Love & Sex

True Stories: What I Learned From Dating an Older Man

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How dating an older guy made me feel too young for my own good.

I felt like the odd one out on New Year’s Eve. I was spending it with my boyfriend and his friends (all of whom were a decade or so older), and our differences were palpable. Recently graduated, I felt directionless, but they had mortgages, established careers, and steady relationships. My boyfriend had ticked off two of those items and was ready for the big commitment, which couldn’t have been further from my mind. I wanted something frivolous and fun, words better suited to a singles cruise. I had a wildly idealistic view of what being a couple entailed, a hazy picture with faded yellow edges: a couple reclining, reading, limbs tangled in a pile of supine contentment. I wanted to live in the carefree ‘70s — ironic given I was the only person in the group who hadn’t been alive during that decade.

My relationship with my boyfriend was slowly failing. We argued constantly. I found him too sensible, too corporate. He wore shoes with Velcro straps, he was punctual, and his taste in music was too mainstream for my liking. Our relationship limped along. We should have broken up over New Year’s Eve, but we waited, perhaps fittingly, until a wedding reception one glorious June day.

In the meantime, my boyfriend had introduced me to R. They were best friends, which made R. an obvious no-go, but I was attracted to him. I knew a lot about him already — he was a reporter, he was divorced, he was acutely intelligent but downplayed it, and he had a dark sense of humor. Shaking hands and exchanging pleasantries, I wondered what he had heard about me. My age, perhaps; the rest I preferred not to guess. 

I wanted to live in the '70s — ironic given that I was the only person in the group that hadn't been alive then.

R. was handsome in a scruffy, unkempt way. He had crinkly brown eyes, a crooked smile, and thick, dark hair. He wore too much black; always a black sweater paired with navy or black jeans. He smoked constantly, hunching his slim frame forward as he inhaled, as though apologizing for a filthy habit.

I had met R.'s girlfriend first, on that New Year’s Eve. Some couples make sense. They weren’t one of those couples. She looked like a swimmer, tall and broad with ginger hair and pale blue eyes. She wore no make-up and she was sensible — I was sure of that as soon as we met. She cooked roast duck and I enjoyed it enough to ask for the recipe. It’s still scrawled in a notebook, never cooked. I watched her boyfriend that weekend furtively, guiltily, and felt I wasn’t deserving of her duck recipe or her kindness.



Amidst the ruins of my relationship, R. and I became friends. After a couple of years, he split up with his girlfriend. We were discussing bands when he invited me over to download music. And he would cook, he added. I arrived to discover it was still their apartment. They were taking turns living there until they sold it. It was tastefully decorated, complete with the clutter long-term couples acquire.

He cooked whimsically and we drank, listening to music. We listened to Nick Drake, then switched to jazz and kept drinking. We were being wistful and pretentious, trying to impress one another. I was telling him about my job offer in New York and he was seducing me with tales of when he lived there. I chose not to check the time. As it grew late he suggested I stay and he would sleep on the sofa, but we quickly forgot that arrangement. We settled into opposite sides of the bed like an elderly couple, said goodnight and turned out the light. Moments later, beneath a blanket of darkness, we gravitated towards the center.

Being with R. was easy. He was laid back and funny, kind and generous. He was honest with details about his life; his marriage and subsequent divorce, the places he had traveled and the times he lived abroad. I listened attentively in wide-eyed wonderment, finding him much more fascinating than men my age, more fascinating, in fact, than me. We were both dreamers. We were writing novels in our spare time, or rather we were talking about writing novels in our spare time. Mostly, we were drinking Pimm's, or hosting barbeques, or lying in Hyde Park.

But, like everyone, he had flaws. His melancholy dominated conversations with searing intensity. I stopped finding his self-deprecation adorable, instead finding him defeatist in ways I didn’t like or understand. He smoked excessively, but talked about quitting in a detached, noncommittal fashion. And he drew out my insecurities, dropping references I didn’t understand. “You’re a teenager,” he’d say jokingly, and I felt like one. I was twenty-five, he was thirty-five. I was still drifting and trying to play catch up, which was proving difficult. I couldn’t even trump him with my decision to move to New York — he had already lived there.

