In theory, we live in a liberated age. People hook up all the time without fanfare. An abundance of apps promise to satisfy every sexual or romantic appetite. You’d expect that the brutal truth of swipes and the innumerable schools of fish in the sea would enable people to be direct with one another. And you’d expect that we’d all be swimming in dating successes as a consequence. But as the podcast Modern Love and countless dating shows illustrate, dating is frustratingly complicated. Contra modern pretensions, no amount of seamless communication will ever smooth over the inconstancy of the human heart and the indeterminacy of desire. And tools originally developed to render communication effortless may perversely hinder it, offering, instead, easy avenues to elude uncomfortable face-to-face moments of reckoning. Nuance, mystery, and uncertainty will always be parts of romantic life. Three case studies from my tragically undazzling love life will help us understand why this is so, and why that might not be such a bad thing in the end.


T—. and I matched on an app that’s not exactly renowned for its denizens’ romanticism. I went to his apartment for our first “date,” ironically-slash-unironically worrying that he was an axe murderer. Happily, he wasn’t. After a few dates involving drinks or dinner, I began to think there might be some potential for a friendship with benefits. We discussed our romantic histories. T—. mentioned a boyfriend who he’d been with for a while. The boyfriend lived in a different city and sounded like more of an ex-boyfriend. I brought up ghosting, the practice of abruptly ceasing to communicate with someone without advance warning or explanation. T—. claimed that he wouldn’t ghost somebody, but he confessed that he couldn’t imagine himself breaking up with somebody in person; I don’t have the courage, he said. I thought the comment merited a yellow flag, if not a red one, but I set it aside.

A few months in, he texted, There’s something I need to tell you. My heart sank: nothing good ever comes of such texts. He told me that things were more serious with the boyfriend he’d mentioned than he’d let on at first: it wasn’t exclusive, but they were still technically together. I said there was no problem, that I was perfectly fine with the arrangement we had, and breathed a sigh of relief. Months passed: we dined, we drank, we went to the Whitney, we attended a gala, we went to movies, he met my mother briefly when she came to town.

Over time, it became mysteriously harder for our schedules to coincide. One night, I was in his neighborhood, we hadn’t seen each other in weeks, and I insisted on visiting his apartment since I was literally down the street. He was hesitant but acquiesced. I didn’t acknowledge it at the time, but I could sense him pulling away. He kept delaying and postponing our plans, at one point begging off due to a hangover—this from a man in his early forties. Finally, I decided that the ball was in his court and said so via text. But after eight months “together,” he left the ball on the grass, dropped his racquet, and left the court. Radio silence: no reply texts.


E—. and I matched on Tinder. His photos were charming. His texting put me off: he was crass and made typos. But I figured there wasn’t any harm in meeting. The conversation wasn’t anything special. The physical chemistry was. We went back to my apartment and passed a pleasant hour together. It seemed we’d both enjoyed ourselves thoroughly; he claimed he wanted to meet up again soon.

With that vague promise began an impressive multi-month chain of messages, a string of texts which anyone less masochistic than I would have severed long before I mustered up the self-respect to. E—. pleaded fatigue, he complained of overwork, he contracted a startling number of maladies, his work trips multiplied unaccountably, he remarked upon the distance between north Brooklyn and my Manhattan apartment, he said he was in mourning because Avicii, a Swedish DJ, had died and wasn’t in the mood. Interspersed in this litany of excuses were breadcrumbs of interest, titillating tidbits to keep me hooked. Eventually, we reprised our initial encounter for a grand total of two meetings in over half a year.


K—. had a brilliant smile, an effusive manner, and an impressive physique. I was attracted to him instantly; I didn’t want to come on too strong. His beauty probably subjected him to all kinds of unwelcome attention. I didn’t want to insult him by crassly objectifying him, although sex admittedly was largely the extent of my interest. Instead, we scheduled a date—he ate dinner, I had a smoothie—and chatted about this and that.

