Reeling in the Years: Hollywood Edition
We’ve done the math on the most head-turning couples of the season
As award season rounds the calendar once again, Hollywood A-Listers in their best designer duds are strutting down the red carpet with the sexiest accessory of all: a super-hot, super-inappropriately-aged other half dangling proudly on their arm. In a town/time where the 17-year-gap between George and Amal feels banal, only the weirdest and wackiest May-December romances turn heads anymore. That said, some surprising new pairs are earning our attention (and it’s not always the good kind). So without further ado, in order of noteworthy to jaw-dropping, your nominations for the 2026 celebrity couple age-gap awards are…
Sydney Sweeney & Scooter Braun: 16 years
Though this young(ish) couple’s age gap isn’t particularly large numerically, 28-year-old actress Sweeney gets a courtesy nod from us for repeatedly choosing much older men. As of September, it’s uber-rich 44-year-old record exec Braun, whom she met at even-richer Jeff Bezos’ Venice wedding. The Bieber-founder-turned-Swiftie nemesis, a divorced dad of three, follows Sweeney’s former fiancé Jonathan Davino, now 42, whom the Euphoria starlet started dating at the tender age of 21. Not ready to settle down, obviously, Sweeney’s would-be starter marriage was called off as romance rumours swirled about her Anything But You co-star Glen Powell. Alas, at 37, he was far too young to sway Sweeney’s good jeans.
Leonardo DiCaprio & Vittoria Ceretti: 24 years
The Oscar-winner’s meme-worthy romantic history is the stuff of internet legends; a viral chart proved that the 51-year-old’s girlfriends – among them, Giselle Bundchen, Bar Rafaeli and Blake Lively – never surpass the age of 25. But DiCaprio’s current love, Italian supermodel Ceretti is 27 – therefore, born while Titanic was still in theatres – proving Leo’s “Under-25 Rule” is negotiable and his emotional growth is slow but steady. For those who’ll never let go (and/or are totally convinced Jack could have fit on that door), Ceretti, too, is said to be “different.” Well, she is brunette – and maybe DiCaprio’s feeling his clock ticking. Could he surprise us like Clooney and suddenly settle down? Anything’s possible.
Kris Jenner & Corey Gamble: 25 years
How young is too young to date? According to that old high school math equation: half your age plus seven. Most of these couples definitely do not fall within the “acceptable” guidelines but this one adds up: 70-year-old momager Jenner calls 45-year-old Gamble her “ride or die” – and he’s three whole years older than the unofficial cut-off. They hooked up at designer Riccardo Tisci’s 40th birthday celebration in Ibiza a decade ago, having lots in common (Gamble was a manager, too – Justin Bieber’s tour manager, no less) and some good timing, as Jenner had just separated from then-husband, soon-to-be Kaitlin. Gamble immediately popped up on Keeping Up With the Kardashians in 2015 (his subplot? Loud sex with Jenner keeps Kim up all night) and appeared on his sugar mama’s arm at her 70th birthday, for which Jenner gifted herself something extra special: a brand new $100,000 face that looks fantastic.
Sean Penn & Valeria Nicov: 35 years
Forget anything plus seven – all mathematical equations are off if the person you’re dating is younger than your own child. No doubt 65-year-old Penn’s daughter Dylan, 34, isn’t thrilled to make awkward conversation with her dad’s 30-year-old girlfriend, model/actress Nicov. Penn’s an age-gap hall of famer, having previously dated Charlize Theron (15 years younger), Minka Kelly (20) and Scarlett Johansson (24). And let’s not forget his brief marriage to Emily in Paris’s Leila George (gap: 32 years) that made him older than his own mother-in-law, actress Greta Sacchi. No-holds-barred Golden Globe host Nikki Glaser called Penn a “sexy leather handbag,” and since this 35-year dating gap is five years more than Nicov’s own age, Penn’s akin to an original ’84 Birkin.
Cher & AE Edwards: 40 years
Cher takes our age-gap cake and eats it too: For decades, the one-name-only songstress has been dating significantly younger (and always extra hot) men and not giving a damn what you think about it. Following a contentious divorce from the 11-years-older (and extra-controlling) Sonny Bono, Cher pivoted to date Val Kilmer (13 years younger), Tom Cruise (16) and “Bagel Boy” Rob Camilletti (18), whom she brought to the Academy Awards when she won her Moonstruck Oscar in 1988. Since then, Cher’s been turning back time even further with new boyfriend Edwards – he’s a full 40 years younger than the almost 80-year-old icon, but also a relatively mature 40 years old himself. Cher’s our all-time winner for forever inverting the gender age-gap stereotypes and embodying her famous quip to her mother’s advice to marry a rich man: “Mom, I am a rich man.” We kneel before our Queen.
