Leather Jackets, Cats, and Celibacy

They say every Mitski song tells a story of heartbreak, longing, and self-discovery—so naturally, my dating life in Boston feels like her entire discography on shuffle. But then there was Jesse—a leather-jacket-wearing, Lana-loving, eyeliner-smudging enigma who strolled into my Tinder inbox and, for a moment, made me forget all the reasons I hated dating apps.

Jesse was everything I didn’t know I was looking for: tall, lanky, and gorgeous, with a smirk that makes you think 'this man is trouble, and I love it'. He wore his Bay Area stoner vibes like a second skin—baggy pants, a carefree attitude, and a heart full of stories. He just graduated from Northeastern and studied data science, and now works as a freelancer while also working part-time at a ramen shop in Brookline. Whenever he wasn't working, he was shaking ass at the various clubs in Seaport he frequented, like Scorpion or The Grand, and blowing hundreds of dollars on Vodka Redbulls. 

Our first conversation on Tinder was about Mitski—because what gay situationship doesn’t start with a shared love of sad-girl music? On paper, he was just another white twink in my Boston dating roulette, but in reality, he was something more.

Our first date set the tone: sitting next to the Esplanade, passing a blunt, and unraveling our lives. We talked about our passions, our exes, and the lessons they taught us. Jesse opened up about his high school boyfriend and how much of his self-discovery had been stifled by the relationship. I shared my own messy history—less boyfriend, more hookups—and we found common ground in our mutual disdain for disrespectful men.

That night ended back at my place, and let me tell you, the sex was electrifying. It was the kind of sex that makes you forget your own name, the kind that has you rethinking everything you thought you knew about yourself. For the first time, I realized how much I loved being in control, feeling powerful and desired. It wasn’t just about the physical—it was the way Jesse looked at me, like he trusted me in ways I didn’t trust myself.

I missed the way his lips felt against mine, the taste of him lingering like a secret only we shared. The way his slender waist fit perfectly in my hands as I pulled him closer, craving more. I loved how his hair fell over my face like a soft curtain, how I tenderly brushed it aside to see him more clearly. And most of all, I missed the way his scent lingered on me, a reminder of everything we had in those fleeting moments. I didn't just want him, I needed him so fucking bad. 

On our second date we grabbed Thai food from Nud Pob and some pinot noir, followed by more sex that left me wondering if the universe had finally decided to give me a break. By the third date, I was at his place, cuddling on his queen bed, playing Wii Sports, and falling in love with Coco, his rescue tabby from Oman. Coco's previous owner choked and hit her, and left her out in the heat, before she was rescued. She bounced around a few homes before Jesse adopted her from one of his ex-roommates ex-boyfriend. 

Coco was adorable, talkative, and full of personality—a reflection of Jesse’s nurturing nature. Coco had the most beautiful eyes and I loved chasing her around Jesse's apartment, and she was so hilariously sassy. She had every reason not to trust humans, but Jesse had worked tirelessly to earn her love back. Watching Jesse with Coco—how patient and gentle he was—gave me a glimpse of his heart in a way words never could.

But by our fourth and final date—a coffee and thrifting outing—I knew this wasn’t forever. Sitting outside after browsing racks of vintage jackets looking for a black leather jacket I could wear to Legacy, Jesse brought up something I’d said in passing weeks before: that tops often don’t respect bottoms. 

He was referencing a story I’d told him about from Reddit, where a dog owner asked for advice because his dog had stopped listening to him or respecting him after walking in on him bottoming for a Grindr hookup.

Jesse admitted how deeply that resonated with him, how his past partners’ internalized homophobia had shaped his own self-perception. He opened up about his frustrations with labels, his desire to date a vers because he couldn’t handle the stereotypes anymore, and his exhaustion with men in general.

“It really resonated with me,” he admitted. “I’ve been thinking a lot about how naïve I used to be, and even when I topped, some of my exes still didn’t respect me. It’s made me hate labels. I don’t want to be boxed in anymore.”

As Jesse and I unraveled the tangled dynamics of gay roles and respect, I couldn’t help but think: if a dog can lose respect for their owner after one Grindr hookup, what chance do the rest of us have?

I listened, nodding, while he spilled his heart. “Maybe I should be celibate,” he said, in defeat. “I hate men.”

I laughed, agreeing that men are the worst, but reminded him that healing isn’t about avoiding—it’s about growing. My heart hurt a little because I was hoping I could be the exception to his new dogma. 

He asked me about my own experiences, and for the first time, I didn’t feel like I had to perform. I told him the truth: most of my connections were only hookups, but I did cut people off the second I felt disrespected.  I didn't know how to ask for what I needed, and writing them off and being self-reliant was just a whole lot easier. I wasn’t proud of it, but I was learning.

Jesse, as always, tried to make space for me, even while navigating his own uncertainties. He talked about moving to NYC, about needing a fresh start but still loving Boston. He mentioned his ex more times than I could count but refused to dwell on it, saying, “It ended fine, but what he said at the end? Brutal.”

By the third mention, I asked, “Do you want to talk about it?” He said no, but I could see in his eyes that he was still carrying the weight of that breakup. Do people ever get over their exes? Seeing how hung up on their past all the twinks in Boston were, made me want to guard my heart and make sure I never became like them.

When we were back at his place, lying on his bed playing with Coco, there was no sex—just a quiet intimacy that didn’t need words. I could see he was tired, hungover, worried about finances and his next steps. I touched his shoulder gently before leaving so he could rest, knowing this might be the last time we’d be in the same room.

Old Jay would’ve been heartbroken. I would probably be crying and throwing up while sliding down the wall of my shower and blaring Mitski's latest album: This Land Is Inhospitable And So Are We. Jesse was the third-most emotionally invested I’d ever been in a situationship. But after my emotional purging, I felt a strange sense of peace. We both knew this wasn’t forever—our lives were on different trajectories—but for once, I wasn’t stressing over whether he was “the one” or if he checked all my boxes. I was just living in the moment, enjoying the connection for what it was.

Jesse will always have a special place in my heart. I promised to visit him in NYC whenever I’m there, and who knows? Maybe I’ll end up moving there myself. Life is unpredictable, and for too long, I’ve been too focused on the imperfections to see the possibilities.

With Jesse, I learned to stop chasing perfection and start embracing what’s real. Because sometimes, it’s not about where the story ends—it's an opportunity to learn and move closer to what's right for me.