WHAT KEEPS A SITUATIONSHIP FROM BECOMING 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.
Read the edited interview below, or become a paid subscriber to listen to our full conversation.
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.
With my friends, I would refer to you as a fuck buddy or to my therapist, I’d say you were the only guy I had casual sex with for an extended period of time, but I guess that does kind of cheapen it after hearing your definition.
Charlie: You liked me…
Yeah, we’ll get into that. To set the scene for everyone, we met 10 years ago at Fat Radish in New York City. We were seated at tables next to each other. I remember I overheard you and your friends talking about Justin Bieber, someone said something mean about Justin—and I love Justin—so I interjected, and I was like, “don’t talk shit about Justin!” That kind of opened the floodgates for conversation. What was your first impression of 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.
Wow—no one’s ever called me nerdy. We talked for the rest of the brunch and then when you left, you asked for me and my friend’s number—which was hilarious. But I knew you were going to call me. And you actually called me, like on the telephone, which scared me a little. I didn’t answer, but you left me a voicemail, and this is going to age us, but you invited me to a party at Sway.
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.
Was it intentional that you asked me to go to a party and not on an actual date?
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.
Back then, did you consider yourself a player? Or a fuckboy as they’re called these days.
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.
You’re talking about me and my attitude?
Charlie: I knew it was good-hearted, you were never mean. I can only talk for myself. Yeah, maybe I played at times, but with us, it was so easy to have one bad moment and be like, “ugh fuck it. I’m gonna do something else.” I’m mad at you, whatever, time goes by, and then you’re like, oh, I really liked that person.
Speaking of bad moments—let’s get into the infamous incident we had. So, I think after we had hooked up a few times, we were texting one Sunday, I was at Tiki Disco drinking all day, you were doing whatever you do. You texted me to see what I was doing and if I wanted to come over. I took the subway from Brooklyn to SoHo—by the time I got out of the subway, I didn’t have a text response from you after I said I’m heading over, but I knew where you lived, so I just went to your apartment. I buzzed the door, I was let into the apartment building, and when I got to your floor, your apartment door was open. So I walk into your big SoHo loft, and it’s dark in the room except for the light of the TV. I see you sitting on the couch with another girl. I honestly still remember this like it was yesterday. You turned to me and just said, “oh, you just felt like stopping by?” And I’m pretty sure I gave you a death stare. I didn’t even say anything. I just turned around and walked out.
Charlie: Yeah, it was pretty awkward. But I was not with that girl. One of my roommates would always go out, get drunk, bring girls home, and then just pass out. So, she came back out of his room and we were just chatting. When you came in, I was like—oh shit, this is not a good look. I was mortified. It totally fucked up my night with you. There was no way for me to talk my way out of that. I was too young and dumb to be like, “I can explain!” It was a comedy of errors.
I was definitely viewing you through the lens, this guy’s a player. I was really bummed about it because up until that point, I liked you. I don’t know that I thought you were going to become my boyfriend, but I had feelings for you because I was a 25-year-old girl and I was sleeping with you, what else happens. So the next day, my friend was like, listen, if you still wanna keep seeing him, just say that you were drunk and smooth it over. So that’s what I did. I texted you and apologized! Even though I absolutely did not need to! You said it was cool, we were fine, but we didn’t talk again for a couple months.
Then eventually, you started texting me again. It was very much the situation where you were texting me late at night, on the weekends, sometimes I text back and then don’t hear from you. So I got this sense that I was on the back burner or that I was your backup choice when you couldn’t find anything better.
Charlie: I don’t think anyone was on the burner. I remember we always had our little text banter back and forth. Sometimes it worked, and sometimes I’d be like, alright, that’s not gonna happen. I’m sure it still goes on, but it felt very generational. Busy working people trying to have the normalcy of a relationship, but not taking the real mature steps to do that and setting the time aside and having those conversations. I have regrets about some of the ways I’ve acted for sure. I don’t really judge myself too harshly, I don't think it was a meditated thing, but I knew better. I just also wish that we did more. That’s the travesty of the whole thing.