What Keeps a Situationship From Turning Into a Relationship

There are so many areas of my life I find it easy to exude confidence, but my romantic history has not always been one of them. Throughout my twenties and even into my early thirties, I felt insecure about my romantic relationships because they didn’t always look the way we’ve been told they’re supposed to look. Case in point, my relationship with Charlie, a guy I met 10 years ago at a restaurant in New York City. It started like most New York relationships, I gave him my number, we went out, we hooked up—and repeat. It was a failure-to-launch relationship that turned into a sex-only situationship lasting several years. I was new to this type of relationship, sometimes it was fun and exhilarating, and other times it was disappointing and frustrating.

I had been living in NYC for less than a year at this point and was just starting to date as an adult. I had no clue what I was looking for—I was just chasing the fantasy of it all. Did I want my life to feel like an episode of Sex & the City? Maybe, because I had the same delusions of grandeur of turning the player or the emotionally unavailable into boyfriend material. Only then would I know that I was really worthy. I wanted to be the exception, not the rule. 

This relationship was a never-ending game of cat and mouse. There were always feelings looming beneath the surface, but we pushed them aside for our physical connection while prioritizing our budding careers. He would occasionally joke about dating seriously, but I took it as just that—a joke. Yes, I know this is starting to sound like the plot for your typical cheesy rom-com. 

This kind of relationship is not at all unique—but it’s also easy to feel guilt or judgment from others around a situation where all we get is sex—even if it’s great sex. We all know someone or have been someone entangled in a hook-up relationship—it’s messy, it’s sexy, and it can be painful. Emphasis on painful, when you factor in how these things typically end. We don’t always get closure with people from our past—and there’s even less chance for closure when it isn’t a traditional long-term relationship. We wait for it to fizzle or someone ghosts. And even though I initiated a clean break from Charlie, there was still a lot that had gone unsaid about how we really felt. 

And just so we’re clear, closure doesn’t always make the end of a relationship easier. I’ll be honest, this conversation haunted me for a few days after he and I spoke. It’s not easy to hear the things you wish someone told you all those years ago. Even if you had an inkling about their true feelings, getting that confirmation and wondering what could’ve been is tricky. I had our charts analyzed by Stephanie Whaley, founder of the astrology dating app Oromoon, who told me that on paper we were the perfect power couple—he’s a Virgo sun and we both have our moons in the 10th house of career and purpose.

But I don’t know that I believe there are any mistakes when it comes to the people we cross paths with. People come into our lives for a reason (even if it’s fleeting) to teach us something—if we’re willing to learn.

Charlie, how would you define our relationship?

Charlie: I don’t want to cheapen it and say that we were just hooking up—because I think you and I both know that we wouldn’t be talking today if that was the case. We were two people who, whenever the window of opportunity came, would spend time together and be with each other. 

Charlie: You liked me…

Charlie: I was attracted to you—I thought you were cute. But I also appreciate someone who goes out of their way to talk, and also, I can take a cue. You were kinda funny, and a little nerdy.

Charlie: Yeah, I like to call. I wasn’t a big fan of texting, especially back then, it just felt really impersonal. If I was a girl, I’d want someone to call, not shoot out a text. I still feel that way. It’s just easier to hide behind a text. 

Charlie: Yeah, I was just trying to keep it casual, but sometimes parties are more fun anyway. For me, it’s a much bigger thing than going on a date. If I'm going to a place where people know me, if anything that should be a flattering thing... I wouldn’t bring someone to a party if I didn’t want to show them off. 

Charlie: I did watch Bill Bellamy’s How to Be Player... maybe I learned some things? But no, I think everyone in New York is a fuckboy or fuckgirl. Everyone comes here to date. You’re busy, you end up dating a lot just by the nature of it, the rate of attrition is so high because there’s just more, better, always. You can drive yourself nuts. My whole thing was, I was an ambitious person, very focused, and I was married to my work. My parents are divorced, and I had real fears—I'm not a commitment-phobe, but I knew the strappings of it, so I didn’t want anything that would affect my career and the company I was building. We want relationships, but we also want to have these careers. I was just so focused on that, not that I was pushing people away, but it was hard to put your finger on a relationship. If you're really honestly asking—sure, did I go out on dates and play the field a bit? Absolutely. I think for a lot of us, everyone’s intentions are generally right, but it takes so much to make it work here. If you’re coming to New York for certain dreams, that's the priority. You get into these connections where you like someone, maybe you wanna do more, but they really do take a backseat. And when things get a little stressful, it's so easy to be like, “I’m out,” right? And that’s one thing as I’ve gotten older I realized it’s a huge fucking problem. You just peace out? You don’t work through it? I had some stuff going on, and sometimes you know, you had an attitude and I was like, fuck I didn’t know if I wanted to deal with that. Didn't mean I liked you any less.