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.

How To Date Post-Breakup: A Lesson in Starting Over

Hair fluffed with musky perfume that I twirled around my fingers — there I was, presenting what felt like an elevator speech for the second time that week. Ghosts from my past and fresh eyes, lip-bit smiles and mini skirts, intoxication under city lights… I couldn’t believe I found myself dating again.

If you told me a year ago that I would be writing this article, I would have been overwhelmed with uneasiness. Because this time last year, I was in the midst of my first love. A relationship that, although was long distance, was certainly worth the mileage. Because no matter what it took to get there, it always felt like home the moment I did.

But here’s the thing — You don’t know what you don’t know, until you finally do. Though it would be a bit of an undertaking to try to summarize why that relationship met its end, I’ll leave it at this: Sometimes, love is not enough.

Fast forward to present day, when I found myself faced with the inevitable first real c̶r̶a̶s̶h̶ crush since my breakup.

There I was, in a Cobble Hill apartment fidgeting with my hair in a dress I just wanted to be noticed in. He offered to cook me steak, an invitation with a weight he couldn’t have ever known about without context.

Because the context was, how one of the most beloved memories I’ll ever have with my ex is the first time he cooked dinner for us. Rosemary and thyme filled the air in my closet-sized apartment as we laughed and drank, while he prepared a steak recipe he had googled in advance. It was the same night he had planned to tell me he loved me.

A little over a year later, and suddenly steak night meant an evening spent in a Brooklyn apartment with someone entirely new, with an oven fan that apparently overpowered anything I had to say. He insisted that he couldn’t hear me, but even when he had the chance to, I would find him checking his phone instead. Meanwhile, across the table, I played coy as I attempted to force a ring I bought earlier that morning to stay on my finger.

But one thing led to the other, and as the night progressed, my ring finally fell to the floor. He told me not to worry about it as his kisses led to his bedroom, and then to the feelings I’d never anticipated spilling out to be met with anything less than reciprocation.

You see, before my ex, all I knew were feelings left on read with the lights off. Before him, all I knew were almost lovers and the thrill of the chase. But after that relationship ended, suddenly I knew very well what it looked and felt like to be in the arms of someone who wholeheartedly wanted to be there, versus someone who just didn’t.

So as I lied there next to him, I wondered if I could somehow resurrect what evolved from that night. After all, for whatever reason, he was still holding onto me despite his words that seemed to fall short. But as I tried to doze off, I suddenly remembered in vivid color the way my ex was so certain about his feelings for me. Though it’s never fair to compare, I couldn’t help but bridge these two situations together. They were night and day, and here I was trying to sleep off the obvious truth that anything other than yes is no. It was then when I knew I had to go.

Which is exactly what I did — until I was outside waiting for my Lyft, which was two minutes away. Naturally, in that exact moment, I instantly recalled how my ring was still somewhere on his floor.

Do I cancel the ride and turn around? Do I try to face him again? Is it even worth it?

I had never felt so embarrassed. It wasn’t so much feeling pathetic for unrequited feelings, but rather, the stark reality of where I was in that very moment versus where I once was, and where I could have been.

Though I must say, the most marveling takeaway I have gotten thus far from dating post-breakup is the frame of reference I never had until now.

Whereas my ex was ready to sing to the hills that he was in love, this guy mustered a “thank you” into his pillow and nothing more when I shared how I liked him. When I left his room to grab my stuff, instead of running after me, he got up to grab his phone.

No, he didn’t and doesn’t owe me anything at all. But once I realized I was never going to get the vulnerability it turns out I’m ready to give, I knew it was time to close the door on someone who couldn’t even walk me to it.

The Lyft pulled up, and I decided to leave the ring upstairs. After all, we just can’t force what was never meant to fit.


Two days and a few swipes later, I met up with a musician at a jazz bar where we bonded over our favorite jazz artists: Ella Fitzgerald, Ray Charles, and all the greats. He shared with me how beyond a good melody, he loves when a song’s lyrics are so intentional, you find yourself not only hearing the song but feeling it with every last word. He went on to share about a particular song he recently discovered that gave him just that — plus a feeling and connection he didn’t even realize he was looking for.

While I’m not sure whether I felt sparks beyond friendship that night, the next morning he sent me the song he had referred to. And from the moment the song began, I knew at least one thing for certain:

Crush or not, he tapped me back into a rhythm worth listening to.

navigating my first "adult" relationship at 25

Before him, I only knew of kisses that were met once the taste of intoxication hit my lips. Feelings were left on read with the lights off and never brought back to the surface unless invited.

It was a lot of what ifs, could bes, and uncertainties as I strolled through cobblestone streets in little outfits with the promise of candle-lit evenings and nothing else guaranteed. As it goes, there were the guys I wanted to feel more with, while there were the ones that I had mistaken lust to mean possibility. Looking back, I like to think both myself and the people I dated could feel that something was missing, even if that missing piece didn’t initially click at first. Maybe, it’s just a matter of finding yourself in a place that reveals why once you stopped searching for the reason.

For now at least, I think I found my answer as to why it didn’t work out with anyone else a few months ago on my rooftop.

Thanks to a gutsy DM I sent and texts-turned-phone-calls...

He traveled across state lines; I prepped frozen pizza à la Trader Joe’s. He wore a navy plaid shirt and bought flowers; I threw on my favorite skirt and spritzed perfume behind my neck. He knocked, then two bottles of red under a New York City sky later, a first date turned into a first love and as corny as it all sounds—it makes sense now.

We are as candid as we are passionate, covering everything from the way we fell, to the way we argue, to the way we love, and everything in-between.

Instinctively, I told myself to tread lightly. Be gentle with myself while simultaneously shielding him from any remote signs of vulnerability. Be an open book, though choose the words I read aloud wisely.

He had been in love before; I had not. And that’s all it took for me to find myself using his past relationship as a standard for who I was supposed to be in this equation.

She seemed as effortless and artsy as I am tousled hair I can’t stop messing with. She was one of the guys, while I always found myself at the girls’ table. And on and on my mind will go trying to dissect and differentiate myself from a total stranger, just as long as it means that at the end of the day, if this all goes wrong, I can say I told myself so. As if filling in the blanks to a relationship I will never know and understand will help me secure my own.

I need to accept that yes, she was his First Love and no, I will never hold that title. But it took their relationship and my revolving door of uncertainties to find myself here.

Here: a place I’ve never known before and yet is similar to those cobblestone streets filled with candle-lit dinners and nothing else guaranteed. Because no matter what my relationship status may be, nothing and no one is promised to us forever. My boyfriend may wake up one day and change his mind about me. Who’s to say I couldn’t either? But the difference is, it’s us.

It’s crying from laughter over the Filipino food we both grew up with; it’s hand-holding at art galleries. It’s jazz downtown; it’s Black Mirror marathons. It’s how we talk about the future with an “our” before it. It’s my heavy baggage and his fingers running through my hair. It’s how we met at a high school football game, and how we didn’t know back then nor do we know now what’s to come.

It’s the way we’ll do whatever we have in ourselves to try.