Navigating Casual Situation-ships: Between Pleasure and Pain

This personal essay was written by a 24-year-old Singaporean female who discovered that despite the allure of casual label-free situation-ships, emotions may complicate matters.

“Hey, so, after this drink, I’m heading downtown to meet my boy friend (read: boy space friend), do you want to come along?” I asked.

It was a Friday night, and I had spent the evening out drinking with an old friend; someone I had been close to since we were both 12. It was our last night out in a while and we didn’t meet often. That said, I had always considered her one of my closest friends, easy. We’d gone a long way, from jamming out to hopelessly romantic songs by Taylor Swift to being fresh grads with our whole lives ahead of us to figure out.

“Sure, if he doesn’t mind”, she responded, four glasses of wine in.


It was odd, because introducing a close friend to someone you had been casually seeing often complicates things. Somehow, introducing the person you are seeing to some of the constants in your life (i.e. friends, siblings, parents) signifies a step forward in your relationship, emotionally. I had been casually seeing Aiden* for around three and a half months now. He was a foreign exchange student who was only going to be around for the duration of a semester, and we agreed from the start that whatever we had between us was going to be casual. It was the perfect arrangement for me— I wasn’t looking to jump into a new, serious relationship and I found him really attractive too. We did not put a label on our relationship but within the first week into seeing each other, we realized that we had a really intense, soulful connection.

*name changed

We were completely honest in sharing everything about ourselves— our dating experiences, life goals and philosophy, music preferences, etc. On our third date, during a long, thoughtful conversation, we came up with a pact— that we would marry each other when we were 35 if we have yet to settle down with someone else. Despite all of that, we were very aware that whatever we had was going to end when he left for home, and we also came to an agreement that we’d remain really good friends, considering the level of connection we had established within one week of knowing each other.

This casual, label-free situation-ship was confusing for me and as it later appeared, for him too. We were very realistic about what we wanted (and didn’t want) out of it, but emotions definitely got in the way.

This casual, label-free situation-ship was confusing for me and as it later appeared, for him too. We were very realistic about what we wanted (and didn’t want) out of it, but emotions definitely got in the way. A week since our first date, I had met his best friend (who flew across the world to visit him); and eventually, I also met a whole bunch of his closest buddies. He told his brother about me, and all his local (and fellow exchanger) friends knew about my existence. I also introduced him to one of my oldest and best friends. Majority of my friend groups had come to know of his existence, and a few of my friends were rooting for us to stay together. Even my dad started noticing that I was seeing someone, and had, on one occasion, popped the question, “Your boyfriend, eh?”

The confusion regarding our situation got more complicated when we sat down to have the talk on exclusivity. We had an honest conversation about the people we were still talking to and seeing since we started going out with each other; about whether we would be bothered if the other continued to do so; about whether we were hooking up with anyone else.

I hadn’t done so when we had the talk, but he expressed that he was bothered that I went out on a couple dates with other people when we had first started going out. He also confessed that he had done the same, but it was emotionally difficult to handle by this point, considering how far we’d come. We ended up agreeing on exclusivity. At this point, what we had was definitely beyond the point of what most people would call a “fling”. We were exclusive. We went for brunches and fancy dinner dates. I slept over at his place half of the nights in the week, and we’d hang out sometimes without getting physical— we would just listen to music, jam out to some of our favorite tunes or (purely) watch Netflix. We’d even planned a couple of trips and talked about the places we wanted to travel to together when the semester ended. I don’t know how this sounds to you, but it sure didn’t sound all that casual to me.

Less than a week ago, I had to say goodbye to Aiden. He made the decision to return home early so that he would not be stuck in a lockdown here in self-isolation without family and friends. We spent almost every night before he left together, not talking about our impending parting. I treasured every night I had left to hold him; and him, me. I picked him and his buddy up and went to send them off at the airport. I talked about visiting someday, handed him some gifts, and hugged him goodbye. The airport, at this point, was empty. The coronavirus pandemic resulted in thousands of planes being grounded, after all. As I walked back to my car alone, I felt exactly like the airport, empty. I patted myself on the back for not breaking down and crying in front of him when I hugged him goodbye. I knew if I lingered for another minute, I definitely would have. I sat in my car, sobbed for a good five minutes and then, drove myself home.

This was not the first time I found myself in a situation like this. Just a couple months ago, I was in the same situation with someone else. This fling became a relationship though— we were cohabiting for three months, and he had met my dad and my brother. The only difference was that I was the one leaving then, and that we had also made promises to hang on to each other and try a “long-distance relationship”. It had definitely started as a situation-ship and back then, I had a similarly realistic view of what I wanted (and didn’t want) out of it. He wanted me to move across the world for him but I was stuck with a dead-end job waiting for me when I returned home. I had finally let him talk me into trying to hold on to what was left of us when he told me I was the love of his life. Somehow, hearing someone tell you that you’re the love of his life hits a little different. Needless to say, that didn’t end well.

Both of my experiences with situation-ships had one thing in common: intense pleasure and intense pain. Both men, however, remain to date, the only two people I’ve had such intense, deep connections with. I had been absolutely head over heels for the both of them. I was absolutely obsessed, and I poured my whole heart into both situations. When they ended, they hurt so much more than when my other relationships didn’t work out.

Somehow, I had been unable to establish a similar kind of connection or desire with the people I had been in long-term relationships with. Perhaps it was the transient nature of the situation-ship. Perhaps it was because we had felt that we had nothing to lose in being honest with each other. Or perhaps it was the lack of expectations that made the connection incredible.

Somehow, I had been unable to establish a similar kind of connection or desire with the people I had been in long-term relationships with. Perhaps it was the transient nature of the situation-ship. Perhaps it was because we had felt that we had nothing to lose in being honest with each other. Or perhaps it was the lack of expectations that made the connection incredible. Navigating a casual situation-ship so intense and real still presents such a conundrum for me: is it worth it to be addicted to this particular kind of pain, over and over, if you knew that it was preceded by intense waves of pleasure and happiness?


“Let’s go downtown, shall we?” I looked up, now five glasses of wine in. I was really trying to hide the fact that I was tipsy and feeling a weird amalgamation of numb-ness and pain altogether. I had just found out that Aiden was going to leave in a week’s time. I felt sick in the stomach, but somehow that sickness came with waves of comfort that we still had some time left.

“Yeah, sure. We could call a Grab now,” my friend responded. “Let’s go hang with your boy friend”. We hopped into the Grab and headed downtown. It was worth it, I thought. Who would’ve thought that dating in your 20s would be so complicated?

Today, I smiled while recalling the last time I had held Aiden in my arms, letting the waves of pleasure and pain wash over me. I don’t regret any of it; it’s beautiful that somewhere, some time, somehow in this crazy world, I met someone like Aiden. What we can’t have anymore now is painful, but what we had back then was beautiful. Pleasure and pain, it’s all the same after all, ain’t it?

Feature image by Shawn Tan, follow him on Instagram @ninelives.project.

For more articles like this, check out our Modern Love/Loneliness column.

a contributor

One of many contributors, sharing their stories under the cloak of anonymity.

5 thoughts on “Navigating Casual Situation-ships: Between Pleasure and Pain

  1. I think situationships work only because women are more confident about what they want when they know that it’s only short term. They’re more assertive, both in and outside the bedroom. If the OP was this confident in her actual relationships, maybe they would’ve gone better? Regardless, this is an incredible piece of writing, and I loved it.

    Liked by 1 person

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