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.

when love isn't enough

Last weekend, Facebook reminded me that the first time he cooked dinner for us was a year ago. I wore a velvet dress, he had on a satin tie. I poured the wine, he cooked the steak. Between the stove light casting a spotlight on him, and the sound of candles flickering in the background, I found myself exposed when he asked me why I was looking at him the way I was.

For as long as I can remember, I’ve struggled with eye contact. It always seems to give way to the parts of myself I figure are best kept in the dark. It’s why I became a writer—I like to think I have a sense of control over the trials and tribulations in my life. I’m an open book, only under the condition that each word is carefully rehearsed until perfected. I’m a hopeless romantic who ironically never thought would find love until it looked me right in the eyes. The smell of thyme and rosemary filled the space in my apartment when I realized I was in the arms of someone who wholeheartedly wanted to be there.

He was the feeling of home in unknown territory. He was warm, familiar, and a stranger all at once. It’s the recipe he used that night, the one that I still have folded in my closet-sized bedroom.

There is no perfect love out there. I’ve seen the imperfections that were in my parents’ relationship. I’ve consumed them in movies, novels, and songs that I can recite in my sleep. They are found in the heart-to-heart confessions shared over wine with my closest friends. Every time, the same conclusion always seems to find its way—just because love isn’t perfect does not mean it wasn’t there or that the love was right or wrong.

Our relationship ended because our arguments evolved into toxicity that neither of us deserved. Maybe words slipped out of our mouths before we could grasp them. Maybe there is such a thing as being too comfortable with one another.

What I do know and what I will always hold to be true is that toxic moments don’t make toxic people. We are human and sometimes we just don’t know where to go. All we can do is try our best, even if our best looks a little different than we thought it would.

What I never could have anticipated is the question I have come to now: a year has passed and suddenly, I am not so sure that I am ready for anything, at all.

I remember back when he and I first met. We were 15-years-old. I had on purple eyeliner and braces while he sported floppy skater boy hair and a goofy smile. We dipped out of my high school varsity football game and found ourselves at a grocery store across the street. We laughed without caution as we ran recklessly through each aisle with tunnel vision. Everything was so light.

Before him, I could not imagine having The One. I couldn’t imagine waking up next to the same person, families colliding, and a future with an “our” before it. Before him, all I knew were my quirks, my darkest secrets, my hopes, and my wildest dreams. I knew all of these things and could not for the life of me imagine meeting someone who would want to enter this world that I have kept so tightly shut.

Since the breakup, I am pretty sure I have watched and read every “How To Get Over A Breakup” video and thinkpiece the Internet has to offer, five times over, until my sleepless mind could finally be put to rest with the lights turned off. Eventually, I realized that the advice I was so desperately seeking was there all along, staring right back at me, once I was ready to see it for myself.

Sometimes, love is not enough.

He was my First Love. In one line, he had me crying over laughter. In one weekend, he had me hiding tears behind my sunglasses as he drove away. He understood me in a way I never thought to understand myself.

It was bottles of red sipped under a New York City skyline. It was hand-holding under Christmas lights. It was my emotional baggage and his fingers running through my hair. It was slow dancing in the middle of the street as he hummed in my ears. It was the blurred lines in our relationship that couldn’t be ignored. For the good, the bad, the ugly, and the everything in-between, our love was clumsy, candid, and unabashedly us.

Perhaps it’s OK that we are no longer those kids running around a grocery store without a care in the world. Maybe love doesn’t have to be right in order to be felt. I can only hope that one day, we can share a steak like we used to and laugh until we cry, as we learn to befriend the parts of ourselves we don’t know how to resolve just yet.

No, it’s not going to be the same, but maybe that’s the point.

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.