Middle-aged men having a penchant for younger woman is nothing new. From Greek mythology and Regency literature to Leonardo DiCaprio, it’s a trope we see time and time again. Understandably, for a lot of women, it warrants nothing but a scowl or a knowing sigh.
Recent pictures of Leonardo DiCaprio, 49, and his girlfriend Vittoria Ceretti, 26, frolicking on the Italian Riviera, therefore, come as no surprise. In fact, well-documented lore suggests the Killers of the Flower Moon actor exclusively dates women under the age of 25, so the fact he’s sticking by his Italian model girlfriend (who turned 26 last month, by the way), is something of an improvement (the bar is set so low we can no longer see it).
Even so, Leo has become a poster boy for men with arrested sexual and emotional desires. That’s not to say there is anything wrong with age-gap relationships in principle, but when it becomes a repeated pattern (with Leo, it’s 10+ women and counting), then it’s naïve to suggest it's a coincidence that he only falls for models in their early 20s.
And on this trip to Italy, another one bites the dust. Leo appears to be joined by his childhood friend and fellow actor Tobey Maguire, 49, and a ‘mystery woman’ thought to be the 21-year-old actor Emily Skinner and suggested to be Tobey’s latest romance – just weeks after he was linked to the 20-year-old model, Lily Chee.
Unlike Leo, who has unwittingly built his appetite for relationships with women half his age into his brand, until 2017, Tobey was married to jewellery designer Jennifer Meyer, who, at 47, is only two years his junior. The former couple also have two teenagers together – Ruby, 17, and Otis, 15 – and have reportedly remained close friends since their separation.
Naturally, fans noticed that there are only three years between Tobey’s daughter and his two potential new flames. When he and Lily were seen ‘looking cosy’ at Michael Rubin’s 4th July party, one fan commented on Jennifer’s social media saying, ‘Why is your ex-husband banging someone 3 years older than your daughter?’. The jewellery designer said she doesn’t ‘usually response to such nonsense’, but Tobey was ‘kindly helping a friend to her car’ and ‘being a good guy’. She continued, ‘Now he has [been] blasted online for dating someone he is not. But thank you for your rude comments. I hope it made you feel better today.’
It looks like Tobey is such a good guy, in fact, that he invited another 20-something-year-old on a yacht trip off the coast of St. Tropez later that month. Whether he and Lily or the 'mystery woman' are dating or ‘just friends’ is beside the point; this pattern of wealthy men around the 50-mark spending their free time with women fresh out of education and not legally allowed to drink alcohol in the US is something that makes a lot of people uncomfortable.
For many, it’s hard to imagine what they have in common. While Tobey is most likely thinking about his kids’ looming college fees, these women probably have friends who are still in higher education themselves and are wondering which clubs they can get into after their next birthday. Friends who, as some have already pointed out, are only three years older than Tobey’s daughter.
While he is not the first nor the last person, particularly a Hollywood star, to get divorced only to be snapped with a much younger woman, the optics are far from ideal.
Although there’s nothing to suggest that these women are not free agents, there is a power imbalance embedded in the very culture that makes these relationships socially acceptable. Especially when the older person is a man.
If Jennifer Aniston, 55, say, was spotted in a hot tub on a Greek island with a 21-year-old male actor, it would likely become a huge talking point. Whether people objected to it or not, it would dominate headlines and she would be judged far more harshly than Tobey. Consider Sienna Miller, who has previously had to come out in defence of her relationship with Oli Green, who is 14 years younger than her. Or Jada Pinkett Smith, who had an ‘entanglement’ with August Alsina who is 21 years younger than her. Their dalliance dominated an entire episode of her chat show, Red Table Talk, and led to August releasing a single called ‘Entanglements’. As for Kris Jenner, 68, and Corey Gamble, 43, their age gap is still something she is asked about in interviews ten years into their relationship.
Meanwhile, Leonardo has never publicly addressed his dating lore (despite the infamous graph of his former partners’ ages that regularly does the rounds on social media). And there’s a high chance Tobey won’t either. They are free – whether divorced dads or long-term bachelors – to date whoever they please without it hurting their careers or reputations in any tangible way. But the fact their twenty-something companions barely register on the break-the-internet scale anymore, is a little depressing.
Nikki Peach is a writer at Grazia UK, covering TV, celebrity interviews, news and features.