Confessions of a Dating App Amateur

In 2017, I packed up my life and moved from Pennsylvania to California for college. It was a lot of newness — a new, scenic setting, an updated routine, and after a few weeks of settling in, I met a new romantic interest. That interest escalated into a permanent tenet of my life. Six years later, our relationship took us from Santa Barbara to New York City, where we shared a 400-square-foot apartment and a new life. We made it to about seven years until that connection waned and the cocoon we built suddenly felt cramped. While we were dating, I’d listen to my friends’ dating app mishaps — relieved that I didn’t have to navigate what sounded like treacherous seas, and the menacing stereotypes that exist within the NYC dating pool. The model who covers his biceps in Carhartt and dabbles in coffee because it inflates him with more purpose than just being a pretty face. The content creator whose to-do list is full of “film GRWMs,” “stare at myself in the mirror,” and nothing else. The list goes on. But when my relationship ended, I was faced with the harsh reality that while we had been together, the dating landscape had completely changed. 

I was suddenly a dating app amateur. A dating app virgin, if you will. My friends teasingly labeled me an “adult baby” when it came to dating. Others assured me that this was optimistic, a new start marked by hope and rediscovery of the self. I was now 26, single, and living in New York City. I mean, things could be much worse. Was this my chance to live out my “Sex and the City”-fueled fantasies? At the beginning of what we’ll label my single era — a rather momentous occasion, as this was my first time occupying that category in all of my 20s — I felt ready to put myself out there again. I remember reaching out to a friend and asking her to refer me to Raya. 

I had zero experience with Raya; its interface was as foreign to me as TikTok may be to your elderly grandmother. I submitted my application (which was really just a more formal way for the app developers to ask, “Who do you know here?”) and hoped for the best. A few days later, an email appeared in my inbox alerting me that I had been accepted to the platform. I skimmed the email, locked my phone, and carried on with my day. Over the course of the next few weeks, the app popped into my mind — I toyed with which images of myself I’d lead with…maybe the one in the metallic sheer dress? Or maybe I should have my hair down in the photos? I mulled these small details over in my mind, but I never revisited the app, never completed my profile. It still sits dormant to this day. 

I’m not really in the business of half-assing anything. You can fact-check that with anyone I know. When I go for something, I really go for it. So what in the world was holding me back from making a few swipes on my iPhone screen and joining this community of connection? The easy answer is fear. But I’d like to think it’s more nuanced than that. 

As you can imagine, the breakup was an unprecedented shift in my life. This was my first serious partnership, and therefore my first gut-wrenching detachment process yet. I felt that I was not only detaching myself from a connection that had reached its course, but also the part of myself that needed to rely on others to feel whole. I was naive to think that that process would be hasty. I know patience is a virtue, but it's not exactly a virtue that I’ve fully mastered. Setting up dating app profiles just weeks after we went our separate ways felt like I would’ve been shifting that same dependency from one person to a bunch of potential suitors instead. It still didn’t feel productive for my self-betterment goals. I thought it would be easy to jump back into the ocean — because there are plenty of fish in the sea, right? — but these were uncharted waters for a beginner swimmer like me. It was becoming increasingly apparent to me that I couldn’t just swipe my dependency away. 

Another aspect of the virtual dating arena that never quite sat right with me was that scrolling through people (real! people!) like they’re DoorDash meals kind of game-ifies the whole process in a way that makes me feel a little uncomfortable and icky. I know most of the world has caught up with this new technological frontier (and I don’t say this from my saddle atop my high horse), but I wasn’t sure if I wanted to participate in that game just yet. I was still waiting for my grief to pass, and I didn’t think I’d be able to perform to the best of my ability.

So I wrote it off. I never signed up for any other dating apps. I’m involved in a very social industry, so I also figured I could give IRL connection a shot. But it didn’t take long for me to realize that some of the same dating issues arise, whether you meet your candidates virtually or not. For some reason, I thought that meeting someone in an “organic” way would sugarcoat the outcome. That that ever elusive “invisible string” — which is so thin it’s almost imperceptible — would suddenly spur the romantic ending I’d been looking for. But it turns out that the fickleness of potential suitors' hearts doesn’t vary by the source of the suitors. The game remains the same, either way. The rules unchanged. So the same question seemed to pose itself over and over again — should I play the game, or not? 

