Might I Suggest a Reverse Age-Gap Relationship

New York City is making a cougar out of me

On the eve of my twenty-eighth birthday, I decided to take a walk. It was a bitterly cold twilight in late March and I wandered over to the river where I sat, bundled and breathless, taking in the beauty of the night, the sky so cold it looked like it was about to crack and the ice caps bobbing on the rolling surface of the Hudson. I felt older, I did, and I was thinking about Joan Didion’s essay, “Goodby to All That,” which had been on my dashboard for the past year as a reminder of what was coming for me. “In retrospect it seems to me that those days before I knew the names of all the bridges were happier than the ones that came later, but perhaps you will see that as we go along,” I thought to myself. I was no longer at the beginning– of my time in New York, of my life, and I felt that acutely and accepted it as well, with something like relief.

As I sat there shivering and pondering, out of the corner of my eye I noticed a guy approaching and before I could gather what was going on, he was upon me and gesturing for me to take out my headphones.

“Hey,” he said, “I saw you from over there and thought you were beautiful and just had to come and say hi. What are you listening to?” he asked.

Now, normally I would encourage this kind of boldness and self-assured bravery that seems to be dwindling with the scourge of dating apps that have crippled people’s ability to talk to one another, but, I am always slightly wary of someone so boldly breaking social convention. It’s like being asked out at the gym or the airport– nice in theory in a rom-com sort of way, but in actuality, when that’s happened to me, the guys have, without exception, turned out to be very strange.

I told him I was listening to Gracie Abrams (is there a better soundtrack for despondent reflection?) and we started chatting. As he spoke I took him in. He was cute, or was he not? I couldn’t really decide. He was tall, with nice hair, but was wearing a lot of silver, turquoise, and leather jewelry, like the Jack Sparrow of Manhattan. I was still wavering on whether I was going to give this character my number when he bluntly asked my age. Funny you should ask, I thought, and told him, on the last day I could, that I was twenty-seven.

“Oh cool,” he said, “I’m twenty-two.”

Twenty-two. It was like the stunned silence that happens in the moments after a server shatters a bunch of glassware in a crowded restaurant. Twenty-two! Oh, and his name was Buster. Buster is the name of the cartoon bunny from Arthur, not the guy you want to tell your friends you’re dating. I thanked him for coming over and wished him a good night and then pressed play on “I Love You, I’m Sorry.”

Me sussing out this Buster character

That’s not the first time I’ve been approached by someone younger. In fact, in the last few months I’ve been getting approached by exclusively younger men. In the fall I went out with a twenty-five-year-old who carried himself with the swagger and confidence of a much older man. He pursued me with such certainty I felt compelled to give him at least a shot and then, to my surprise, we ended up seeing each other for a few months. In my early twenties I never would have considered dating younger. I was married to the Mr. Big fantasy, the romantic idea of an older, financially secure, experienced, capital-M Man.

At the same time as I was going out with the twenty-five-year-old, I was also seeing a Mr. Big type. At forty years old, he was thirteen years my senior, which is a lot of years. He was twenty-three when I was ten. He was thirty-five when I was walking across the stage to collect my college diploma. He was navigating middle school clique politics when I was born, and lots of other perverse configurations. Still, I thought my younger man would pale in comparison to the older guy’s appeal. He owned his absolutely massive downtown apartment, had built an impressive career and was a thoughtful and honest communicator thanks to past relationship experience. He was also OLD, like old-man-old, like I-have-to-be-in-bed-by-nine old and no matter how much I liked talking to him over luscious, expensive wine, I couldn’t imagine him coming over and hanging out with my four roommates or traipsing around the Lower East Side for another and then another round of drinks. I’m tired of this grandpa, I wailed to myself, and hopped in an Uber over to my younger man’s waiting biceps.

Me debating between my older and younger guys

My younger man was endearingly eager and surprisingly sincere in his interest in me. He texted me back immediately, made plans consistently, and never left me guessing. I was puzzled. Weren’t young bucks in need of training? Wasn’t I going to be collateral on this guy’s path to becoming a fully formed adult who knew how to treat a woman? I thought I’d do all the work of whittling him into a decent guy just for some other woman to reap the rewards when he inevitably ended things but he seemed to have graduated from boot camp and was treating me with respect and care. I was initially wary of his lack of relationship experience but when my older man started drifting back into his ex-fiancée’s life, I was grateful that he didn’t have any significant past loves to complicate things.

Things were going so well between us that I cut things off with my Mr. Big. I was having fun and starting to see myself with him, picturing a life where I wore his hoodie to breakfast and he came over to watch Summer House with my roommates, but I got ahead of myself. As I tried to crack his veneer and really get to know him I discovered the gulf in our maturity and the mismatch in our life experience. He seemed more interested in my boobs than anything I had to say, and the dates he coordinated were consistently on his turf and at his convenience.

One night, after having the type of sex I had in college (bad, one-sided) I couldn’t fall asleep. I looked at the person curled by my side, the straight line of his clavicle and the face he made while he slept that made him look much younger and thought who are you? Then I turned on my back and stared at the sterile, white ceiling and thought what am I doing here? and the second I thought it I knew I would never spend another night in that bed again. I had caught a glimpse of something I couldn’t unsee, the undeniable truth of how momentous a thing we were doing, how intimate, how irrevocable. I felt suddenly certain that he didn’t recognize the seriousness of what we were entering into. Perhaps it was due to the blissful ignorance of being too young to predict the ways a person you love can hurt you. In a way I was envious of him, of what hadn’t happened yet, the unimpressed placidity you get so ephemerally, before the pain of loss textures your life. I felt sorry for him, for everything he had still to discover, but resigned. Your turn to learn it, I thought, my turn to leave.

Me having an existential crisis while watching him sleep

I am currently seeing another twenty-five-year-old. After my last go-around with my younger man I was admittedly reluctant to take him seriously. Probably unfairly, I keep underestimating his interest in me and his seriousness about our burgeoning relationship. In some ways dating has gotten harder as I’ve gotten older. My starry-eyed romantic buoyancy has waned, and in its stead is a guarded wariness that I’d like to relinquish. My younger man had me over the other night for a picnic on his rooftop. He made a charcuterie board and Aperol Spritzes and he brought up things I’d told him on our previous date that made me realize how carefully he’d been listening.

From his rooftop I could see the tips of buildings scraping the summer sky, the inky black Hudson reflecting the lights of the city in the distance, and I felt it for a moment again, the hopefulness, the optimistic sense that something wonderful could happen at any second. I looked over at him looking at me. At any second, I thought, maybe even happening, right now.