Kimora Lee Simmons didn’t get a private heads-up about her daughter’s love life before the internet did. Instead, the fashion mogul learned that Aoki Lee Simmons was dating a much older man at the exact moment the rest of the world caught on.
Speaking on the December 8 episode of Amanda Hirsch’s Not Skinny But Not Fat podcast, Kimora walked listeners through the surprise of realizing her 23-year-old daughter had sparked a brief romance with restaurateur Vittorio Assaf, who is more than 40 years her senior.
“It went from zero to 100 really quick,” Kimora said. “And I was like, ‘Aoki, I didn’t even know this was a thing.’” According to Kimora, the shock wasn’t just the relationship itself—it was how she found out. “I found out when the world found out,” she explained. “So that was what was so shocking.”
The photos that tipped everything off showed Aoki and Assaf packing on PDA while vacationing in St. Barths, a longtime Simmons family getaway. From there, the chatter escalated instantly.
Kimora admitted she had strong personal feelings about the age gap, shaped by her own lived experiences. “Having gone through—not exactly the same, but similar—that big age-gap relationship, let’s just call it that,” she said, “I do think it’s predatorial.”
Even so, Kimora was careful about how she addressed it with her daughter. “I didn’t say it in that way because it was this fast,” she said, snapping her fingers to emphasize the speed. “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.”
Ultimately, Kimora believes the relationship was fleeting. “I don’t even think that was a moment for them—or I should say the opposite,” she said. “I think it was just that: a moment. I don’t think it was anything else.”
The man at the center of that moment, Assaf, is the co-founder of the Serafina Restaurant Group, a well-known Italian dining brand with locations across New York and beyond.
According to People, Assaf grew up in Milan, studied law, and worked at the Milan Stock Exchange before moving to New York in the 1980s. He entered the restaurant world after opening Café Candiotti and later launched Serafina in 1995 alongside Fabio Granato.
Despite the headlines, the romance ended almost as quickly as it became public, with sources confirming the pair split within days.
For Kimora, the situation reinforced a reality she knows well as a public figure and parent. “That’s the whole thing we were saying about living out your life in public,” she said. “I think that’s very, very, very tough.”
