The Year of Casual Dating

a toast to the trenches of contemporary courtship. and another to delusions of heartbreak

My friends and I, like many young adults on the internet, often refer to the dating scene in our city as "life in the trenches". Rather crassly alluding to the utter misery, filth, and hopelessness of trench warfare - we joke with each other about the fact that we’ll probably have to move to a different city if we want to find a soulmate. Just two days ago I heard myself say aloud, “I think I’m getting bitter”.

“I think I’m getting bitter” was a phrase spoken by none other than Carrie Bradshaw, over 20 years ago, on Sex and the City. Carrie, callous towards her many romantic failures, is a woman in her mid-30s who had fun in her twenties. She partied, dated around, built a career, and established a sense of selfhood that she now wears proudly. But now she is in her 30s, and she is bitter. Bitter towards society’s sickening love affair with the “biological clock” - one that starts ticking when you turn 29 and ticks faster and faster with each passing year. Bitter, also, towards a desperate pursuit of love. One she is close to giving up on after years “on the market”.

I am 26. I have been on the dating scene again for about a year and, already, “I think I’m getting bitter”. A few days ago, I was unceremoniously dumped for the third time in four months. Most regular people after the first dumping would take time off to recover from the recent blow. I, condemned with an almost compulsive desire to be talking to someone in a romantic or flirtatious capacity at all times, get back out there within a week. The dumpings were all a bit different. “I’m not over my ex.” “I’ve been talking to another girl.” “I need to focus on myself".” But each time, to varying intensity, a thought rattled around in my brain: “they’re just not that into you”. Another phrase spoken on Sex and the City - this time by Miranda.

Between romances, or whatever they are, I toil with this idea almost incessantly. It bothers me. Each dumping destabilized something about myself. This thing being that I can no longer distinguish between romance and scarcity.

I spent the first half of my single year enjoying the casualness with which I could flit in and out of partnerships. An experiment I’ve coined to close friends and dates as “Seinfeld Dating”. Like in Seinfeld, you see one person for a month. Treat them with the respect you would treat a partner (not like in Seinfeld). Go on actual dates - the movies, a restaurant, an art gallery. And ultimately learn something from each other before moving on to the next person. This was obviously an imperfect plan. Feelings get hurt, and eventually you yearn for something stronger. But this was a period which afforded me a feeling of control.

When I began to angle my approach in pursuit of a romantic relationship, control became much harder.

It would be easy for me to pathologize the way I navigate romance. That I am “anxiously attached”. That I move things too quickly, or obsess over inconsequential exchanges. Was it their unavailability that allowed me to fill in the blanks for myself? Make up instances of passion in taciturn gaps? Or were real instances of passion then quickly forgotten the moment they no longer saw a future in me. With each dumping, I cried to them. I asked why. I told them that their desire to stop dating me was for no reason other than that they were, indeed, “just not that into me”. They looked at me, or breathed softly into the phone, unreadable.

In the moments I am not depriving myself of compassion, I tell myself that there is something deeply corrupted about contemporary courtship. I get drinks with my friends and we complain about the trenches. We say we “need to leave this city”. If we stay here we will end up spinsters. We step into this bitter mist of casual self-inflicted misogyny to soothe our wounds.

We make allowances for the men we date where they would not for us. We talk up their personalities to our friends, refuse to show their pictures. We build visions of them in our minds and smudge out less desirable traits. Dealbreakers do not exist in this world of romantic scarcity. We sleep with these men and stay awake in their beds. Lie nose to nose and trade secrets. But the suggestion of dinner feels like an overstep. Grabbing coffee in the morning or meeting more than once a week are a ticking bomb. We have more access to physical intimacy and nakedness than the most standard courting rituals. To ask for those is to move too quickly. We are not “owed” these practices. When we are dumped, we are told that we are not “owed” more than we are given. Because, in casual dating, no one is owed to one another. No one is each other’s.

The loss of a situationship is not your own. What is your own are the things they made you feel, or perhaps the feelings you made up about them in your head. Because in times of romantic scarcity, it’s hard to tell the difference between what is real and what desperation invented. The thing about casual dating is that it is deeply corrupted. It is the trenches.

I could settle into this story of corruption. I could tell myself that men are terrible and that romance is decaying. But when I peek out of the bitter mist, the men who dumped me are in relationships. I step out of the mist myself in my brief moments of infatuation and I see people in love. I see people connecting. But in the mist, we cheers to the trenches. We look at the men around us, the men we used to date, our friends, and the ever-decreasing ages of their partners. We say, like ourselves at 19, 20, 21, 22 - “younger women don’t ask for rituals”. They laugh at tired jokes, which are new to them. They do not think they’re getting bitter. They also have no control. Definitely less than we do. It’s wrong, but we hate them.

In the trenches, younger women pose personal threats to our mortality. As I dye my greys for the first time in my life, obsess over my “biological clock” (I could pathologize this as a symptom of my OCD), start to relate to Sex and the City, and start to become a postfeminist cliche, younger women are dating the men in my life. So I date older men to feel less mortal. In the depraved recesses of my mind, I would like to feel precocious again. To be seen as vibrant and lively and “smart for my age”. This is how it is in the trenches.

Not all rejections are heartbreaks, but all rejections are heartbreaking. By this I mean that of the three people who dumped me, I only had real romantic feelings for one. But that in all three instances, I felt the true heartbreak of being rejected, cast off. And with each new rejection, I become more embittered. I toast with my friends and we grovel in our mutual pains. We soothe each other with “fuck him’s” and “it’s girl’s night tonight’s” and “he’s a narcissist’s”. We do all these things to avoid the lurid emptiness of “he’s just not that into you”. I never really believed these men were “just not that into me” when I said it to them, as they ended things with me. I said it because I was hoping faintly in the back of my mind that they would say otherwise. That they would say it was all a mistake and that they took it back. But even as they said “no, that’s not it” I could see it in their eyes. And the look was blank. It’s that blankness that we try so hopelessly to forget, as we cheers to the trenches. 

We stumble through the miasma of the dating trenches and tell these stories of corruption to keep moving forward. The utter emptiness of rejection and failure are too hopeless. It’s easier to sit in the trenches than to feel like three dumpings in four months is more than a coincidence. That, rather than being a symptom of romance perversed, it might just be me.

I entered a year of casual dating to build my independence. And a year out, I am more independent. I’ve had wonderful, thrilling experiences and pushed myself to do things I had been too terrified to do. But I am also bitter. And the reason I wrote this is because, as hopeless and heartbroken as I feel, I don’t want to be bitter. I want to summon enough strength to recognize that, while the world of dating has evolved alongside the decay of human connection, there is no great conspiracy against me or my friends. I don’t have some ghoulish personality that I am unaware of. Dating is hard. Heartbreak is hard. But we do them to feel more human. And to do the most human thing of all is to boldly accept each and every time that horrible, empty idea: he’s just not that into you. But someone else will be.

Image: The Mosquito Net, John Singer Sargent (1912)