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Aoki Lee Simmons and her seasoned restauranteur boyfriend set the internet abuzz when tropical vacation photos of the May-December couple canoodling in St. Barts surfaced. 

On April 2, the 21-year-old model and daughter of former Def Jam founder Russell Simmons and Kimora Lee Simmons romped on the beach in St. Barts, sharing kisses with 65-year-old Vittorio Assaf while he snapped photos of Aoki. The typically private socialite openly flirted, swam, made out and bonded with Vittorio– to the chagrin of the internet. 

Users on the X app had plenty to say about the 44-year age gap between Aoki and Vittorio and the 21-year-old woman’s dating choice. 



Aoki and Vittorio posted pictures from St. Barts on social media. 

Clad in a multi-colored bikini top and barely-there solid bikini bottoms, the Ford Model Paris beauty struck a pose for the camera. 

“Girls (possibly mermaids!) on film 🎥😇🌊,” she captioned the post. 

Vittorio, the founder of Serafina Restuarant Group, uploaded a photo of himself and a homie of “25 years.”

The Milan-born restauranteur reportedly has a history of dating granddaughter-aged models. Vittorio has dated 24-year-old South Sudanese refugee-turned-high-fashion-model Nya Gatbel. He was involved in a scandalous split from his former wife of 20 years, Charlotte Bonstrom. The former model began an affair with her twin sister Cecilia’s husband during the pandemic. Charlotte was fed up with Vittorio’s thing for hot, young models, and she took her happiness into her own hands– at the expense of her twin sister. 

Aoki, a Harvard University graduate, also recently became the face of BCBG. The Blasian posted the good news on Instagram on April 3.


Trailblazing the way for the dressing of the contemporary women. A collection full of vibrant hues of fuschia to crimson, come with @AokiLeeSimmons and refresh your wardrobe.”

Here are some more images of Aoki at work. 


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