Aoki Lee Simmons, 21, Sparks Controversy with New 65-Year-Old Boyfriend Vittorio Assaf

The internet is abuzz with responses on the unexpected love affair between 21-year-old model Aoki Lee Simmons and a 65-year-old Italian restaurateur, Vittorio Assaf. The couple has a 44-year age gap, and they were recently seen cuddling and kissing at the beaches of St. Barts.

Who is Aoki Lee Simmons?

Aoki is Kimora Lee Simmons, 48, fashion mogul mother and Russell Simmons’,66 businessperson, youngest child. She followed her mom’s footsteps by working as a model for brands like Baby Phat, Just Fab from infant time. Aoki made her runway debut for Pyer Moss Paris Couture in 2021 and has graced the covers of magazines like Teen Vogue among others.

Aoki’s academic success can be added to her emerging modeling career. In 2023 she graduated from Harvard University at just 20 years old. Talking about criticism faced by Aoki for pursuing modelling despite being through an Ivy League education she said “I’d like to change the notion that you cannot be smart and pretty or smart and appreciate your outward appearance or have a beauty creative fashion based occupation”.

Who is Vittorio Assaf?

Vittorio Assaf who was born in Italy in 1956 is widely recognized as one of the co-founders of Serafina restaurant chains. This business venture was initiated after his friend Fabio Granato barely survived a near-death experience caused by getting lost at sea; it led them to their mission of offering outstanding Italian pizza & pasta worldwide.

Assaf has been able to expand Serafina across three continents having dozens of locations under his leadership. However, his personal life underwent some turmoil over recent years. In relation to Charlotte Bonstrom, Assaf’s spouse for more than two decades, she left him in 2021 following an affair with her twin sister’s husband himself. Now the ex-partners have two kids.

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Reaction to Aoki and Vittorio’s Romance

Their relationship came under fire from online users when they learned about it in a report; the majority was afraid of the big age difference between them. Aoki’s Instagram had one comment saying, “A 65 yr old man? Blink once for help. Twice and we’ll send the cops.” Another commenter wrote, “Girl that man is an old creep. You’re too smart and beautiful to fall for such a classic pattern.”

However, Aoki has not been bothered by critics. On her Instagram story she posted, “Errr well now I know why folks were calling me.” It seems she was reacting to photos that had leaked out. She met Vittorio in St Barts stated a close source of her that added they are “having fun together” according to People magazine which is a favorite place for Simmons family during holidays.

It has been observed though that Russell Simmons, Aoki’s father himself, is also close in age to Vittorio at 66 years old. However, Aoki doesn’t seem to have a good relationship with him as she did before anymore. She publicly called out her father back in 2023 blaming him for how he mistreated both herself and sister highlighting texts being exchanged between them which were alarming giving her panic attacks and harassing my friends accusations.

The Controversy of Celebrity Age Gap Relationships

There have been many celebrity couples with significant age differences including Aoki Lee Simmons’ romance with Vittorio Assaf which is just another example of this trend. One recent example includes model Draya Michele who dated NBA player Jalen Green who was only 22 at the time while Draya Michele herself was already 38. Scott Disick on his part has been dating much younger women several times unlike his current girlfriend Amelia Hamlin who is just twenty years old.

Caution is advised by relationship experts that while age gap relationships may work, they are faced with distinctive challenges. “The greater the age difference, the more likely you will have differences in your goals, desires and values,” asserted therapist Rachel Sussman to Women‘s Health. Disparities between people’s ages can lead to imbalances of power and difficulties in communicating effectively.

However, every relationship has its own unique aspect, therefore what counts is not so much a number but the people involved. “You can have a big age gap and have a healthy relationship or you can have a small age gap and have an unhealthy relationship,” Sussman says. Sharing the same values, showing mutual respect and having open communication are what matters most.


The news surrounding Aoki Lee Simmons’ new romance with Vittorio Assaf highlights how society remains both fascinated and troubled by extreme age differences in relationships. For instance, critics worry about Aoki’s youngness as well as the forty-four-year span between her and her boyfriend. Meanwhile, supporters argue that only Aoki and Vittorio know what makes their love strong enough in real sense of it. While they continue to date only time will tell if they make it through their story together for public consumption One thing is clear- Their union has ignited important conversations around dating dynamics, power relations, and challenging societal norms of relationships.

Alexander Brown

Alexander Brown is a seasoned entertainment journalist with a keen eye for the latest celebrity happenings. With years of experience in the industry, Brown brings insightful analysis and captivating storytelling to every piece. From red carpet events to exclusive interviews, he delivers the juiciest news and updates on your favorite stars. Stay tuned to Brown's blog for the inside scoop on all things celebrity.

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