The Art Of Casual Dating

Perhaps I should blame my parents; sometimes I think I might be their karma. I am the byproduct of two of the 80s biggest heartbreakers accidentally falling in love. I remember overhearing my mother on the phone with her sister as they joked about how at 12-years-old, I was already such a hopeless romantic. Naturally, I was mortified as she laughingly tried to convince me why it’s an apparent good thing to feel. 

It’s no wonder that the whole casual dating scene never felt at home to me, considering the foundation of what I once thought dating should look like sat on a pedestal of exasperated proclamations of love—a teenage boy serenading you with a guitar in hand on the high school football field, a grown man standing on your front lawn with a boombox, or even more realistic, a silver fox who leaves you playing the he-loves-you-he-loves-you-not game for an entire decade until he finally proposes with a diamond Manolo Blahnik shoe in an Upper East Side penthouse apartment. 

So you can imagine to my surprise that being raised on scripted romance didn’t exactly set the stage for success in the realm of modern-age dating.

While my parents were the era of going-steady and love ballads, we are the era of swiping and repressed feelings. In the 80s, romance didn’t mean humility or a loss of independence. It wasn’t a tug-a-war of nonchalance, or a who’s-more-blasé contest. But rather, it was as simple as a new chapter with the hopes that happily ever after will be written in the stars. And while I do believe that that type of romance can still exist today, for anyone who’s ever lived and dated in New York City—I think we can all say in unison that finding that “big love” can feel so few and far between since our feelings are challenged in an island of go-getters who ride shoulder-to-shoulder trains every day and yet, have no idea how to say hello. 

For whatever it may be, I found myself diving head-on into dating when I caved and moved to the Disneyland of hipsters, better known as Williamsburg, Brooklyn. As my roommate once put it, I “plucked the pages of Hinge” as soon as I moved in. The evenings that weren’t spent decorating the walls or naming the furniture were spent over cocktails at speakeasies and candle-lit dinners. You would think as a self-admitted hopeless romantic, I wouldn’t be able to pull off the casual dating scene. But for the first time in my life, I felt like I could actually play the role of The Chill Girl© since “getting myself out there” simply meant getting acclimated into my new neighborhood.

And while there was a frenzy of blondies and brunettes, finance bros, musicians and more—what I was left with was someone who would become my first summer fling and a lesson in timing. 

I couldn’t make this up even if I tried. On the literal first day of summer, this year’s Summer Solstice, I was running errands (see: shopping for a new outfit fast) to prep for my date that night. And as I was browsing through the clothing racks, a name I hadn’t seen in years popped up on my phone. It was from one of the first guys I had ever dated in New York. I coined him to my friends and to the Internet as an almost-lover. He was the first guy I dated in the city who I really felt had the potential to go somewhere and in a two paragraph-long text, he shared how he was pretty sure he saw me on the train that morning and went on to apologize for any hurt he may have caused me in the past.

You would think seeing his messages would leave me dumbfounded but instead, I felt light. It seems we always get the apologies we once sought after, once we’ve stopped looking. His apology brought me back to the person I used to be—someone craving love, wholeheartedly, yet had never felt it before. Like clockwork, his texts were a perfectly-timed reminder that even if things don’t pan out as planned, feelings and vulnerability don’t have to be invalidated just because they weren’t experienced to the fullest or didn’t hold up the way we thought they would.

With that, I headed to my date with a guy I had been seeing for a few weeks at this point. On our first date I blurted out that I already liked him because, hi hello I’m Ella and I’ve been embarrassing everyone around me since 1993. Fair enough, his reaction was a bit taken aback. Yet on that Friday night, the first of many that summer, he said to me:

“You’re amazing, damnit, I like you.”

I smiled ear-to-ear for the rest of the night.

He was an actual New Yorker, sans the accent. Tall with a heartthrob haircut, and filled with comments that always made me laugh. While he admitted that feelings weren’t easy territory for him, I felt a sense of comfort fast. We would binge trash TV together as I watched him laugh at the parade of men on The Bachelorette. His quick wit jokes about one particular contestant, one who channeled emotional abuse and admittedly mirrored traits from my previous relationship, gave me a sense of ease I’m not sure I’ll ever fully be able to thank him for. His ability to see through toxicity and manipulation gave me a sense of hope that maybe, just maybe, conflict never had to look like that in a romantic relationship or in any relationship period.

Dating him was the perfect situation until it wasn’t anymore. He was someone who navigated his feelings slowly and cautiously, while I was initially someone who wasn’t looking for anything at all. But as he made me see that romance didn’t have to be so explosive, that feelings could be felt without being projected—suddenly, I wanted so much more. 

He was always patient and open with me as I anxiously threw the “what are we” talk over and over again. It took me awhile to accept that those conversations were really rooted in a longing for a title he wasn’t prepared to give; and over a wine night with an old friend, I finally saw our situation for what it was. Completely out of context, my friend said to me, “Sometimes ‘I don’t know’ is the ‘no’ we’re not ready to say or admit just yet.” Right then, I finally knew the answer to the anxiously awaited “what are we” conversation that deep-down, I always knew but had been avoiding all along.

The next day, my summer fling reached its end. 

At first, I was instantly brought back to the hurt I felt from the almost-lover phenomenon, embarrassed to be feeling so much for someone who was never mine. But as we spent the entire day filling in the blank spaces that finally explained why we weren’t on the same page and why we may never be, his conclusion ironically left me with a title I never saw coming. Despite how everything went with us, he told me I was one of the best people he had ever met.

Just like that, I realized—whether it’s casual dating or a full-fledged romance, we don’t have to fall in love in order to care about each other. And regardless of playing the role of The Chill Girl© or The Hopeless Romantic©, in this moment of my life, I couldn’t ask for more.