“Who are you waiting for tonight?” Jon, a bartender who has witnessed several of my dates over the years, asks. He tucks his shaggy hair behind his ear before handing a customer a cocktail, then situates himself in front of me and leans on the bar like an old friend, which, at this point, given I’m a regular at this brewery, he pretty much is.
Before I can answer him, my phone buzzes. I glance down and read the message quickly. “Just parked,” it says. I place it face down and look up to meet Jon’s curious gaze.
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“Just some guy!” I shrug, taking a sip of my beer and drumming my fingers on the dark wood of the bar. “I don’t know. He seems cool. He’s a musician.”
Jon laughs. “Of course he is,” he says knowingly. He knows I have a soft spot for musicians. And younger men. “How old?” he grins.
I shake my head. “Mind your business.”
A few minutes later, I glance to my right and see the lanky 29-year-old I’ve been chatting with on a dating app through the large, garage-style windows. He’s walking quickly because he knows I’ve been waiting, even though I actually don’t mind sitting at a bar alone.
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I like getting to a date early, ordering a drink, and settling in. Still, I find his hustle endearing. I watch him raise his hand to his mouth then release a cloud of smoke into the air before tugging the brewery door open.
He recognises me from behind right away. My long, wavy hair is usually a dead giveaway. I feel his presence behind me, turn my head slightly, and smile before he slides onto his stool.
I’m not often nervous on first dates because the truth is, I don’t care all that much how they go. Why would I? I’m not invested yet, so I’m not overcome by nerves. But not long after he sits down, I’m almost completely at ease. It feels like I’m talking to an old friend who happens to be cute, kind and, well, tall.
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I’ve been on maybe a dozen first dates since one of the most brutal breakups of my life, and I haven’t been interested in anyone. But there is something refreshingly gentle about the way this man talks to me.
He’s nervous, but not overly so. And despite his nerves, he manages to laugh at my dumb jokes. He asks me about my writing career, my kids and my Stevie Nicks T-shirt.
Side note: He’s nearly a decade younger than me. But our conversation flows easily. It doesn’t feel forced. And by the end of the date, I’m fairly certain I’m going to see him again.
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I didn’t always date younger men. In fact, just after my divorce at age 33, I actively avoided it, imagining that a dose of 40-something maturity was what I needed. I was a grown woman with kids, after all. I didn’t want someone I had to teach. I wanted someone I could learn from. Someone responsible, stable. A grown ass man, if you will.
Dating my own age or older (given I was early to marry and early to divorce) just made practical sense. Or so I thought.
I dated around. A lot. I kept an open mind, and I didn’t discriminate based on the usual criteria – job, height, religion. It was important to me to focus on genuine connection rather than checking boxes that, at the end of the day, don’t matter all that much.
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But even with an open mind, and an open heart, more often than not I ended up deeply disappointed by the men I went out with, or sometimes even ended up dating. I did fall in love with an older man – once. But after that relationship imploded, while I continued to seek out what I thought were appropriately aged men for me, I started to feel a sense of hopelessness.
The men I was going out with might’ve been older, but they weren’t more evolved, and they definitely weren’t wiser. In fact, a lot of them seemed to be regressing, as if age and failed relationships had eaten them alive.
Many felt emasculated and emotionally destroyed by their own divorces or past relationships. And while almost all of them said they went to therapy (and even listed it on their dating app profiles), it didn’t show.
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After dating them – or sometimes, just meeting them once – I suspected that they used therapy to make themselves feel better, rather than to actually change.
Age had just made them more set in their ways and that rigidity left me annoyed, hopeless and bored to death of hardened men who said they wanted love but were deeply self-involved.
Meanwhile, on the dating apps, men in their 50s seemed to have no qualms about advertising that they wanted a young, hot, “drama-free” woman. I started to ask myself why I couldn’t date younger.
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Photo Courtesy Of Sarah Bregel
Was I missing out on connections because I had my age filter set to 35+? Maybe. Maybe not. But dozens (hundreds?) of bad dates later, I decided it was worth looking into – even if only for the experience.
So, I started going on dates with younger men. They weren’t all great. Some lived with their parents or were downright toddleresque. But there were some good surprises, too, like that the younger men I was going out with wanted to try new things. They had a spark. They had confidence that was intact. They were fun and open-minded in a way I didn’t often see in older men.
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Likewise, they were more interesting – and interested – and they weren’t afraid to show it. I felt like my confidence in dating had been restored.
Recently, the Netflix show Age of Attraction, which I happily binged, showcased older women dating younger men. While it’s more common in our culture to see older men dating younger women, the series also highlighted the opposite dynamic. And not so surprisingly, some of the women on the show expressed that they felt seen and cared for in a way they had imagined they might never experience again.
As I watched, I felt understood, and at the same time, like I better understood the dynamic I had been living.
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While we’ve been led to believe it’s only men who prefer dating younger, two can play at that game. Anecdotally, dating younger guys may help older women who are still vibrant and full of life feel seen. But some researchers say that women are more satisfied when they have younger partners. And according to 2025 research published in the Proceedings of the National Academy of Sciences (PNAs), both men and women experienced higher levels of satisfaction on first dates with someone younger. Therefore, it’s likely not lack of interest that keeps women from dating younger. It’s fear of judgement.
The end of my date with the younger musician, who did go on to become my boyfriend, was further proof. After he paid for dinner (without even making me reach for my wallet), I invited him back to my house for one more beer. We sat knee to knee on my couch, and my two dogs curled up on either side of us.
We listened to music and talked about concerts and politics before finally, I told him that 11pm was past my bedtime, and he had to go home. I walked him to the door, then stood on my tippy-toes as he hovered over me. A smile spread across my lips just before we kissed for the first time.
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Age isn’t just a number, no matter what anyone says. With it comes experience and new ways of looking at life. But for a lot of older men, whose lives or romantic relationships didn’t pan out the way they’d planned, their experiences haven’t exactly shaped them for the better. It hasn’t equipped them for partnership, love or even romance. It’s often done precisely the opposite.
And to be real, I have enough of my own battles, demons and stressors to fight. I don’t need a man I have to drag through life or who weighs me down or makes me feel heavier. I’d rather be with someone who lifts me up and makes me feel seen, or no one at all.
In the end, the musician and I went our separate ways, for reasons unrelated to age. Now I’m back to dating again at 41, which mostly just looks like staying open to connections, or scrawling my phone number for a cute, younger bartender while paying my tab, like I did last week. It looks like occasional swiping on men from around 25 to 40; I toggle the age limits sometimes.
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I’m not opposed to dating older men again, but I have my guard up with them. Younger men still feel more confident, open and less fragile.
As a single mum in my 40s, I’m not exactly dating to marry. But I am dating with the intention of solid connections, and younger men have been refreshing where men my age and older were mostly frustrating.
I have zero shame about the fact that I’d rather date men who are younger than me. In fact, I think more women should do the same.
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