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Overthinking Everything: Age Gap Dating

I went out with someone 20 years older than me. Here’s what happened.

I’ve sometimes joked that I have the personality of a 45-year-old man. Then I dated one.

We met by chance during a night out. The way people used to meet one another before the apps, he tells me later. He’s still doing it this way. And not being a fan of the dating apps myself, I was pleased to meet someone in person for a change.

We sat beside one another at a sports bar on the East side of the city. The place probably wasn’t crowded but the alcohol running through our blood made everything seem livelier than it really was. I learned that his name was Marcus. He’d grown up in New York, worked as a software engineer and liked listening to jazz. (Drunk me got really excited about that last one). When he turned to me and asked, “How old do you think I am?” I squinted my eyes the way you do when you’re trying to read a text message still half asleep. “Thirty-seven,” I said confidently. Wrong.

To his credit, Marcus didn’t look 45. Or at least not how I previously pictured 45-year-old-men to look. He was tall. His arms defined. His face youthful. He wore jeans and a plain black t-shirt. White sneakers. And he was out at a bar on a Tuesday at 2:00 a.m., which is even rare for me. His age took me by surprise. But something about him also intrigued me. So when Marcus texted me and asked if I wanted to grab drinks the following week I said yes.

However, I’d be lying if I said I didn’t have some reservations about going out with him. While I’ve sort of always preferred to date older men, fifteen or twenty years seemed like too much. When Marcus was my age I was in elementary school sculpting Play-Doh. That’s weird to picture, right? He’s gone around the sun and seen twice as many moons as me. How could I ever catch up? Although in today’s world where things change as quickly as TikTok trends, I wondered if it would be me or him who’d fall behind?

dating, Age gap dating

On the day of our first date, I was more curious than nervous. The night was going to go one of two ways: either surprisingly well or downright terrible, I decided. As I walked into the restaurant where we agreed to meet, I did my best to look casual – as one does when trying to appear both interested and indifferent. 

We sat across from one another (over candlelight) and quickly settled into a discussion about work and life. I was surprised by how easy the conversation came. We were no longer in a sports bar but a jazz club. And not one of the basement clubs in the West Village. This was a place where cocktails came with floating clouds of smoke and celebrities like Lady Gaga had been known to visit. Though honestly, I prefer the basement jazz.

Afterward, we wandered over to a nearby bar that offered a much more relaxed backdrop. As we talked, it struck me how our age difference acted more as a facilitator than a barrier. Marcus teased me for things that were “before my time.” And I poked fun at him for being out of touch with the latest trends. We shared common interests. Watched the same shows on Netflix. Respected one another’s sarcastic sense of humor. I started to wonder if maybe our age difference could work in our favor.

When I told my friends about Marcus (and his age), you could hear the air being sucked out of the room as they gasped. One friend, in David Rose fashion, just looked at me and said ew. After the initial shock wore off most of them did express their support. “Okay, this could be good. I like this for you,” they said. And while that statement may be a 2.0 version of a backhanded compliment, I agreed that maybe this could be good for me.

However, my friends voiced their support under a veil of skepticism. And maybe they were right to do so. Society does, after all, encourage us to question those who defy relationship norms – sometimes warranted, sometimes not. They asked why he was still single. They wanted to know where he lived. Maybe it was because of all their questions that I later asked Marcus (again, casually) if he typically dates women younger than him.

 He smiled at my question. He knew it had been coming. With a hint of seriousness, he shook his head no. I expected maybe a brief synopsis of his recent dating history. Instead, our conversation unfolded into a thoughtful discussion about the Me Too movement.

Marcus wanted to make it clear that he was not the creepy 45-year-old hitting on young girls at the bar. That wasn’t his game, he said. And I believed him, having met my fair share of creepy older men. Ironically though, this conversation brought us back to the night of our first date where we had stood beside one another while I waited for my Uber home. It was clear that neither he nor I knew how to approach our goodbye. We made awkward conversation until Marcus joked that he didn’t want to be like Cuomo, who just that week had resigned as Governor of New York over sexual harassment allegations). And so, with my permission, Marcus kissed me goodnight.

From this, I knew Marcus was, or at  least wanted to be, ‘one of the good guys.’ He expressed his support of Me Too, but as our conversation continued, our generational differences became more apparent. At one point he attested that men of my generation are the real problem today. This took me by surprise. And I couldn’t resist wondering how much Marcus could really know about what it’s like to be my age right now.

I reminded him that sexual harassment and assault have been taking place since long before the men of my generation were even born (a fact he seemed to have conveniently forgotten). While the internet has provided a platform for men to express outright sexist, derogatory attitudes towards women – after all, my friends and I have a shared photo album capturing the most absurd messages we’ve received on dating apps (there’s more than 200) – the problem dates back much further than Tinder. Marcus nodded his head in response. Point taken.  

We didn’t go out again after that night. But I wouldn’t say it was because of this conversation. It had been an open and receptive dialogue, probably made inevitable by our age difference. Though I don’t think that’s a bad thing. It’s talking about these issues honestly that we expand our understanding. Despite any discomfort it may create, I’ll take a man asking me for permission to kiss me or hold my hand over the men who have treated my body as though it belongs to them any day.

Why didn’t it work out? The short answer is our age difference. But not for the reasons you may think. Instead, as I talked about my favorite band being the Goo Goo Dolls, how I like to cook to the sound of Frank Sinatra, and admitted my ignorance of modern-day pop culture, the more Marcus beamed at me.

“You’re an old soul,” he proclaimed excitedly. “Do you know how rare it is to meet someone your age like you?” At first, I took this praise as a compliment. I felt seen in a way I hadn’t from dating men my age. But after a while, I started to feel like Marcus saw me less as who I am and more as some kind of unicorn – an “old soul” in a young body.

All of this made me ask myself if age really does matter. And honestly, I’m still not sure I have an answer. I think it just depends on the people and what feels right. At least for me, I realized that I don’t want a relationship where age is a foundational element to our union. I want to be admired for everything I am. Not idolized because I don’t spend my free time learning TikTok dances like others my age. I have more to offer than this. I am more than what I am not by comparison.  

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Kate Warrington
Kate Warrington
Kate Warrington is a New York based writer and contributor to She Explores Life, where she writes about mental health, culture and sexual wellness in her column Overthinking Everything. In her words, Overthinking Everything is not meant to be an advice column of any kind. Instead, as a twenty-something woman acutely aware of how little she knows about life, sex, relationships and even her own body, Kate invites us to explore some of the nuanced, and at times laughable, questions of what it means to navigate coming of age. Her work has appeared in outlets including Thrive Global, Forbes and Impakter Magazine. She is also a regular contributor to Medium and previously contributed to the New York City documentary series Stoop Stories. Find more of Kate’s writing at and follow her on Twitter and Instagram @warrington_kate.
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