We arranged to watch Moonlight together at my apartment: we would literally “Netflix and chill” while viewing Moonlight, one of the most beautifully romantic, melancholy movies of the last few years. I thought the signals were loud and clear. He came very late to the date, bearing an odoriferous tray of tuna fish (a belated dinner). We watched the movie, intermittently pausing to discuss. After a while, it was getting late, and it became clear we were nowhere near the end of the movie. We stopped and discussed life in the city, the loneliness, the difficulty finding friends, our hopes. It was just the two of us, we were seated next to each other, the conversation was getting intense. The tension was palpable, or so I thought.

The conversation paused and we stared into each other’s eyes. Nothing happened. After a bit, he looked at his watch and said we should watch the rest of Moonlight the next day. He also borrowed a few of my favorite books as a follow-up to our conversation, assuring me repeatedly he’d return them after I made clear they were important to me.

Needless to say, we did not watch the rest of Moonlight—not the next day, not ever. After a series of texts, which he skillfully evaded for a number of months, I finally got my books back: we finally met in person again, and he sheepishly handed them to me, apologizing. It was unclear what exactly he was apologizing for.


To a certain extent, these stories simply illustrate my inability to exercise discernment in the realm of romance. Desire clouds one’s judgment—these men were giving off equivocal signals, signals I ought to have recognized from the start. I was guilty of indirection too: rather than communicating my desires straightforwardly, I left considerable room for ambiguity: in E—.’s case, instead of confronting him directly on his ink cloud of excuses and terminating our interaction altogether, I let him string me along in the hopes of another liaison; in K—.’s case, I hesitated to proposition him to prevent embarrassment, disappointment, and objectification.

But these men were also unclear on what they sought and how they wanted to convey it. If we interpret their behavior charitably, E—. and K—. weren’t interested in me and didn’t have the language to say so gracefully. Enthused by our conversation, K—. borrowed my books with every intention of returning them. In the cold light of day, he didn’t want to see me again and couldn’t come up with a smooth way to extricate himself. T—. wanted to end our quasi-relationship but didn’t want to hurt my feelings or endure the inevitable awkwardness of breaking things off in person, so he took the ignoble path of least resistance, withdrawing bit by bit until I gave up in frustration.

In love and lust, we’re buffeted by fluctuating desires—the thirst for attention, the desire to be pursued, the urge to save face, the impulse to preserve one’s pride, the wish to avoid embarrassment, whether one’s own or someone else’s. These desires vie for supremacy, and different ones prevail in different moments. This psychic maelstrom explains why people behave so unpredictably. Subtlety and ambiguity—as protective screens that allow for multiple interpretations of what the other person is thinking, creating a frisson of excitement and deepening one’s interest in the other person—may be inextricable from the art of romance. If you yourself aren’t sure how you feel and what message you want to send someone, it’s easiest to send an unclear one.

One of three sayings carved above the entrance to the Temple of Apollo was the maxim “Know yourself.” The world of romance is a space of self-revelation. We discover through trial and error what we adore and what we abhor, what things are absolute necessities and what we can cheerfully dispense with. All self-revelations carry an element, however minor, of awe and terror: an unmediated encounter with oneself is a fearful thing. Frequently, we hide our deepest desires from ourselves, cloaking our lives in self-deception: only in the erotic realm (and often not even then) are we compelled to confront our wishes in all their naked truth.

Since we’re partial strangers to ourselves and subject to shifting emotional winds, we can only uncover how we feel about someone new and what kind of relationship we seek by submitting to the adventure of romance itself, allowing an affair to unfold at its own tempo. We don’t know the answers in advance. If dating ceased to be a messy experience of discovery and entanglement and became a premeditated, perfectly calibrated process where social scripts were rehearsed and all the rules were predetermined, we would find it less exciting: its power in part lies in its unpredictability. In the age of Covid-19, when we’re beset by uncertainty, such a lesson is well worth learning.