New York, December 9, 2025 – Kimora Lee Simmons has described her daughter Aoki Lee Simmons’ short-lived 2024 romance with 65-year-old restaurateur Vittorio Assaf as “predatorial,” speaking openly about the pain and powerlessness she felt watching the very public fling unfold when Aoki was only 21.
In a preview clip from Tuesday’s episode of the “Not Skinny But Not Fat” podcast, the 50-year-old fashion mogul and mother of five reflected on the whirlwind relationship that dominated headlines last spring. “I feel like… 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,” Kimora said. “I think that’s predatorial and kinda crazy.”
The romance began during a family trip to St. Barths in April 2024. Aoki, then 21 and freshly graduated from Harvard, was photographed kissing and cuddling with Assaf, the Italian-born founder of the upscale Serafina Restaurant Group, on the beach. The 44-year age gap instantly sparked global backlash and endless memes, with the images going viral within hours.
Kimora admitted she found out about the relationship the same way everyone else did — when the paparazzi photos hit the internet. “It went from 0 to 100 really quick,” she told host Amanda Hirsch. “I was like, ‘Aoki, I didn’t even know this was a thing.’”
She revealed she had known Assaf for years through New York’s restaurant scene. “I know this guy growing up myself. He’s a restaurateur,” she said, choosing her words carefully before adding, “I don’t want to get into legal trouble, but I think his reputation probably precedes him.”
Despite her shock and private concerns, Kimora said she consciously held back from scolding her daughter in the moment. “You can’t give the ‘I told you so’ right now. You can’t give the ‘What the hell are you doing?’ right now,” she explained. “I’ve learned all these crazy things… you have to let them make their own mistakes, especially when everything is so public.”
The fashion icon was especially embarrassed by the explicit PDA photos. “She’s a young pretty girl, and I think we don’t think the toads we may kiss are going to be broadcasted,” she previously told People magazine in May 2024. “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.”
Kimora’s strong language carries added weight because of her own history. She met Russell Simmons in 1992 when she was 17 and he was 35 — an 18-year gap. The couple married in 1998, had daughters Ming (now 25) and Aoki, and divorced in 2009 after a turbulent marriage. Though Kimora has long credited Russell with helping launch her career, she has also spoken candidly in recent years about the complexities and power imbalances of entering such a high-profile relationship as a teenager.
The St. Barths fling ended almost as quickly as it began. Sources close to the family insisted at the time that “it was never a serious thing — just a moment.” Aoki, now 23, has since returned to modeling (walking for Saint Laurent and starring in campaigns) and her academic pursuits in Japanese literature, rarely addressing the episode publicly.
For her part, Kimora said the experience reinforced her approach to parenting adult children in the public eye. “That’s the whole thing about living out your life in public,” she told Hirsch. “You have to let them learn.”
The candid conversation arrives as Kimora continues to rebuild her Baby Phat empire and navigate life with her blended family of five children: Ming and Aoki with Russell Simmons, Kenzo (16) with actor Djimon Hounsou, Gary (15) with ex-husband Tim Leissner, and adopted son Wolfe (10).
As the full podcast episode drops today, Kimora’s unflinching take — calling out predatory dynamics while acknowledging her own past — has already struck a chord with listeners who see it as both a protective mother’s warning and a powerful moment of generational reflection.
