Aoki Lee Simmons, the 21-year-old daughter of Russell Simmons and Kimora Lee, is reportedly dating 65-year-old restaurateur Vittorio Assaf. A recently resurfaced clip appears to reveal that her parents had been forewarned.
Aoki’s relationship with Assaf was unveiled on April 5 after Page Six published photographs of the duo kissing on the beach while on vacation in Saint Barth’s earlier in the week. People quickly noted the 44-year age difference between Simmons and the much older restaurateur, and now an old clip of Aoki warning her father that she’d get a sugar daddy if he didn’t raise her allowance has made its way back to the public eye.
In the video, taken from an Instagram Live stream between Aoki and her father, Russell Simmons, last year, Russell and Aoki are debating raising the youngster’s allowance so that she can keep up with her model friends. Russell then takes a moment to let his youngest daughter know that he is very proud of her for recently landing a job.
“You’re going to work for a very important, distinguished gentleman,” said Russell. “I’m very proud of you for getting that job.”
The proud father goes on to uplift his daughter, telling her that she’s going to be a great servant to the world and make the world a better place.
“If you don’t raise my budget, I’m gonna get a sugar daddy,” laughed Aoki. As Simmons looked perplexed, Aoki said, “I’m kidding, I’m sorry. I’m kidding.”
“What’d you say?” asked Simmons, visibly stunned. “You don’t even have sugar daddy capabilities, right? Aren’t you a V? Of course you are, right?”
“I’m just saying,” she laughed. “If you don’t give me money, I’m gonna go, I dunno, sell… I’m gonna sell art.”
“Well…she wasn’t lying,” a commenter stated after the video was shared on Instagram by Onsite.
“Following in her mother’s footsteps,” noted another, a reference to the age difference between Aoki’s parents.
Kimora Lee, 48, and 66-year-old Russell Simmons are currently divorced. The former couple reportedly met when Kimora was 17 years old and still in high school. Simmons had founded Def Jam Recordings when he met Kimora as a rising model. The two were married in 1998 and had two children: Aoki, 21, and her 24-year-old sister, Ming.
Upon the breaking news of Aoki’s new relationship, the critics on X also couldn’t help but draw a parallel between the 21-year-old Harvard grad and her model mother.
“It’s a generational thing,” wrote one fan. “Kimora’s mother was fine with her dating an old man as long as he was rich and Kimora is fine with Aoki doing the same. A wasted Harvard degree.”
Lee and Simmons divorced in 2005 following years of Simmons’ alleged infidelities. They later wound up in a lengthy court battle after Simmons went into business with Lee and her now-ex-husband, investment banker Timothy Leissner. The three were in business together with Nu Horizons Investment Group, a company with shares in the calorie-burning drink Celsius.
Simmons filed a lawsuit in 2021 against his ex and Leissner. He claimed that Lee and Leissner used 4 million shares from the company to post bond in a criminal case in which Leissner was involved. The former Goldman Sachs banker pled guilty to criminal conspiracy in connection with his role in the 1MDB Malaysian sovereign fund international embezzlement scheme. Leissner agreed to pay $43.7 million into a compensation fund for victims. Lee countersued and argued that she did not have to inform Simmons about the shares because he’d resigned as manager of Nu Horizons back in 2018. The litigation remains unresolved.
Spectators online suggested that the ongoing legal troubles, coupled with the high cost of attending an Ivy League school, could have impacted her family’s finances — forcing Aoki to make good on her promise of getting a sugar daddy.
“Y’all surprised by Aoki Lee forget that she and her family are broke. Graduating from Harvard doesn’t erase that her father is trying to steal from them and her mother is forced to pay everything out of pocket. She’s dating that sun-burned gremlin because she needs a safety net,” said a commenter.
Amid the backlash and controversy, Simmons appears to be standing with his daughter’s decision. On April 6, one day after Aoki’s relationship went public, the father of two shared n image of himself with Aoki. He captioned the Instagram post, “Throw back from last fathers day nyc …bode bikram yoga express class .. vegan lunch cryotherapy vitamin drip … all around amazing day @aokileesimmons love you always.” The caption also included “im always waiting for any call any time” before being edited by the music mogul. The words “unconditional love” were also displayed on the photo.
Assaf is the founder of the Serafina Restaurant Group and the author of “Serafina: Modern Italian Cuisine for Everyday Home Cooking.” The divorced father of two has restaurants worldwide, including Serafina in New York City.
