any time soon.

In the meantime, I know that I’ll be just fine on my own.

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