Over the weekend, Page Six published tons of photos of Aoki Lee Simmons in St. Barts with her new boyfriend, a 65-year-old man named Vittorio Assaf. Assaf is the co-founder of Serafina (the restaurant chain) and he apparently has a home in St. Barts. Judging from Aoki’s social media, it definitely seemed like this was some kind of sugar daddy situation, but Aoki’s mother Kimora managed to do some cleanup on the gossip. People Magazine reported that Aoki and Vittorio were absolutely dating, and it wasn’t like Aoki just flew to St. Barts with some rich older man as some kind of quid pro quo. Well, right after all of that People Mag cleanup, Aoki’s friends let it be known that Aoki is no longer dating Assaf.
Kimora Lee Simmons is furious about her daughter’s new romance with Serafina founder Vittorio Assaf, who’s 43 years her senior, according to sources. But we’re told Aoki Lee Simmons’ worried mom need not fret — because it’s already over!
It turns out the model’s PDA-filled getaway with the 65-year-old restaurateur was just a fling.
“It’s 100% done. They’re absolutely not dating,” a source close to Aoki told Page Six.
Then again, Simmons referred to Assaf as her “boyfriend” multiple times during the Instagram Live videos she posted from their romantic St. Barts vacation. In one clip, the 21-year-old even revealed he’s the “second boyfriend” she’s ever had while taking her followers on a tour of his St. Barts property.
After Page Six posted exclusive pics of the pair smooching on the beach, the source told us Aoki said, “Of course, I’m not with him. I was never with him,” when they spoke to her on Monday.
Still, Aoki appeared more than happy to vacation with the restaurant whiz at his island home. “I’m the happiest person to ever happy right now,” she said via social media while giving the house tour. At one point, she even showed off his shoes, saying, “Look at how huge his shoes are. That makes me really happy. He’s [6-foot-4],” she gushed.
A source, who knows Assaf, described him as an “older man with little boy charm.”
“He’s always loved younger beautiful women. He’s gotten older, but his taste hasn’t changed,” the insider said. “I wouldn’t be surprised if he’s out with another young girl tonight!” they added. Another source — who is Aoki’s senior by decades and told us they slept with Assaf many years ago — added that one reason women fall for him is thanks to his impressive endowment, and they don’t mean financially! “It’s the biggest… in New York,” the insider, who was surprised he was with someone as young as Aoki, said.
Despite video clips of Aoki boasting about wanting gifts from stores like Bulgari and Cartier, the source said she’s not materialistic and it’s all “absurd.”
“She’s not even like that. She doesn’t care about jewelry. She doesn’t have Hermes. It’s not even her. She doesn’t even care about expensive things like that. She’s like more of a geek,” the source said.
Yeah, when you’re frantically telling people “I’m not even really dating that guy, I swear, I’m not even materialistic, I’m such a nerd,” you should probably just quit while you’re ahead. My feeling is just own it, especially if you’re showing off your sugar baby lifestyle on social media. You don’t have to reinvent the wheel on this one, it really has happened many, many times before. Everybody does dumb sh-t and it sucks that it’s all playing out in Page Six, but honestly, Aoki should have put down her phone. I hate how many of these younger women are trying to make escorting or sugar dating into a curated influencer lifestyle.
Who is Vittorio Assaf? Meet the Serafina co-founder seen kissing Aoki Lee Simmons https://t.co/l4FzwdjaTB pic.twitter.com/qO2qijbIvR
— Page Six (@PageSix) April 5, 2024
Russell Simmons's daughter Aoki Lee Simmons, and her alleged 65-year-old boyfriend Vittorio Assaf pic.twitter.com/Q8GXEO2wi0
— WORLDSTARHIPHOP (@WORLDSTAR) April 8, 2024
Photos courtesy of Cover Images.
-
- HollyRod 2023 DesignCare Gala at The Beehive. Featuring: Aoki Lee Simmons Where: Los Angeles, California, United States When: 16 Jul 2023 Credit: Faye’s Vision/Cover Images
-
- HollyRod 2023 DesignCare Gala at The Beehive. Featuring: Aoki Lee Simmons Where: Los Angeles, California, United States When: 16 Jul 2023 Credit: Faye’s Vision/Cover Images
“Look at how huge his shoes are that makes me really happy “. OMG.
