Kimora Lee Simmons
IG /babyphat

Kimora Lee Simmons has broken her silence on daughter Aoki Lee Simmons' brief romance with a man 44 years her senior, branding the relationship 'predatorial and kinda crazy' in a candid podcast interview.

The Baby Phat founder appeared on the Not Skinny But Not Fat podcast with host Amanda Hirsch, where she addressed her daughter's headline-making fling with restaurateur Vittorio Assaf. The 65-year-old founder of the Serafina Restaurant Group was spotted with then-21-year-old Aoki during a trip to St Barths in April 2024.

Simmons revealed she was blindsided by the pairing, learning about it at the same time as the rest of the world when paparazzi photos of the pair showing PDA began circulating online.

'It went from 0 to 100 really quick, and I was like, Aoki, I didn't even know this was a thing,' she admitted. 'I found out when the world found out. So that was what was so shocking.'

Kimora Lee Simmons Reflects on Her Own Age Gap History

The mother of five drew from personal experience when assessing the situation. Simmons met her first husband, hip hop mogul Russell Simmons, in 1992 when she was just 17 and he was 35. The pair married in 1998 and divorced in 2009, sharing daughters Ming, now 25, and Aoki, now 23.

'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,' Simmons told Hirsch. 'I think that's predatorial and kinda crazy.'

The entrepreneur also revealed she knew Assaf before the relationship surfaced. 'I don't want to get into trouble, legally, but I think his reputation probably precedes him,' she said. A source previously told Page Six that Assaf was an 'older man with little boy charm' who has 'always loved younger beautiful women'.

Why Kimora Stayed Silent During the Public Fallout

Simmons explained she resisted the urge to publicly criticise her Harvard-educated daughter at the time. Aoki, who was accepted to the prestigious university at just 16 and graduated in 2023, found herself at the centre of intense media scrutiny when the photos emerged.

Simmons said she knew better than to confront her daughter in the heat of 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. 'But that definitely was the thing.'

At the time, Simmons did not hold back entirely. She told reporters she was 'embarrassed' by the PDA photographs and likened Assaf to a 'toad', suggesting her daughter had been 'set up'. Aoki's father Russell took a more measured approach, telling TMZ he could only offer 'advice and unconditional love'.

Aoki Lee Simmons Romance With Vittorio Assaf Ended Quickly

The relationship proved short-lived. Just four days after People confirmed the pair were spending time together, a source close to the Simmons family said they had already parted ways.

'Not only is it over - it was never really a thing,' the insider said at the time.

Simmons now views the episode as a fleeting moment rather than a meaningful relationship. 'I don't even think that was a moment for them - or I should say the opposite,' she shared. 'I think it was just that: a moment. I don't think it was anything else.'

The fashion mogul said she tries to let her children learn from their own experiences, though she acknowledged the difficulty of watching them navigate public mistakes. 'That's the whole thing we were saying about living out your life in public,' she reflected. 'I think that's very, very, very tough.'

Simmons is also mum to sons Kenzo, 16, with actor Djimon Hounsou, Gary, 15, whom she adopted in 2020, and Wolfe, 10, with ex-husband Tim Leissner.

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