I always thought that casually dating — and doing it successfully — was a myth. An urban legend that only a few lucky people could experience.
This is partly due to the fact that a relationship’s success is generally determined through its longevity, the most successful being “until death do us part.” The very nature of a causal relationship goes against this premise. While I’m sure there are a few unicorns out there, who have dated the same person casually for decades, that’s not typically how a casual relationship plays out. Most commonly, the relationship escalates into a committed, monogamous relationship, or it fizzles out, with both parties simply over the fling, or because one person starts to care for the other person more.
But somehow, this past year I successfully dated someone casually. Even though neither of us got too attached, we were still able to have a meaningful relationship. This was after many failed attempts at casual dating.
It started on Grindr, a popular gay dating app. (Who am I kidding — it’s a popular hookup app.) My profile mentioned that I had just gotten out of a serious relationship and was looking for something with no strings attached. But after the second time of meeting up for casual sex, I realized I could see myself liking this guy. He’s one of the sharpest, most interesting, well-read people I’ve ever met. More important, he found my obnoxious sense of humor funny, even endearing.
So I took the risk, and invited him on a proper date — to see “The Slutcracker,” a sex-positive spoof of “The Nutcracker.” We grabbed some drinks before the show. It was different talking to him fully clothed; somehow, it was more awkward than our naked pillow talks. During the show, our jitters slowly dissipated and we held hands.
After the date, we purposefully didn’t have sex. I wanted him to know that I liked hanging out with him, regardless of whether or not we were being physical. I wanted him to know that even though our relationship was founded on sex, it could become more than that.
Thus officially began our casual affair, which lasted six months. Once a week we would see each other for dinner, a movie, show or drinks, and then after we would head back to my place to snuggle up together. During the week, we’d text each other. Not every day. Only when something popped up that made us think of one another. Usually something in the news or a book recommendation. He encouraged me to read James Baldwin, which opened my eyes to a literary world I didn’t know existed.
But our relationship didn’t naturally fall into this comfortable groove. We had a few big talks accompanied by a few big reveals.
He was the first to bring it up, on our fifth date or so. “So what’s going on with us?” he asked. I’ve heard this question from partners before, and it’s one that always makes me cringe.
I told him the truth — that I liked him but couldn’t date him monogamously. My last relationship took quite a toll on me psychologically, and I wasn’t in a place to commit to someone again. While he was visibly hurt, clearly hoping for another response, he respected my candor.
He told me he liked me, too, and while he was hoping for something more, he said he wanted to continue hanging out.
I was skeptical. I’m known by my friends to be a heart-breaker and thought this was a recipe for disaster. Then, I figured, he’s a grown man who can make his own decisions. If he got hurt in the end, I’d have no reason to feel guilty, as I was honest from the start. Besides, I liked him. I wanted to see where this relationship would go.
I did, however, want to keep him honest in the relationship, so we ended up having multiple talks, what I would call check-ins. I know this sounds like a corny tool a marriage counselor would suggest to a struggling couple, but these conversations didn’t feel forced. The premise was simple: Are we okay with how things are going in our relationship? Are we finding ourselves really falling for the other person, and would we like to take things to the next level? Or, given that both of us were busy with our careers — me as a writer, him as law student — was this level of commitment ideal?
These check-ins kept us on the same page, and we promised we would be honest about our feelings and expectations.
This past fall, he left for Paris, so before he left, I booked us a place in Provincetown, Mass., for a final hurrah. We ate delicious food, held hands and kissed in the street, and took in some of the freedoms that can come only from being a majority in a space. Drunkenly, on a stoop on Commercial Avenue, we did a final reflection on our relationship.
We agreed that we were happy with how it went. This casual dating thing was new for both of us, and yes, we both had some regrets, but overall it worked.
He regretted having a wall up, he said, something he did to protect himself. When I initially told him I needed something less serious, he withdrew emotionally, fearing I’d hurt him. He rid himself of the possibility of dating seriously because he thought I would always be opposed.
Despite our honest talks along the way, I didn’t suspect this was happening. I felt guilty — even foolish — because after he confessed, it seemed so obvious. I figured he was too busy with law school to see me more than once a week. But in actuality, he was keeping his emotional distance.
The thing is, I would have dated him more seriously, even called him my boyfriend. I needed more space in the beginning, but I didn’t articulate strongly enough when I was ready for something more.
Sure, I was enjoying the pleasures that come from not being committed, namely sex with others, and yes, there were a few folks in my life that I was dating casually at the same time. But I would have been willing to give all that up. If only I had known.
After this talk, I realized there’s nothing casual about casual dating. It requires the same level of honesty and communication as dating someone seriously. While we tried to be open about our feelings, expectations and needs from the relationship, we were still far from perfect.
However, our causal relationship still worked because we at least attempted to be honest with each other as much as possible. We didn’t lie about the other people we were seeing, although we didn’t flaunt our other relationships or sexual encounters. We didn’t play any “hard-to-get” games with one another, both admitting early on that we did care for one another. We simply feared rejection. We feared that in saying we wanted more, we would lose what we had. That was where both of us could have done better.