Kimora Lee Simmons Speaks Out about Daughter Aoki's Brief Relationship with a Man 44 Years Her Senior

Aoki Lee Simmons was 21. He was 65. Their brief relationship drew attention in 2024. Now, Aoki's mother is sharing her perspective on a recent podcast.

She stayed silent when the headlines broke. Now, over a year later, Kimora Lee Simmons is speaking out, and she isn’t holding back about her daughter's brief relationship with an older man.

In a recent podcast interview, she shared how she found out, how quickly it unfolded, and why she felt it was a serious concern.

Aoki's Relationship Took Her by Surprise

In the December 9, 2025, episode of the "Not Skinny But Not Fat" podcast with host Amanda Hirsch, Kimora opened up about Aoki's 2024 relationship with 65-year-old restaurateur Vittorio Assaf.

At the time, Aoki was 21. The two had met while on vacation in St. Barths, a regular getaway for the Simmons family.

Kimora explained that she was completely unaware of the relationship until it became public. While she was familiar with Vittorio through her social circles and had known him for years as a restaurateur, she said she had no idea he was romantically involved with her daughter.

She also expressed discomfort with his reputation, hinting at past concerns without going into specifics, and acknowledged she was being cautious about what she could say publicly for legal reasons.

When Hirsch asked if she wanted to say, "What the hell are you doing?" to Aoki, Kimora replied:

"I didn't say it in that way because 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 that definitely was the thing."

The relationship escalated very quickly and caught her completely off guard, and Kimora learned about it at the same time the public did, which made the situation even more shocking for her.

Because the situation had become so public so quickly, Kimora felt unable to react the way a parent normally would in private.

The scrutiny made it impossible to deliver the usual motherly warnings or frustrations. Wanting to say things like "I told you so" or question her daughter's choices didn't feel appropriate given the timing and pressure surrounding the situation.

When Hirsch said, "She was going through it," Kimora nodded. Later, reflecting on the whole situation and her own history, Kimora didn't hold back. She explained:

"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."

Kimora described the relationship as very brief. She suggested it wasn't meaningful or serious and viewed it as nothing more than a passing moment.

A Look Back at Aoki Lee Simmons' Brief, Headline-Grabbing Romance

Reports of the romance initially surfaced in April 2024 when Page Six published exclusive photos of Aoki and Vittorio kissing on the beach during a getaway to St. Barths. The images quickly circulated online, sparking backlash and public curiosity.

Though Aoki shared videos on Instagram during the trip, referring to Vittorio as her "boyfriend" and calling him only the second serious partner she ever had, a source close to her later claimed the relationship had already ended. "It's 100% done. They're absolutely not dating," a source told the outlet.

According to the insider, Aoki insisted that she was never truly "with" Vittorio and dismissed it as something casual. Still, her posts at the time suggested otherwise.

In videos, she reportedly appeared cheerful and affectionate, showing off Vittorio's shoes, gushing about his height, and describing herself as the "happiest person to ever happy right now."

Those who know Vittorio weren't surprised by the pairing. According to another source, he has long been known for his attraction to younger women. They noted him as a "older man with little boy charm," adding that while he's aged, his preferences haven't changed.

Another person familiar with Vittorio from years ago suggested his appeal isn't only tied to wealth or status, hinting at physical attributes that drew women in.

Who Is Vittorio Assaf?

While much was said about his charm and dating history, Vittorio's public life paints a fuller picture. He is best known as the co-founder of the Serafina Restaurant Group, a popular international dining brand.

Born in Milan, he earned a degree in Political Science and later studied Law at the University of Urbino. Before entering the restaurant world, Vittorio worked for eight years on the floor of the Milan Stock Exchange and later transitioned into the fashion industry.

In 1985, he moved to New York and opened Café Candiotti, which featured original art by Andy Warhol and quickly became a celebrity hotspot.

Vittorio went on to create a global restaurant empire with locations in New York, Miami, Dubai, and beyond. He is known for his hands-on involvement with menu design and hospitality.

Where Is Aoki Now?

While her brief relationship with Assaf sparked headlines in 2024, Aoki has since shifted her focus and is now building a career in modeling. Though she graduated from Harvard, Aoki has been vocal about choosing fashion over more traditional academic paths.

In a 2022 TikTok video, she addressed criticism from those who questioned why someone with her education would enter an industry that doesn't require a degree. She explained that her decision wasn't about what she should do, but about what she loved doing.

Growing up, Aoki said she excelled in sports like volleyball because of her height, but that didn't mean she wanted to turn it into a career. To her, being good at something doesn't mean it has to define you, and struggling with something doesn't mean you can't pursue it.

She also pushed back against the idea that smart women can't be part of beauty, fashion, or creative spaces. "You can be two kinds of people in one person," she added. She urged her followers to stop questioning women who follow artistic passions simply because they're also academically accomplished.

People, she argued, should be free to do what makes them happy, whether that means using their degree, saving it for later, or not getting one at all. "Do whatever you want," she said. "And nothing is a waste of your talent."