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Aoki Lee Simmons, 21, Slyly Asks Her 65-year-old Lover to Buy Her Expensive Jewelry, Watch as He Laughs Her Off

The controversy surrounding 21-year-old Aoki Lee Simmons, the youngest daughter of Kimora Lee and Russell Simmons, and Vittorio Assaf, a 65-year-old businessman, has reached new heights after the young Harvard grad shared an awkward video of her and her new beau. Now Aoki’s mother, Kimora, is seemingly weighing in.

The video was taken on the last day of Aoki Lee and Assaf’s St. Barth’s getaway. Aoki intended to shoot a vlog that included her boyfriend but did not show his face, as she wanted him to remain anonymous.

“I’m so sad [about leaving], but I’m very happy,” she shared in the clip as she talked to her 816,000 followers. “When I return home, everyone who knows me will be getting a happier, more chilled-out version of me.”

The footage continues as Aoki casually talks to Assaf, who is one year younger than her father. As the couple drives along the streets of St. Barths, they begin passing by a number of high-end stores, which prompts Aoki Lee to subtly hint that she’d like to be gifted some expensive jewelry from Bvlgari and Cartier.

“I am, though, a big Bvlgari person,” Aoki said as their car passes by the luxury boutique. Assaf seemingly ignores her, so Aoki repeats herself — this time louder.

Aoki Lee Simmons Is on Kimora's 'Last Nerve' as Her New 65-year-old Beau Laughs Off Hints for Lavish Gifts and Reveals Mary J Blige Had Her Eye On Him (Photos @aokileesimmons / Instagram ; @vittorioserafina / Instagram)
Kimora Lee Simmons (left) apparently is responding as daughter Aoki Lee Simmons (right, left photo) has taken to social media to flaunt her fling with wealthy restaurateur Vittorio Serafina (right). (Photos: @aokileesimmons/Instagram, @vittorioserafina/Instagram)

“I am, though, a big Bvlgari person,” she exclaimed. Once Assaf confirms that he caught her hint the first time, the young model tells him, “Okay, I just want to make that very clear,” before saying, “Bvlgari for me, bye Bvlgari,” in a playful voice.

But the hints did not stop there. “Hopefully, they have my necklace when I come back, and they don’t sell it to somebody else,” she quipped.

Soon after, Aoki spots the Cartier store out of the window.

“Oh, you know what I also like a lot?” she asks her new beau.

“What?” he asks, prompting Aoki to point at the Cartier store, “Cartier.”

Assaf, whose estimated net worth is $250 million, chuckles in amusement, completely ignoring his young girlfriend’s hints about designer brands.

Earlier in the clip, Aoki asks her new man, “Would you like to share your favorite thing about the trip, anonymously?” He answered, “To be with you.”

With her youthful giggle, she reiterated for her viewers, “He said me.”

Randomly, out of nowhere, Assaf brings a familiar name into the conversation.

“You know, Mary J. Blige wanted to be my partner?” he asked Aoki Lee as she shushed him and reminded him that she was recording a video.

She then redirects the conversation to ask Assaf if he’d like to accompany her on a trip to Kenya where she was invited by a friend. Assaf, confused, asks, “What?” before Aoki redirects the conversation again, “When are we going to Japan?”

“Japan is too much,” Assaf tells her.

“Baby, shush!” she hits back.

Commenters on social media could not hold back their disapproval upon seeing Aoki’s video.

“Not the Mary j bilge tea,” one person wrote.

But a few others believed people were being messy and that he meant Mary J Blige wanted to be a “business partner.”

A few people on Instagram commented on the model not-so-subtly name-dropping the designer brands.

“She sounds like a spoiled brat trying to get treats from her Granpa,” one person noted as another wrote, “Not her tryna convince him to take her shopping and he’s disregarding it I’m crying.”

Some people are simply concerned.

“Woah! This is NOT okay. This man is “triple” her age. Aoki Lee Simmons is 21yrs. old,” someone tweeted. “Vittorio Assaf is 65yrs old. She has a Sugar Daddy and tries to come off dominating the relationship. And she’s going to get herself hurt or worse if she’s not careful. Where’s Russell?”

The restaurateur has been paired with multiple high-profile women, including fashion model Nya Gatbel, who was 21 years old when they dated in 2021, and his ex-wife, 52-year-old Charlotte Bonstrom, with whom he shares two adult children.

(L - R) Daughter Valentina Assaf, Vittorio Assaf and son Vittorio Bonstrom (Photos @vittorioserafina / Instagram)
(From left) Daughter Valentina Assaf, Vittorio Assaf and son Vittorio Bonstrom. (Photos: @vittorioserafina/Instagram)

This love affair comes almost a year after the young woman playfully taunted her father during an Instagram Live that she would get a “sugar daddy” because they have her on such a tight budget.

As the news of her dating an older man hit the net, the celebrity father did not directly comment. Instead, he posted a tribute video to his beloved baby girl.

Russell Simmons shows his unconditional love to his daughter. @russellSimmons/ Instagram

“Throw back from last fathers day nyc …bode bikram yoga express class .. vegan lunch cryotherapy vitamin drip … all around amazing day,” the post captioned. “@aokileesimmons love you always”

While dad might not be weighing in, it seems that Kimora Lee Simmons, Aoki’s mama bear, has sent out a cryptic message about the budding romance.

The “Fabulosity” icon posted a video on her Instagram Story showing a mother panda bear gripping her cub firmly in her mouth and rushing to a platform. The mother, not being gentle, quickly flipped her cub over a wooden railing, leaving the cub dangling helplessly during the process.

Kimora Lee seems to weigh in on her daughter dating an older man. @kimoraleesimmons/Instagram

Over the clip, she wrote, “On my last nerve right now!”

But Aoki could be taking her cue in starting this May-December romance from Kimora.

Her mother and father formed an example of a generation gap relationship. Kimora was 18 when she started dating the Phat Farm founder. He was, at the time, 36, 18 years Kimora’s senior. Six years later, the two married. Their union would dissolve in 2008, with the divorce finalized the following year.

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