'What I learned from dating younger men in my 40s'
I was 44 years old when I started to suspect dating was over for me. I’d spent the previous few years on and off the apps, but I was mostly swiping left. I’d get into bed at night with the cat beside me, and I’d think about how long it had been since I’d felt the comforting warmth of a man, and then I’d open Tinder or Bumble and watch the bottom of the barrel approach. Not him, not him, definitely not him. I was such a terrible combination: lonely, with high standards.
My 40s launched at a career high, but in the thorny wilds of love and romance, I was shooting blanks. Men my age were dating hot yoga instructors or looking for other divorced people who could understand the compromises of shared custody, while I’d never been married, never had kids. I hadn’t done it on purpose; it just sort of happened. I found myself a prized pony for men in their 60s, but even that wasn’t a sure bet.
A friend offered to set me up with a hotshot movie agent. He was 68, but a very young 68, she assured me. Then she changed her mind. He mostly dates ditzy thirtysomethings, she said, and the punchline wasn’t lost on me. I was too old for the guy who could be my father.
I was visiting a married friend in west Texas when all this changed. West Texas is quite remote, the Texas of the imagination. I was showing my friend Tinder to prove how bad things had got, but when I opened the app, no men appeared. For years, I’d set strict limits on my gentlemen suitors: 36-50; no more than 15 miles away. But I blew out my settings to play the game in the country. My fingers pinched outward twice – 28-70, 100 miles in any direction – and then I slid the phone back in my pocket, forgetting that, with two small drags of my fingertips, I’d just transformed my dating pool.
When I got back to Dallas, where I live, I pulled up Tinder one morning and was startled to find a slew of 28-year-olds waiting for me. They had ripped abs and gorgeous, full heads
of hair. I swiped left hectically to clear the queue of my tactical mistake, but then my fingers paused on one screen. I’ll call him Noah. Twenty-nine, soulful dark eyes, the kind of dreamy good looks you see on a Hollywood actor. And the confounding part was the blue star beside his name. The super-like button, which indicated he’d already chosen me. Was this a catfish? Some kind of prank?
But you only live once, so I matched with him, figuring I’d bail by noon when he proved only capable of speaking in emojis. Instead, I fell into the most gratifying connection I’d found in years.
I wasn’t the only woman making this discovery. The once-taboo arrangement of older women and much younger men has been expanding rapidly thanks to changing social norms and the radical access granted by online dating, which has brought together two groups who might not otherwise mix. In the months and years that followed, I’d meet plenty of women dipping a toe in these waters. Divorced, never married, in open marriages, but all of them having reached the same conclusion: their dating pool was much larger than they’d been led to believe.
Amy* was 41 when she met a 27-year-old on Bumble. Like me, Amy had a successful career, and she found it worked against her with men her own age. She watched friends’ marriages grow strained when the woman became the breadwinner. But this man was proud of her achievements. ‘Not in a “sugar mama” way,’ she told me, ‘but more like, “That’s amazing.”’
In fact, this was the most common reason the older women I spoke to liked dating younger men. ‘I had to minimise my success with people,’ said Jennifer*, who started dating a guy 10 years younger than her after they met at a music festival. It wasn’t until they pulled out their IDs at the bar that they realised the age difference, but the relationship worked.
‘I think he was attracted to me because of my independence,’ Jennifer said. They recently got engaged.
Caroline*, who lives in the UK, also found happiness despite an age gap. She was 44 when she hooked up with a 25-year-old colleague. Her previous partner had died unexpectedly, so while her new lover was partying hard and living in a shared flat in south London, she was a single mother with two young sons and a mortgage. Since their lives were so different, Caroline told herself this was a ‘no-strings’ fling. ‘I was so aware of the huge chasm between our lives and situations, I felt there was no way there could be a relationship,’ she said. Despite Caroline’s reservations, her colleague asked her to marry him on her 50th birthday; they’re still happy together today at 63 and 44. Her advice for anyone considering dating a younger man? ‘It could work out, or not, for so many reasons, just like relationships at any age. Who knows who will get decrepit and die first? The world could end tomorrow. Don’t have any expectations, just give and receive love. Seize the day.’
Noah was a hell of a conversationalist. Quick-witted, deep, with an old-fashioned attention to punctuation and full sentences in our long text threads. He could talk about books, politics, culture; he spoke all my love languages. I assumed younger men would be boring, but the painful truth was that men my own age often were. They’d fallen prey to middle-age give-up, while Noah was still in that thrilling place of discovery. So was I.
Of course I wondered why he’d chosen me. Was this a fetish? Some kind of mummy thing? Noah didn’t find it so mysterious. Older women were interesting, he said, and often quite beautiful. Women in their 20s could be insecure and hooked on social media. When I told my friends about our unconventional attachment, I noticed that women often shared my initial scepticism, while men mostly responded with high fives. Several guys admitted they would’ve loved seeing an older woman when they were in their 20s, but they’d had no idea
how to do it. I found it telling that the people clinging to stereotypes about older women’s undesirability seemed to be the women themselves.
The first time I met Noah in person, I was taken aback by his youth and beauty. Maturity had brought self-confidence for me, but I suddenly felt like every wrinkle, every inch of cellulite on me was circled in red pen. But if Noah noticed these things, he never mentioned them. ‘You have no idea how sexy you are,’ he told me later that week, as I straddled him on my couch. And maybe he was right.
Yes, the sex. Everyone I interviewed mentioned it. Mary* was a recently divorced mum of 40 when she matched with a 20-year-old marine. Their text messages were intellectually stimulating – and then they met in person. ‘What I say to my friends is that boys in their 20s know how to do things that boys our age did not know back then,’ she said. In her younger years, Mary never felt thin enough, or good enough, but the marine helped flip that script. ‘I’ve never felt more beautiful than I have in my 40s,’ she said.
One fear women have about dating younger men is that they won’t want to settle down, as the phrase goes. They are still in that life stage of late-night partying and bed-hopping, and it’s certainly true that trying to forge a conventional commitment with a younger man is a tough ask. And then there’s that future fear: an attraction that sizzles when you’re 44 and he’s 29 will feel very different when you’re 60 and he’s 45. What if he wants children? If Demi Moore can’t make this work, can you? But just because a relationship won’t turn into the relationship doesn’t mean you shouldn’t pursue it. (And maybe thinking there is such a thing as the relationship is a problem.) Can’t we be open to short relationships as well as longer ones? Call it a fling. Call it a love affair. I like to think of it as an education.
My relationship with Noah didn’t last as long as I’d hoped. Different lifestyles, different expectations. And the emotional maturity that all my interview subjects agreed was the biggest potential drawback became a problem in the end, though it’s been a problem with older men, too. But Noah opened my eyes.
I started dating younger men. Not exclusively, but enthusiastically. I have made out with a 26-year-old medical student in the front seat of his truck, and also with a 28-year-old soccer player on the bench of a quaint shopping district, and I have made out with a 21-year-old mail courier on the banks of a lake right before it rained, a double rainbow shimmering across the water. Sometimes I worry this is a rut, but most of the time I think it’s the most unexpected adventure. None of these became long romances, but some became good friends, including Noah. And any sense that dating was over for me had long vanished.
One evening, I lay on the couch of a 29-year-old who’d grown up in Ghana. He’d never dated older women before, but he found me intriguing. All these young guys orbiting around me! ‘Have you ever thought about dating men your age?’ he asked.
‘My whole life,’ I said, putting my bare feet in his lap.‘When I was younger, I mostly dated older guys.’ He ran a hand over my shins. ‘So what changed?’ ‘I changed,’ I said, and smiled. ‘The world changed.’
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