His life was full of complications. My life felt dull and predictable compared with R.’s; clean, compartmentalized, and distinctly lacking in gritty residue. Suddenly I longed for the messy details his life was overflowing with. And as I realized I wanted to emulate him, to become more impetuous and boldly embrace the disasters and upsets, the snags and impediments, I became aware of something else too. The influence in our relationship was one-way: the flip side of dating someone with such great stories, whose life is positively bursting with experience, is they’re not as receptive, as impressionable. They’ve already checked that period off their list — or at least, he had.

R. got in a bike accident, a collision with a car that sent him flying and broke several ribs. A little later, we drove to Cornwall together. It was May, but the sand still had the coolness of spring. We paddled in waves, drank wine, and savored our solitude. I turned and smiled into his shirt. We ate ice cream and with sticky fingers returned to our hotel room.

We kissed, before simultaneously noticing a small bird perched outside, watching quizzically. Laughing, we moved to the bed. I was on top of him, moving carefully, when he winced and reached for painkillers. I rolled off the bed and ran a bath for both of us. Leaving him to grow wrinkled, I threw on a light dress and got ready.

As we were leaving for dinner he glanced at my feet. “White sandals?”

I looked down. “Yes?”

“They’re very… white,” he laughed. “I I’ve never seen shoes that bright before.”

I frowned. They were a cheap, impulse purchase. I studied them closely, and they looked cheap and impulsive. Suddenly, with absolute certainty, I despised them, and they didn’t like me either, pinching at my feet like small pecking birds.

I wanted to act content, but I was hurt. Like his "teenager" comments, he'd turned me against myself. I hated my shoes and him for mocking them. Our conversations were usually fun and meandering, but now, I started arguments for the sake of it.  

“Are you annoyed with me?” he asked as we walked home.


But by then the wine had sedated me, mellowed me out a bit. The shoes were still technically on my feet, but had already mentally been discarded, never to be worn again.

“Well, that ruins my theory,” he said. “No one ever argues about what’s actually on their mind.”

“I like that theory,” I said, too proud to admit it applied to us an hour earlier.


One night we met my ex, his best friend, the one who had introduced us. He had taken the news of our relationship well initially, but that evening was a different story. The meal ticked by slowly. Without provocation, he made a snide remark about R.’s salary, or, more accurately, the lack thereof. It was rude, but I let it go. He clearly wanted to feel some semblance of an upper hand, but really, he needed only to wait a few more weeks. R. and I split up as my job in New York became a reality.

“I just don’t see the point in a relationship with an expiration date,” he said flatly.

“We could try long-distance,” I offered optimistically, but as I uttered the words I knew it would never work. I liked him, admired him, but I didn't want to be with him forever.

I congratulated him, but I was struggling with this neat conclusion of loose ends. It felt like a bad Woody Allen movie.

We met up in New York a year later. There was no awkwardness or tension, just the fondness that comes from a relatively mutual breakup. It was a balmy September evening, so we sat outside and drank beer. He told me he was engaged to the ex who looked like a swimmer and that my ex was the best man. I congratulated him, but I was struggling with this neat conclusion of loose ends. It felt like a bad Woody Allen movie. I was thinking about the big day, the inevitable jokes in the best man’s speech. A speech I wouldn’t hear. For a fleeting moment I felt like the odd one out again, just as I had on New Year’s Eve. But things weren't the same, I realized with relief.

Sitting across from R., our roles had changed. Now I was the one regaling him with tales, talking about the best summer of my life. In the year since our breakup I had moved to New York, knowing only two people, and thrown myself into new experiences, saying yes to every invitation until I was exhausted, but finally driven, no longer directionless. Dating R. had highlighted what I was seeking in my own life, a life that had felt decidedly sanitized and predictable compared with his. But it no longer felt that way. I couldn’t see the future on that September night, how much worse it would get before it would gradually improve, and keep on improving. I could only look backwards and realize how far my life had unfolded since my break up with R., how much I had grown by understanding life doesn’t develop neatly and according to plan. My life didn't look exactly like a hazy yellow picture from the carefree '70s, but it was starting to develop some frayed edges, and the character and direction I'd always wanted it to have.