Aoki Lee Simmons is a Harvard graduate and model. She is the daughter of fashion model and mogul, Kimora Lee Simmons and hip-hop entertainment mogul, Russell Simmons. Naturally, she’s has been in the spotlight since birth; still, Kimora instilled within her a value for education that pushed her towards excelling academically.

Simmons developed a strong and genuine love for education, prompting her acceptance at Harvard Law. Aoki studied, worked, joined clubs, assisted professors and after declining several modeling gig offers, decided to get back out there. In celebration of her graduation, she took a trip with her boyfriend, who has left the internet in flames. Who is Aoki Lee Simmons, and who is her boyfriend, Vittorio Rassaf?

Who Is Aoki Lee Simmons?

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The 21-year-old model with a five-year plan likes to be prepared when she can. Simmons has been intentional about carving a lane out for herself, independent of her mother and father. She began modeling for her mother’s clothing line, Life in the Fab Lane, when she was just a toddler. Simmons then landed her first contract at the age of 13, an exclusive deal with Chanel.

Kimora had always emphasized the importance of education to her children, helping her daughter to develop a passion for it. The budding businesswoman graduated from high school at only 15 years old. She wasn’t allowed to go out on school nights: she went to school, played volleyball after school, came home, played the violin, did homework, ate dinner and went to bed.

This structure fueled her fire for acceptance into an Ivy League school. Once she became a student at Harvard, she also found, after declining multiple offers, that she was curious about returning to modeling. Simmons allowed it to influence some of her socioeconomic and cultural assignments, fusing her worlds. Once she graduated, she obtained a degree in Classics & Government and began prepping for the LSATs after graduation.

Aoki Lee Simmons Is Dating 65-Year-Old Restaurateur Vittorio Assaf

(Photo by Jared Siskin/Getty Images for Serafina)

Now, less than a year later, the former-student and current model is dating 65-year-old restaurateur Vittorio Rassaf. Vittorio is originally from Milan and co-owns a number of restaurants throughout the United States, the first of which he opened in New York City (called Serafina). After he and his wife of 20 years divorced, she went on to remarry her twin sister’s ex-husband. In the meantime, Vittorio joined the dating pool and was seen with Simmons, photographed on vacation while they laid on the beach. In another photo, the two can be seen sharing a kiss. When asked how he felt about the situation, Russell Simmons told TMZ that he won’t react negatively to her behavior. Instead, he plans to be around for advice and unconditional love. 

The hip-hop entertainment mogul was accused by a long list of women, of sexual misconduct in the 1980s, the 1990s and the 2000s. Post-rape accusation, Russell fled to Bali and then was seen in The Hamptons. He began dating Kimora when she was 17 and he was 35, marking an 18-year age gap between the two. Now, the 44-year-age-gap between that of Aoki and Vittorio is surfacing amongst headlines, breaking stories and deep dives into the ethics of their relationship.  

Is There A Double Standard In The Dating Age Gap?

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Kimora, the Baby Phat CEO and mother of five, is now married to Tim Leissner, an investment banker with whom she shares two children. While she and Russell are now divorced, there is an 18-year-age gap between them. A similar age gap exists between that of fellow pop culture subjects, Draya Michele and Jalen Green. The TV personality, model and mother of three is pregnant with the Houston Rocket shooting guard’s first child. Green has also tattooed Michele’s name on his abdomen. Their pairing has garnered outrage from men and women who deem their dynamic predatory. For years, even centuries, men of wealth have flaunted their desires for dating younger women. And it seems, no matter how criticized they may be, it’s never impacted how they’re viewed as a mogul or their level of success. 

Women, of any economic status, who date younger have often been categorized as “desperate,” unable to find a partner their own age. In any case, the safety of partners in their relationships matters above all else. Grooming, no matter the sex, has lasting effects described, via their artistry, as damaging by moguls and musicians. Taylor Swift and Demi Lovato are among the many figures in Hollywood who realized the impact of their relationships with older figures and the consistent themes of control and insincerity.

Not only has TikTok had a visceral response to the newfound love between Simmons and Rassaf, but her mother as well, being quoted by an inside source as “concerned to see her daughter in that kind of relationship due to what she herself went through.” While we have not heard from either party on the status and nature of their relationship, reports of their split are beginning to arise as the story only continues to plant a bigger seed of dialogue.