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BY Dollita Okine, 3:52pm December 10, 2025,

Kimora Lee Simmons finally speaks out about the time her daughter Aoki dated a man 44 years her senior

by Dollita Okine, 3:52pm December 10, 2025,
Photo credit: Instagram, Kimora Lee Simmons

Entrepreneur Kimora Lee Simmons recently discussed her true feelings about her daughter, Aoki Lee, dating a significantly older man in April 2024. 

In a preview of the Tuesday, December 9 episode of the Not Skinny But Not Fat podcast, shared exclusively with People, Simmons told host Amanda Hirsch about her reaction to her then-21-year-old model daughter’s relationship with then-65-year-old restaurateur Vittorio Assaf, whom they met in St. Barths.

“What was your reaction to that in real time?” Hirsch asked. 

“I let my kids make their own mistakes, like I said. That’s the whole thing we were saying about living out your life in public, and I think that’s very, very, very tough,” Simmons explained. “I don’t even think that was a moment for them, though. Or I should say the opposite. I think it was just that — a moment. I don’t think it was anything else.”

READ ALSO: Aoki Lee Simmons to quit modeling after being told she’s ‘not pretty enough’, compared to mom Kimora

“I don’t even know…first of all, I know this guy. But I didn’t know this guy in that capacity like with my kid or that you were even dating my kid,” she continued. “I know this guy growing up myself. He’s a restauranteur. I don’t know, I don’t want to get into troubles legally but I think his reputation probably precedes him. Is that okay to say legally?”

Assaf, who founded the Serafina Restaurant Group, encountered Aoki  while on holiday in St. Barths, a location frequently visited by the Simmons family.

“Were you like, ‘What the helly are you doing to Aoki,’ or no?” asks Hirsch,

“I was, but I didn’t say it in that way because it was this fast,” Simmons stated. “And it blew up to be so much, so then you can’t be the mom that’s like, ‘What the hell are you doing?’ But that definitely was the thing.”

“But it went from 0 to 100 really quick, and I was like, ‘Aoki, I didn’t even know this was a thing.’ I found out when the world found out,” the mom of five remarked. “So that was what was so shocking. And you can’t say as a mom, and I’ve learned all these crazy things. You can’t give the, ‘I told you so,’ right now. You can’t give the, ‘What the hell are you doing’ right now. You can’t give those things right now.” 

“She was going through it,” Hirsch said.

“Yeah, it was a lot,” Simmons responded. “It was a lot. But I do think in general, of those kinds of things, 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. We said all of that to get to what Kimora thinks about it. I think that’s predatorial and kinda crazy.” 

READ ALSO: Kimora Lee Simmons talks about being a ‘surrogate mom’ to Diddy’s twin daughters

A source close to the Simmons family revealed that Simmons’ daughter and Assaf went their separate ways just four days after People verified they were dating.

“Not only is it ‘over’, it was never a thing,” the insider told People. “Aoki is learning to navigate her private life in a public sphere. And that can be difficult. However, Kimora was concerned to see her daughter in that kind of relationship due to what she herself went through.”

In contrast to his ex-wife’s reported reaction, Aoki’s father, Russell Simmons, seemed unfazed by the age-gap relationship, as he told TMZ last April that he could only offer his “advice and unconditional love” regarding his youngest daughter’s “May-December romance,” according to Page Six.

READ ALSO: Russell Simmons’ daughter Aoki, 21, is reportedly dating wealthy 65-year-old restaurateur Vittorio Assaf

Last Edited by:Kofi Oppong Kyekyeku Updated: December 10, 2025

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