Does This Pairing Play Out Well?

The younger man and the older women: it’s become a trend that’s gradually losing its taboo and being accepted as more and more normal. Over the past few years, there’s been a steady stream of famous, beautiful women over a certain age dating younger men: Olivia Wilde and Harry Styles, Lisa Bonet and Jason Momoa, Kim Kardashian and Pete Davidson, Sam and Aaron Taylor-Johnson, Priyanka Chopra and Nick Jonas. Recent movies and TV shows like Licorice Pizza, Succession, and Good Luck to You, Leo Grande feature that same older woman, younger man dynamic. And it’s becoming more common in society at large. But it’s also true that some of these relationships prove temporary. There are still a lot of obstacles to the older woman-younger man pairing, whether that’s lingering social disapproval or the differing demands on each partner as they live through their respective life eras. Here’s our take on the rise of the older woman younger man relationship, what it offers, and what it tells us about romance in the 21st century.

The Appeal Of A Younger Man

What do women gain from a relationship with a younger man? The trope of the Cougar goes back decades, but often films featuring her don’t deeply explore the woman’s motivations or internal life. Now at last we’re starting to hear women’s perspectives on why they might be interested in the younger man. For example, when Cher revealed that she was dating 36-year-old Alexander Edwards, she explained that she finds it easier to be herself with younger men. And Lucy Holden, a writer for The Evening Standard, echoed this sentiment in an op-ed about her experiences dating younger men, observing her younger boyfriend, “he wanted to know what I thought about everything, rather than just telling me what he thought.” She also points out that younger men aren’t necessarily looking to settle down and have kids; she found it freeing to date men with big dreams and youthful idealism.

Another reason older women might pursue a younger man? To have fun! Kim Kardashian famously said this about her interest in Pete Davidson (while also commenting on his kindness and decency as a person). In Good Luck To You, Leo Grande, Emma Thompson’s character hires a young male sex worker to help her climax for the first time – she’s not looking for a complicated relationship with a man her age, she’s just looking for a pleasurable fling.

What Draws Men To Older Women

The Mrs. Robinson or Stifler’s Mom character has long been cast as a one-dimensional sexual fantasy for young men. These representations hypersexualize the female characters, sometimes in a cartoonish way, and they can make light of the genuinely concerning power dynamics that sometimes emerge around age-gap relationships. In reality, young men in serious relationships with older women don’t find their partners attractive because of some culturally ingrained Stacy’s Mom fantasy – it’s often more because these women have gotten to an age where they know exactly who they are.

Male celebrities have voiced the same ideas – Colin Farrell, for example, has spoken openly in interviews about the desire and affection he had for both Elizabeth Taylor and Dame Eileen Atkins, 41 years and 42 years older than him respectively. It’s clear that his desire wasn’t some taboo interest – it was because of who they were as people, regardless of their age.

This is a world away from what pop culture has long ingrained in us about older women who date younger men. Classic films about older women-younger man relationships like The Graduate and The Last Picture Show represent women as tragic figures who we should pity or as broken and selfish cautionary tales. The cultural impact of characters like Mrs. Robinson did underline for audiences that women over a certain age could still be very sexy. But in both The Graduate and The Last Picture Show, the younger man leaves the older woman for a more appealing younger woman, reinforcing the cultural idea that older women are disposable, and doomed to be miserable once a man gets tired of them.

The Cougar stereotype saw a heyday starting in the 2000s, again (on the positive end) drawing attention to women’s sexuality not having an expiration date, and starting to mainstream relationships between older women and younger men. But the Cougar was also fetishized or treated as a joke –not viewed as a serious 3-dimensional person. Countless TV shows feature a plotline where the hot young man dates an older woman and has fun, but it’s always pretty temporary, and it’s typically assumed this is because the woman is cast aside. That’s not necessarily true, though – as Frasier learns when he tries to apologize to the former piano teacher he thinks he “abandoned” and realizes that he was just one in her long line of younger guy boyfriends. When it does work out, the gift of this age gap is that sometimes the pair can shake out of tired cultural expectations and bring new energy to each other’s lives. In movies like The Proposal, and I Could Never Be Your Woman, the younger man’s openness and lack of judgment helps the woman see her own life differently, while he appreciates that she knows who she is and has achieved things. In Don John, the older woman’s greater experience, especially with intimacy, helps John learn to outgrow unhealthy attitudes toward dating and porn that are seriously limiting him in his life and romances. So maybe it’s time we do away with the Stifler’s Mom stereotype to recognize that these relationships often are more transformative and deeper than just a physical thing.

