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.

i'll take my time

Today, I’m going to wake up, brush my teeth, and comb my hair, but I won't feel like I'm in my skin. 

I’m going to walk into work with a smile on my face and a touch of lipstick—the finishing touch to the grand finale where I pretend everything is as sweet as the Splenda in her coffee. No, I may not be able to move mountains today, but I'll be composed as I stand quietly to myself in a crowded elevator.

Today marks 11 years since my mother passed away, and I still hear her voice saying to me, "Take your time, I'm right here."