Good grief, that part. At 21 you wouldn’t have caught me dead with a 65 year old. All shades of ick really…
YUUUUUUUUCCCCKKK! The ick is strong on this whole story!!
Maybe everyone can stop the pearl clutching now haha
But yeah happy to hear it was just a quick “fling” and there wasnt anything more sinister about it. (other than the obvious ick factor)
Aoki herself called him her boyfriend in her manic videos that she posts. Now she’s pretending it was just a fling
OMG this is so much messier than it needed to be. She should have just owned it – he’s so much older but he’s so interesting and fun and she’s just meeting great people, not looking to get married right now, etc. Lying about calling him her boyfriend in videos of his closet is weird.
My guess is that he likely dumped her. Most older wealthy sugar daddies don’t want their “relationships” with very young women blasted all over social media, esp if negative publicity and/or public backlash could affect their businesses. And this was all over social media with a lot of people mocking them. She’s young, hopefully she has learned from this experience. It is concerning that these young ladies put so much of their personal lives on social media.
Didn’t comment yesterday, but much older man is the sort of stupid you can fall into when young. Some of the best advice I got when young is that people get into trouble either through lust or curiosity, so recognize your danger zone.
Looks like Aoki is a fellow curiosity girlie.
I think there are young women who get involved with misogynistic and grooming, older men, and that situation is absolutely damaging to them later on in life. And there are plenty of young women who get involved with older men because they like the lifestyle and the attention and the gifts and, once it runs its course, the woman is over it without any damage except for a fun story. The problem that makes a lot of older women who have seen this play out worry for the young women in this situation is that they aren’t going to know which situation they’re in until the damage is already done. I am glad that Aioki’s fling is the second type.
In other commentary, I find her face to be so interesting. In some angles, specially in that top picture where she’s smiling, her face looks kind of awkward. But in other angles like the second green outfit and the on the beach, she’s just absolutely gorgeous. I kind of love that because it reminds me of something I think Coco Chanel said, which is that no woman can truly be beautiful who is not also sometimes truly ugly. I totally notice that myself some days when I look in the mirror and I’m like I am a Smokeshow. other days, I think I could not be more ugly. It’s just like some days, my face blends together a little bit better and I have no idea why.
My first boyfriend (French too) said this… a truly beautiful person can also be ugly…. Now I know where he got it from…
When I see her face all I see is her dad. Too bad she did not get more of her mothers look
Aoki looks a lot like one of my childhood friends and because of that, I find myself weirdly always rooting for her.
Interestingly, her sister, Ming Lee, is “prettier” at first appearance, but I used to watch Kimora’s show, Fabulosity (or whatever it was called) and Aoki was always much more charismatic on screen. She was a performer and creative and it absolutely showed, even when she was a child (and even though she looks more like her father).
She wants to be in the industry and is already working as a model. I hope this doesn’t derail her career and she can use it to boost her brand. I hope she also gets some media training and gets more skillful about what she shares and how she talks about it. She doesn’t owe anyone any explanations about her personal life, but if she’s going to be dating old ass men, she should work on her “Yes, and?” vibes.
I keep wondering if Kimora knew Aoki was dating an old ass man and what Aoki had said about her trip.
From her vid that CB posted yesterday, I found it a bit alarming, not about the age difference, but about his call to “check on” her.
It’s the first time I saw her in video; she has such a unique, animated, beautiful face. More stunning than pictures.
Girllllll. No. Why????! Look at his shoes all day he’s still going to be 50 yrs older than you ankles up. Just no.
Oh wow, Kimora put a big fat lid on it. I have a lil respect for that kind of mommy-ing.
Yeah, Kimora left home and traveled on her own internationally as a model at 14/15 years old. (There’s an old interview clip of her talking about that and returning home to go back to school in between fashion shows – her mother couldn’t afford to leave her job and travel with her so she was by herself).
Kimora knows how these old men operate as well as the media and can guide Aoki.