Apparently, as a single, straight, 40-something woman, what I really need in my life is a man in his 20s. Or so suggests an interview with Sienna Miller in Vogue’s Winter 2024 issue. She’s been dating Oli Green, a fellow actor 14 years her junior, since the pandemic, and as proof of just how well not minding the dating age gap is working out for her, she appears on the magazine’s cover against a rugged seascape, lensed by Annie Leibovitz and pairing chunky knitwear with a resplendent baby bump.
History and pop culture are of course studded with examples of women who’ve taken younger lovers, from Catherine the Great and Elizabeth I to Madonna, Sam Taylor-Wood and Priyanka Chopra. Even so, they’re exceptions to an enduring double-standard encoded by biology and propped up by centuries of misogyny. The #MeToo movement may have turbo-charged feminism’s progress in the bedroom but, while men dating down in age is simply a fact of life, there’s a lingering vibe of mockery and salacious scandal when the gender roles are flipped. The older woman has tended to be either fetishised and objectified as a cougar or a MILF, or else her desires are minimised and made safe with references to toyboys (yes, that word is apparently still in use). Even when women tell their own stories – the press seem to print one every few months or so – they can’t help making a burlesque of their erotic yearnings, enthusing about their partner’s stamina while harping on their inability to decode the youthful jargon of his sexts.
Miller, refreshingly, avoids all of this, which is why I found myself more intrigued than I’d expected to be by the interview she’s given to accompany those Long Island beach shots. Admittedly, the “wisdom” we’re told she sees in Green, exceeding that of older guys she’s been involved with, smacks of aged dudes insisting on the “maturity” of their decades-younger squeezes, but she’s surely on to something when she notes this new generation’s sensitivity to intimacy’s gender dynamics. After all, 20-somethings have come of age in a radically changed era. Men in their 40s were raised on Baywatch, saw women’s equal rights watered down to “girl power” and ladette culture, and watched unquestioningly the public humiliation of Monica Lewinsky. By the time Green and his contemporaries began dating in earnest, even Page Three’s days were limited.
The idea of such broad-minded, baggage-free reconstructed masculinity is almost as beautiful as the sculpted forms in which it comes packaged, a seductive romance hard to resist for any woman who’s experienced ghosting, breadcrumbing and “situationships” without having the language to name them, never mind navigated the expansive grey areas that until all too recently fringed consent.
How much of this is fantasy, though? That Gen Z men have done the work and are supposedly in touch with their feelings is an oft-touted boon, but having spent a portion of my 30s shuttling back and forth across the Atlantic, I have dated enough intensely therapised New Yorkers to know this to be overrated. Ultimately, their ability to articulate precisely why they’re unable to commit doesn’t change much.
And it’s not as if Gen Z doesn’t have its own issues, either. Just listen to campaigner Laura Bates, who told me when I interviewed her for this paper that the algorithmically perpetuated bile the likes of Andrew Tate direct at young men today is “lads’ mags on steroids”. And then there are the unrealistic “sexpectations” of a generation whose earliest exposure to erotic intimacy is likely to have been violent porn.
As a friend of mine advises, it’s more realistic to think of younger men as works in progress – in other words, just like the rest of us only with increased malleability and a willingness to learn. She’s now edging into her mid-40s and began dating younger guys when they started pursuing her in her late 30s. She’s never been self-conscious about it, and finds them more upfront about their feelings – less neurotic, too. She’s invariably the one to call time on the relationships but not usually for age-specific reasons. And yes, I gather the sex, since I know you’re wondering, is more than satisfactory.
So am I persuaded? If anything, I’ve tended to date older – significantly so on occasion. I’d like to think I’m open-minded (to be anything else is so ageing, right?) but when I went on a couple of dates with an attractive, smart and very tenacious 22-year-old back in my mid-30s, his default enthusiasm kept making me want to describe him as puppy-doggish, nixing any latent chemistry. Moreover, there’s no denying that if you peer far enough ahead, age gap relationships in any configuration are sure to end gloomily for at least one partner – sooner rather than later if you’re a woman knocking back perimenopause vitamins as your perfect younger lover realises he’d like to have a family.
Miller and Green have sailed over that particular hurdle, and her pregnancy perhaps helps make them so easy on the eye as a couple. Not only are they equally good-looking, they appear pretty much of an age. Perhaps what’s most interesting about the Vogue shoot is that, even while theoretically his more slender years and her glitzier status flout hardwired, albeit outdated, relationship norms, in other respects, they’re visually reinforcing them. Both images of them together show him with an arm slung casually but protectively round her – easy to do as he’s significantly taller than her.
Apropos of which, one last thought. While a Match.com poll in 2020 found that 81% of women are open to dating someone 10 years younger than they are (happily, nearly 90% of men were interested in dating someone 10 years older), the figures for women willing to date a man shorter than them are infinitesimally smaller. Which actually makes this particular 40-something woman feel a teensy bit smug: I may be too much a product of the retrograde 1990s and simply not woke enough to ever date a Gen Z-er, but as my dating history shows, I can be as fluid as the next person when it comes to a partner’s height.
• Hephzibah Anderson is a freelance journalist and critic
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