I knew I wasn’t alone. It’s definitely uncommon to be a dating app amateur in our current landscape, but I thought looking to others’ experiences could help me look deeper within. Other dating app novices weighed in. Some have maintained long-term relationships, eradicating the need for virtual connection, while other singles shared my same hesitancy. 

“I intentionally avoided dating apps because I felt there was no real substance or soul on them. I think you can only get that real connection face-to-face,” a fashion professional, Noor Turk shared. A few anonymous sources echoed her avoidance of the apps due to their lack of intimacy. “My most intimate, intense relationships have always been meeting IRL. You catch a glimpse of someone at a party, walk up to them, and say hi…the rest is history. You don’t get that sort of chemistry, mystery, or rush when you’re swiping,” one expressed. 

Another source added, “I’d love for everyone to stop living behind their phones and actually take a risk!” While a couple more followed suit: 

“Energy never lies, and you need to be able to feel and see that. There’s something so magical about connecting with someone in person and that initial spark that I think is impossible to capture through an app.”

“There’s something unsettling to me about the ability to so precisely curate and control a first impression, knowing it will realistically only be interpreted at a glance. Much like any social media, it feels reminiscent of a college or job application: you have mere seconds to make a lasting impression. By its very nature, it initially strikes me as impersonal.”

It felt instantly relieving to discover that my uncertainty had company. As a people person and the certified worst texter ever, I also prefer to interact with potential romantic interests in person; it allows me to properly read their body language and mannerisms. But I also received some insights that were beginning to erode my trepidation. 

First, some shared thoughts on approaching modern dating in more creative ways — “One thing I started doing recently is asking people around me if they know anyone they could set me up with. It creates a much more comfortable scenario for me: there’s already a bit of built-in trust, and the other person gets a sense of who I am. That feels so much nicer than trying to judge someone based on a prompt or a joke they wrote online,” PR assistant Olivia Dworakowska shared. 

Editor Jordan Goldberg weighed in with a perspective I hadn’t considered: “My perspective on dating apps is two-sided. I think meeting organically, or IRL, is great, of course. That's what I did, and it worked out wonderfully! That being said, I think that you have to meet people where they are... and single people are on dating apps.”

“The advice I give friends when it comes to dating right now is that I think you have to have your feet on both sides of the line. Go out and meet single people where they are: think bars where games are on, concerts, the West Side Highway?! And make sure that when you're in those environments, you're comfortable to make the first move, the same way you would send the first message on a dating app! And then, keep tabs on your dating apps. I just think it's important not to label yourself a ‘dating app person’ or a ‘not a dating app person.’ Do a little of both and see what sticks.” 

Had I been limiting my horizons by strictly labeling myself as the latter? Was I playing the game with a self-inflicted injury? I resonated a lot with Jordan’s sentiments, because, again, I’m not really in the business of half-assing things. So why was this tentpole of my life any different? Maybe I’m just confessedly a coward, or maybe, just maybe — I’m expecting a watched pot to boil. Maybe I was just spending too much brain power on the topic entirely?

There’s a viral screenshot from an old Instagram story Jemima Jo Kirke shared a few years back, in which she’d been answering questions for some of her followers. A user posited, “Any advice to unconfident young women?,” to which Kirke responded, “I think you guys may be thinking about yourselves too much.” Blunt? Yes. But it was the truth. I realized that this quote applies to many situations, and I revisit it often in moments of mental turmoil. When it comes to dating apps, maybe I have let my pride get the best of me. Maybe I’m just thinking about it too much altogether. Maybe it’ll feel right when it feels right. And in the meantime, I’ve got a very full life to keep me occupied. 

Dating, I’ve learned in my year and a half since my breakup, is indeed a game — whether we want to label it as such or not. When you play most games, your participation is also a relinquishment of your pride. You have to surrender yourself to the possibility of rejection in the same way that you submit yourself to a potential loss when you opt into any game. But the issue is that losing Scrabble feels like a lot less of a personal blow than being rejected for your personality, disposition, physical appearance, et cetera. I’m well aware that there are many reasons why a relationship may not reach its full potential, and many of them are much more nuanced than the aforementioned list — but I don’t think I’ve built up a tough enough shell yet to be an aloof player. And that’s okay. I think I’d want to approach the “game” when I’m feeling one-hundred percent ready. And that may not be tomorrow, or even the next day. But one thing is for sure — the apps aren’t going anywhere.  And while dating may be a glorified game, it’s certainly not a race. Slow and steady wins the race.