How One Night Destroyed a Lifelong Friendship

I had never been as much myself with anyone else in my life as I was with him. And I walked away.

Wendy Miller


Photo: Zastavkin via Canva

We met when I was 19. He was 20, seven months older than me to the day. I’d just gotten out of a long-term, long-distance relationship, and although I knew one day I wanted to get married and have kids, I wasn’t sure what I wanted in that moment.

We connected instantly. I’m talking about a spontaneous combustion type connection. I, a girl who never ever hooked up with a guy on a first date, hooked up with him on that date. That was the first time the rules were broken when it came to us. It was my rule, about not sleeping with someone on a first date, but breaking it changed the course of things.

We continued to date for six months or so, with the same physical passion. But we also had much more.

We were always laughing together. We always had something to talk about. We enjoyed the same movies, much of the same music, and though we didn’t read the same books, we often talked about what we read.

But we both knew something wasn’t quite right about our relationship. Ultimately, I wanted marriage and kids and commitment and he wasn’t so sure he did. So we broke up.

Well… we ended the exclusive romantic relationship.

But we stayed friends. And we continued to hook up. That was not something I’d ever done with someone I’d broken up with before.

Friends with occasional benefits

Over the next 20+ years, we would be friends. And when we were both between relationships and in the same area, we would reconnect and hook up. It might just be one night in a span of three or four years (or more), or it might be several months at a stretch that we would be together casually. There was no pressure of any kind.

But regardless of our relationship status with others, we stayed friends. He was the one person around whom I was always comfortable being myself. No matter how silly, or embarrassing, or whatever else, I could just let go with him. He might laugh, but it would be with me, not at me.