The conversation that changed everything

^{By Ronan Hale}

I'll just dive in. I’ve been dating my girlfriend for almost two years now and I love her more than anything, but we recently had a conversation that I just can’t shake. I wish I could. I’ve tried to file it away as “just one of those talks couples have” but it keeps circling back like a song stuck in my head, except the chorus makes me sick to my stomach.

How we met

For context, I met my girlfriend in late 2022 when a friend of a friend introduced us at a birthday dinner in Brooklyn. I almost didn’t go that night. It was cold, I was wiped from work, and I was in one of those moods where I felt boring. But bailing felt worse than showing up, so I went. And boom — roughly fifteen minutes after my arrival, she walked in wearing a cream sweater and these big gold hoops, and I swear the energy of the table shifted.

We ended up seated across from each other. She ordered a whiskey neat, which surprised me in a good way. She laughed at one of my dry comments, not just politely, but with this real laugh that crinkled the corners of her eyes.

And by the end of the night, I was fumbling for a way to get her number without seeming obvious, until she handed it over before I even had to ask.

Building something real

The early months felt easy in a way nothing else had. Weekend brunches turned into lazy afternoons in bed. We’d go to comedy shows, double dates, take the train out to Rockaway in the summer. My friends liked her immediately. She was quick with jokes, but also the first to ask how someone’s week had really been. My parents liked her too, which is saying something.

By the time we hit the one-year mark, we were serious-serious. Talking about trips we wanted to take together. Saving Zillow links for houses we couldn’t afford but dreamed about owning one day. I started picturing her in my future in a way that wasn’t just romantic but practical. I wanted her there for the long run.

Of course, there were fights — about money, about how much time I spent at work, about the fact that she hates when I let laundry pile up. But nothing we couldn’t bounce back from.

If you’d asked me in early 2024 what the relationship was like, I would’ve said: solid. Really solid. The best I’ve had.

The night that took a turn for the worst

It didn’t come out of nowhere. We were lying in bed on a random Tuesday after watching a movie about kids in college. It got us talking about our own dumb college stories. She told me about sneaking into bars with a fake ID, how her roommates used to dare her to kiss strangers at parties. I told her about a disastrous spring break trip where I lost my wallet in Miami.

It felt lighthearted until she went quiet. She stared at the ceiling, fiddled with the drawstring of my hoodie, and then said, almost under her breath:

“You know, I’ve been with… a lot of people. More than you probably think.”

I laughed. The comment caught me off guard.

"What's a lot? More than ten?" I said.

She laughed.

"Twenty?" I followed up with, not even thinking twice if I was ready for an honest answer.

She laughed harder.

And right there, that exact moment, I wish the conversation ended. That in itself was hard enough to swallow. But it got so much worse.

Twist the knife

She told me the number. And then she added color I wasn’t ready for. That in college she’d had a “reckless phase” where she hooked up constantly, sometimes with people she barely knew. That for a while she thought it was empowering to “collect experiences,” even if they were messy. That she did things then that she “would never do now” — threesomes, hookups in bathrooms at clubs, drugs (yes, plural), casual one-night stands with guys whose last names she never learned.

She said it calmly, not proud, not ashamed — just honest. Like she’d carried it long enough that she didn’t want it to sit between us unspoken.

I nodded, forced a half-smile, told her it didn’t change how I felt. And in the moment, maybe I believed that. Or maybe I just wanted to believe it.

But inside, I actually can't put into words what I felt. I won't even try.

The reel I can’t turn off

Since we had that conversation about two weeks ago, it’s all I think about. Not just the number, but the specifics she gave me... the images I can’t scrub out of my head. Her in a club bathroom. Her with two people at once. Her climbing into some stranger’s bed just to prove she could.

I hate that these are the details that stuck. It physically makes me ill. I hate that I’m now comparing myself to people I don't even know and wondering if I’ll ever measure up to whatever wildness she used to chase.

It even has me thinking, does she miss it?

And I'd like to think I'm not the overly jealous type. Like, a little jealously is healthy, and I think I'm pretty standard there. But this is insane. It's not even jealously, it's honestly... disgust. It's like she handed me a film reel I didn’t ask for, and now it plays on loop in my head over... and over... and over.

Masculinity, ego, and all the rest

I’ve tried to unpack why this bothers me so much. Part of it is ego. Men are fed this idea that our partner’s purity — for lack of a better word — is tied to our worth. It’s toxic, I know, but it’s everywhere. Movies, jokes, locker room talk. We grow up being told not to care about feelings, but definitely care about being “the only one.”

So when I hear I’m not, some stupid, primal part of me feels diminished. Like I’m less special. Like the bond we have is less rare. Even though I know logically that’s not how relationships work.

The other part is fear. Fear that she’s comparing me to what she’s already done. Fear that I’ll never measure up. Fear that one day she’ll wake up and think, “I’ve had better.”

So for those of you still reading and probably saying "so just break up" — I hear you, but it's not that simple. I still love her obviously. And I don’t want to be with anyone else. I don’t want to lose her. I really don't. Ninety percent of our relationship is still everything I want. She’s smart, funny, supportive, beautiful. I trust her with my life.

And yet… I don’t trust myself not to spiral when I remember that conversation.

It feels unfair to both of us. Like she’s being punished for being honest. If she’d never told me, I’d still be blissfully ignorant, wrapped up in our bubble. Now I’m in this weird limbo where nothing has actually changed — except everything has.

So what now?

I haven’t told her how much it rattled me. I don’t want her to feel ashamed of her past. I don’t want to make her regret opening up. But the silence is heavy. She can probably feel me pulling away in subtle ways.

I wish I could just get over it. Or better yet, that the conversation didn't happen in the first place.

But it did, and here I am, with no idea how to move forward.