Kimora Lee Simmons Breaks Silence On Daughter Aoki Lee's 'Shocking' Fling With 44 Years Older BF

Aoki Lee’s romantic spree with a man more than twice her age was one of the hottest celebrity stories in 2024 that had set off a firestorm of headlines and debates. Aoki, who was only 21 years old last year, set the tabloids abuzz from the moment she was spotted with Vittorio Assaf, a 65-year-old restaurateur whom she had met in St. Barths. With a glaring age gap of 44 years, fans were curious to know what Aoki’s parents thought about the eyebrow-raising relationship.

And now, her mom, Kimora Lee Simmons, is finally speaking out about how she felt about Aoki’s viral romance with a man old enough to be her grandfather. Calling her reaction 'disappointed' doesn’t come close, but Kimora chose to bite her tongue for a very specific reason.

Kimora found out about Aoki’s romance when the world did

Recently, the fashion mogul appeared on the Not Skinny But Not Fat podcast with host Amanda Hirsch, where she finally addressed daughter Aoki’s brief but viral fling. In the December 8, 2025 episode, she revealed she learned about Aoki and Vittorio’s romance the same way everyone else did: through their PDA photos in St. Barths. Recalling the shock of seeing her young adult daughter kissing the restaurateur, whom she had known growing up, Kimora said:

“It was this fast, 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 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. So that was what was so shocking.”

Kimora calls the relationship ‘predatorial’

The photos, showing Aoki kissing the 65-year-old founder of the Serafina Restaurant Group in St. Barths, went viral on social media in April 2024. And while fans were shocked, Kimora says she was equally blindsided by this unexpected turn of events. Speaking about it now, she didn’t sugarcoat things when asked how she felt about the massive age gap.

Reflecting on her own dating past, where she herself has dated older men, the Waist Deep actress had nothing else to describe Aoki and Vittorio’s romance as ‘predatorial’. She said:

“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… But I do think in general, of those kinds of things… 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.”

Kimora herself has been no stranger to unconventional romances. She was only 23 when she married her ex-husband and Aoki’s father, Russell Simmons, who was 41 at the time. Though she parted ways with the hip-hop icon in 2009, she has been candid in recent years about re-examining that chapter of her life and rethinking her decisions. 

When discussing how she felt about a much older restaurateur pursuing her daughter, Kimora made it clear she wasn’t fond of Assaf, noting she actually knew him from the New York social scene. She hinted at a reputation he carries, stopping herself before saying more for legal reasons. The actress shared:

"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. I know this guy growing up myself. He’s a restaurateur. I don’t know, I don’t want to get into trouble legally, but I think his reputation probably precedes him. Is that okay to say legally?”

Why didn’t she confront Aoki immediately?

While she was undeniably taken aback upon knowing of Aoki’s relationship, Kimora chose not to step in and let her daughter learn from her own mistakes. Aoki, who had just recently graduated from Harvard at 20, was no stranger to the public scrutiny that came with celebrity fame. And Kimora believed the best way to guide your kids was to avoid embarrassing them further when the world was already watching:

“I let my kids make their own mistakes... That’s the whole thing we were saying about living out your life in public, and I think that’s very, very, very tough. 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."

What happened to Aoki’s questionable fling?

Aoki and Vittorio’s romance flizzled as quickly as it started. After setting off a tabloid firestorm in April 2024 with their kiss and other PDA-filled moments, the relationship died down, allegedly within barely a week, with sources telling PEOPLE:

"Not only is it 'over', it was never a thing. 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."

The romance has long fizzled, and Aoki, now 23, appears focused on modeling and activism. Meanwhile, Kimora continues raising her blended family of seven, including daughters Ming and Aoki with Russell Simmons, son Kenzo with Djimon Hounsou, and two younger sons, Gary and Wolfe.

Read Next: 'Domenica Montero' Premiere: Where To Watch The First Episode Of Angelique Boyer's Telenovela?

AWESOME NEWS! Now you can download BollywoodShaadis app and never miss a story. Get App

AWESOME NEWS! Now you can download BollywoodShaadis app and never miss a story. Choose your device Android or IOS (Apple)