When Age Does And Doesn’t Matter

Paul Thomas Anderson’s 2021 film Licorice Pizza is about the relationship between 15-year-old Gary and 25-year-old Alana, and when he asked about the age gap, he dismissed it: “There’s nothing but the right intentions. That’s not the story that we made, in any kind of way. There isn’t a provocative bone in this film’s body.” But ignoring age gaps is easier said than done in our culture, especially if it’s the woman who is older. Even women are more likely to judge other older women than older men in age gap relationships – according to a 2022 Ipsos poll, 56% of women are accepting of female-led age gap relationships, vs 70% when it’s male-led. This can make being in an age gap relationship difficult, especially for people in the public eye.

There are other obstacles, too – sometimes being in different stages of life makes it hard to maintain a relationship long-term. In The Rebound, Aram and Sandy have a good time together, but as a mother of two, Sandy can’t get over the fact that 25-year-old Aram doesn’t have enough life experience to be a good long-term investment. Similarly, in Bull Durham, Susan Sarandon’s Annie romances the young pitcher Nuke, played by Tim Robbins, but Nuke’s immaturity always feels like an impediment to them staying together — and eventually, she does get together with Kevin Costner’s more age-appropriate Crash. Ironically, that movie is where Susan Sarandon and Tim Robbins got together – and unlike their characters, despite their 12-year age difference, they did stay together for over 20 years. And The Rebound actually has a hopeful ending, too – the pair meet up five years later, and there’s a suggestion that Aram could potentially have matured into a new era so they might have a shot. Sometimes being in different stages of life also means being in different places in your careers, which can make long-term relationships hard. Kim Kardashian and Pete Davidson split after his career started to take him around the world shooting projects, while Kim was in a more established place in her career and, as a mother of four, had to be more home-bound

In Prime, Uma Thurman’s character Rafi can’t get over the fact that her young romantic interest David would have to abandon his burgeoning art career to settle down with her. It’s her who can’t get over the generation gap because she wants him to have a different kind of life — maybe the life that was denied to her.

But not every age gap relationship is hindered by these differences in personal and professional stages of life – Priyanka Chopra, for example, has spoken about how Nick Jonas supported and encouraged her successful and established career. Aaron and Sam Taylor-Johnson made headlines when the then 18 and 42-year-old confirmed they were an item after meeting on the set of Sam’s 2009 film Nowhere Boy. And Sam and Aaron have been going strong for over a decade, raising four daughters (two of their own and two from Sam’s previous marriage,) and even renewing their vows in 2022 to celebrate their 10 years of marriage. Rumors have swirled for years about the pair: some allege that he was really only 17 when they first met and so Sam took advantage of Aaron when they started dating; others even claim that she has been holding him hostage in the relationship for over a decade. But the couple have always maintained that they didn’t get together until after the shooting was over and that Aaron was in fact the one that pursued the relationship because he was drawn to Sam.

Even when age-gap obstacles can’t be overcome and these relationships end up being temporary, that doesn’t necessarily mean they’re not meaningful. In Cha Cha Real Smooth, Cooper Raiff’s Andrew struggles to adjust to life after college and pursues a relationship with Dakota Johnson’s Domino, the mother of Cooper’s brother’s classmate Lola. Cooper’s time with Domino forces him to grow up, handle some responsibility, and experience the kind of life he could have. Domino marries a stable, secure man her own age, but clearly, the relationship was formative for both of them. We’re often conditioned to see relationships that end as relationships that have failed, and maybe relationships that never should have happened in the first place. But sometimes, a relationship just runs its course, and it could be life-changing even if it’s not the final one. Harold and Maude – one of the most iconic and extreme examples of this age-gap relationship – is about a romance between a young man and a 79-year-old woman, so obviously there can’t be a very long future in this relationship. But their love for each other – and their mutual understanding of each other’s morbid sides – makes this union deeply impactful for both in the time they have.

Conclusion

Middle-aged and older women today are getting bolder in voicing their desires – both in stories and in real life. As they express what they’re looking for in a younger man, they’re showing agency and opening up more choices for all women. And sure, maybe those generation gaps are too big to overcome sometimes. But that doesn’t mean you don’t gain something from trying.