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Kimora Lee Simmons reflects on daughter Aoki’s ‘shocking’ fling with restauranteur 44 years her senior: ‘Predatorial’

December 9, 2025
in News
Kimora Lee Simmons reflects on daughter Aoki’s ‘shocking’ fling with restauranteur 44 years her senior: ‘Predatorial’

Kimora Lee Simmons called her daughter Aoki Lee Simmons’ brief romance with much older Vittorio Assaf“predatorial.”

Simmons spoke candidly about the headline-making 2024 fling — during which Aoki was 21 while the restauranteur was 65 — and how “tough” it is to watch her daughter make public “mistakes.”

Kimora noted the two were not seriously dating and only shared “a moment” together during her appearance on the “Not Skinny But Not Fat” podcast dropping Tuesday, per People.

She also shared that she knew Assaf — who’s the founder of Serafina Restaurant Group — before he started dating Aoki, who’s now 23.

Kimora Lee Simmons and Aoki Lee Simmons at the Dior Men's Spring/Summer 2023 Collection.
Kimora Lee Simmons reflected on her daughter Aoki briefly dating restauranteur Vittorio Assaf in 2024 on the “Skinny But Not Fat” podcast. Getty Images,
Serafina restaurant founder Vittorio Assaf holding a large focaccia bread.
Aoki was 21 years old at the time, while Assaf was 65. vittorioserafina/Instagram

“I know this guy growing up myself. He’s a restauranteur,” she said. “I don’t know, I don’t want to get into troubles legally but I think his reputation probably precedes him.”

The mother of five said she found out Aoki was dating Assaf “when the world found out” and admitted she was shocked.

“I’ve learned all these crazy things. You can’t give the, ‘I told you so,’ right now,’” she said about her mindset at the time. “You can’t give the, ‘What the hell are you doing’ right now. You can’t give those things right now.” 

Looking back, Kimora called the romance “predatorial.”

Aoki Lee Simmons at the American Ballet Theatre Spring Gala.
Kimora said it was “tough” to watch Aoki make her own “mistakes” in public. Getty Images for American Ballet Theatre
Vittorio Assaf holding a large bottle of liquor and a guest holding oversized scissors.
Kimora called the shocking romance “predatorial.” Getty Images for Serafina Madison

“I feel like and having gone through not exactly the same but similar…that big age gap relationship, let’s just call it that. I do think it’s predatorial,” she said. “… I think that’s predatorial and kinda crazy.” 

Kimora met her first husband, Russell Simmons, in 1992 when she was 17 and he was 35.

Kimora and Russell, who were married from 1998-2009, share Aoki as well as daughter Ming, 25.

A source, who knows Assaf, described him to Page Six last year as an “older man with little boy charm.”

Vittorio Assaf gives a thumbs up while holding a drink at the Southampton Fresh Air Home's auction benefit gala.
The mother of five also said she knew Assaf before he started dating Aoki, and that his “reputation probably precedes him.” Joe Schildhorn/BFA / Shutterstock
Kimora Lee Simmons and Aoki Lee Simmons pose together at Teen Vogue Summit 2023.
Kimora previously likened Assaf to a toad and said she was embarrassed by her daughter Aoki’s headline-making PDA pics with him in St. Barts. Getty Images for Teen Vogue

“He’s always loved younger beautiful women. He’s gotten older, but his taste hasn’t changed,” the insider said.

Russell didn’t appear stressed over the May-December romance at the time, telling TMZ last April of his youngest daughter, “All I can do is offer my advice and unconditional love.”

Meanwhile, Kimora admitted to the outlet a month later that she was “embarrassed” to see the PDA pics of Aoki and Assaf — whom she likened to a toad.

“She’s a young pretty girl, and I think, we don’t think the toads we may kiss is going to be broadcasted,” she shared. “And I personally feel a little bit like she was set up, which is why I try to teach the girls. There’s definitely an age dynamic there.”

The post Kimora Lee Simmons reflects on daughter Aoki’s ‘shocking’ fling with restauranteur 44 years her senior: ‘Predatorial’ appeared first on Page Six.

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