The Moment
Kimora Lee Simmons is finally saying the quiet part out loud about daughter Aoki’s very public, very eyebrow-raising 2024 vacation fling with restaurateur Vittorio Assaf.
On a recent episode of the podcast “Not Skinny But Not Fat,” Kimora, 49, opened up about the brief romance between Aoki, then 21, and Assaf, then 65. She stressed that the two were never in a serious relationship and, in her words, only shared “a moment.”
Still, looking back, Kimora didn’t mince words. She straight-up called the age-gap situation “predatorial” and “kinda crazy,” saying it was “tough” to watch her daughter make what she framed as very public “mistakes.”
Kimora also revealed she’d known Assaf socially for years through the restaurant world and claimed his “reputation probably precedes him.” She says she found out about the fling at the same time everyone else did-when those beach PDA photos hit the internet-leaving her shocked and embarrassed.
And yes, she’s aware of the irony. Kimora herself once had a headline-making age-gap relationship: she met Russell Simmons when she was 17 and he was 35, a history she directly referenced while talking about why this situation bothers her so much.
The Take
I’m just going to say it: this is what happens when your kid’s “wild college phase” doesn’t stay on campus, it goes to St. Barts and ends up in paparazzi slideshows.
On one level, Kimora sounds like every mom who’s ever had to watch her grown child date a walking red flag. She talks about fighting the urge to scream, “What the hell are you doing?” and resisting the classic “I told you so.” That part is deeply relatable. The twist here is that the red flag in question was a man old enough to qualify for the senior discount, and the mom is a former teen bride who lived her own age-gap saga in full view of the culture.
Her use of the word “predatorial” is doing a lot of work. Legally, Aoki was an adult. But what Kimora’s really calling out is the power imbalance: a wealthy, well-connected 60-something zeroing in on a woman barely out of college, who also happens to be his friend’s daughter. Even if there was consent, it doesn’t mean the vibes weren’t off.
There’s a generational reckoning happening here. The kind of May-December relationship that used to be brushed off as “glamorous” or “eccentric” now gets put under a microscope, especially when the younger person is just old enough to rent a car in a few years. And when Mom has lived through a very similar dynamic, calling someone else “predatorial” hits like a confession and a warning at the same time.
What struck me most is that Kimora seems less angry at Aoki and more angry at the setup. She’s talked about feeling like her daughter was “set up,” about how no one expects their “toads” to be broadcast to the world. That’s the real nightmare of raising kids in public life: private bad choices become permanent internet tattoos.
If parenting in 2025 were a metaphor, this one would fit: it’s like watching your daughter learn to drive for the first time-but the car is on a highway, the dashboard is Instagram, and the whole world is in the back seat offering directions.
Receipts
Here’s what’s actually on the record and what’s just chatter.
Kimora Lee Simmons reflects on daughter Aoki’s ‘shocking’ fling with restauranteur 44 years her senior: ‘Predatorial’ https://t.co/PJz2tnotM5 pic.twitter.com/npMdd0J5Lm
— Page Six (@PageSix) December 9, 2025
Confirmed:
- On a recent episode of the podcast “Not Skinny But Not Fat,” Kimora Lee Simmons discussed daughter Aoki’s brief 2024 fling with restaurateur Vittorio Assaf, who was 65 at the time while Aoki was 21.
- Kimora stated on the podcast that the two were not in a serious relationship and described it as “a moment” rather than ongoing dating.
- She said she learned about the fling when the public did, after photos of Aoki and Assaf showing PDA on vacation circulated online in 2024.
- Kimora called the age-gap situation “predatorial” and “kinda crazy,” explicitly linking her opinion to her own past “big age gap relationship.”
- She confirmed she has known Assaf personally for years through his work as founder of a popular restaurant group and suggested his “reputation probably precedes him.”
- Kimora previously acknowledged feeling “embarrassed” by the photos and compared Assaf to a “toad,” while emphasizing that young women don’t expect every “toad” they kiss to go public.
- Kimora and Russell Simmons met when she was 17 and he was 35; they later married in 1998 and share daughters Ming and Aoki.
- In a 2024 video interview, Russell said that when it comes to Aoki’s romantic life, he can only offer “advice and unconditional love.”
Unverified / Reported:
- A social acquaintance previously described Assaf as an “older man with little boy charm” who has “always loved younger beautiful women” and whose “taste hasn’t changed” as he’s aged. These are character descriptions, not independently proven facts.
- Any implication that Assaf’s behavior is legally actionable has not been substantiated. Kimora herself hinted at legal sensitivity and framed her comments as opinion based on her experiences and observations.
Backstory (For Casual Readers)
If you’re not fluent in the Simmons family tree, here’s the quick catch-up. Kimora Lee Simmons became a fashion name in the late ’90s and 2000s, modeling and helming the Baby Phat brand. She married music mogul Russell Simmons, with whom she shares two daughters: Ming, now in her mid-20s, and Aoki, now 23.
In early 2024, photos emerged of Aoki on a beach vacation with restaurateur Vittorio Assaf, best known for co-founding a successful, celeb-favorite Italian restaurant group. The visuals-kissing in the ocean, cuddling on a boat-sparked instant commentary because of the 44-year age gap. Aoki was 21; Assaf was 65.
The internet did what it does: half the crowd scolded Assaf, half scolded Aoki, and the rest blamed the parents. Russell took a calm, “she’s grown, I just love her” approach. Kimora, meanwhile, made it clear she was embarrassed and uncomfortable, and now, months later, she’s putting firmer language-“predatorial”-to what many people were already thinking but tiptoeing around.
What’s Next
Practically speaking, this “romance” is already over. By Kimora’s own account, it never grew into a proper relationship, and there’s no sign Aoki and Assaf are still involved.
The bigger story now is reputational and generational. For Kimora, speaking so bluntly on a podcast suggests she’s done pretending this was just a cute little phase. She’s planting a flag: big age-gap relationships might have been normalized when she was coming up, but she’s not signing off on the same dynamic for her daughters.
For Aoki, this might become one of those early-20s chapters you spend the rest of your life explaining away with a laugh and a wince. She hasn’t, as of this writing, gone on a full public rehash of the fling-but she’s a savvy, media-literate young woman, so a future interview or social post addressing her side wouldn’t be surprising.
For the rest of us, the conversation Kimora just reopened isn’t going anywhere: When is an age-gap relationship simply unconventional, and when does it cross into “predatorial” territory, especially when fame, money, and family connections are involved?
One thing that’s important to note: there are no public allegations that any laws were broken here. What we’re looking at is a moral and emotional line, not a criminal one-and that gray zone is exactly why people feel so strongly about it.
Sources: Podcast interview with Kimora Lee Simmons on “Not Skinny But Not Fat,” released December 2025; celebrity news report summarizing her comments and the 2024 vacation photos, published December 9, 2025; archived 2024 video interview with Russell Simmons discussing his approach to Aoki’s dating life.
Where do you personally draw the line on age-gap relationships-does a pairing like 21 and 65 ever feel truly equal, or does the power imbalance make that impossible?
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