Kimora Lee Simmons' daughter Aoki Lee Simmons, 21, kisses millionaire restaurateur, Vittorio Assaf, 65, during loved up holiday to St.Barts

Kimora Lee Simmons and Russell Simmon's daughter Aoki Lee Simmons, 21, was spotted kissing restaurateur Vittorio Assaf, 65, in St. Barts earlier this week.

Aoki and Vittorio, who is a father of two, share a 44-year age difference. 

The model was seen sharing passionate kisses with the Italian-born Vittorio, who is the founder of the Serafina Restaurant Group, during the beach vacation together, according to Page Six.

Vittorio shares two children with ex-wife Swedish model Charlotte Bonstrom, 53: son Vittorio, 21, and daughter Valentina, 17.

'Aoki and Vittorio are spending time together and enjoying each others' company,' a source told People magazine. 

The insider also noted that St.Barts is a favorite vacation spot for the Simmons family. 

Hours after they were pictured smooching on the beach, Aoki appeared to address the romance rumors on her Instagram page, sharing a snap of herself with the caption 'Err well now I know why folks were calling me,' which she soon appeared to delete. 

Aoki is a model and a graduate of Harvard University; she got her degree at age 20 (in 2023), having been accepted into the prestigious school at age 16. 

Kimora Lee Simmons and Russell Simmon's daughter Aoki Lee Simmons, 21, was spotted kissing restaurateur Vittorio Assaf, 65, in St. Barts earlier this week

Hours after they were pictured smooching on the beach, Aoki appeared to address the romance rumors on her Instagram page, sharing a snap of herself with the caption 'Err well now I know why folks were calling me,' which she soon appeared to delete 

Aoki, 21, pictured with her mother, Baby Phat founder Kimora Lee Simmons, 48

In the images obtained by the outlet, Vittorio was seen kissing the 21-year-old at the beach, with his arm around her waist.

She wore a striped bikini and had headphones in her ears, while he wore thigh-grazing swim trunks and no shirt.

He helped the aspiring model snap some bikini pictures on the beach before moving to the water and snapping images of her there.

Aoki shared a number of bikini snaps on Friday morning while wearing a different swim suit, presumably taken by Vittorio.

Aoki and Vittorio, who is a father of two, share a 44 year age difference

Aoki is a model and a graduate of Harvard University; she got her degree at age 20 (in 2023), having been accepted into the prestigious school at age 16; seen in 2023

Aoki seen in St. Barts in social media pictures she shared last week

The pictures were presumably taken by Vittorio last week

He founded his restaurant group in 1995, seven years before Aoki's birth

Vittorio shares two children with ex-wife Swedish model Charlotte Bonstrom, 53: son Vittorio, 21, and daughter Valentina, 17; his children Vittorio and Valentina pictured

Vittorio Sr with his son Vittorio, 21

In June 2023, Aoki's mom Kimora Lee Simmons accused ex husband Russell Simmons (Aoki's father), 66, of 'bullying and threatening' Aoki and her sister Ming Lee Simmons, 24.

Kimora, 48, accused the Def Jam co-founder of 'threatening [their] kids' lives' and alleged that it led to Aoki having 'severe panic attacks' and 'placed on emergency medication' when she speaks to him.

Aoki shared text messages and a muted Facetime call to her Instagram, detailing his behavior toward her.

The young Harvard graduate was seen crying and looking visibly upset while on the call with her dad Russell, as he appears to angrily speak to her.

The family drama came weeks after Aoki graduated from Harvard with a double major, with mom Kimora revealing she is one of the youngest in recent history to do so. She was accepted at age 16.

In June 2023, Aoki's mom Kimora Lee Simmons accused ex husband Russell Simmons (Aoki's father), 66, of 'bullying and threatening' Aoki and her sister Ming Lee Simmons, 24; seen in 2001

Kimora, 48, accused the Def Jam co-founder of 'threatening [their] kids' lives' and alleged that it led to Aoki having 'severe panic attacks' and 'placed on emergency medication' when she speaks to him; seen in 2011

Aoki was seen crying and looking visibly upset while on the call with her dad Russell, as he appears to angrily speak to her

She also shared a messages where she told him how he allegedly treated her

Kimora spoke out as well and shared her support for her daughters

Kimora and Russell married in December 1998 in New York City after dating for four years; seen in 2003

Kimora and Russell married in December 1998 in New York City after dating for four years.

They met while Kimora modeled during Fashion Week in New York City, and went on to welcome two children together: Ming in 2000 (now 23) and Aoki in 2002.

In 2006, they announced they split, however they noted that they were separated already 'for some time.'

Russell told People magazine in a statement at the time: 'Kimora and I will remain committed parents and caring friends with great love and admiration for each other.'

Kimora filed for divorce in March 2008, citing irreconcilable differences - two years after their split.

She requested full legal and physical custody of their children, requesting he gets 'reasonable child visitation to be accompanied at all times by the children's nanny and security personnel.'

In January 2009, their divorce was finalized, according to Today Show.

In February 2009, it was reported that Russell has agreed to pay $40,000 a month in child support until their youngest reaches the age of 19.5 years old.

Kimora was granted sole custody of their girls.

She is also mom to kids Kenzo, 14, with ex Djimon Hounsou and Wolfe, eight, with ex Tim Leissner.

She adopted son Gary in 2020 when he was 10.

During the June 2023 exchange, Kimora said about Russell on her social media: 'I'm so sorry to have to do this. But this man has been threatening my kids' lives. I'm hearing so much more now. We won't be bullied, threatened, or afraid. Who gaf?!

Adding: 'No one should live like this. No one's child. This is abuse. Not okay. The threats, not okay. The fear mongering. Not okay' along side text messages shared by Aoki.

It appeared to have begun after the girls wished mom Kimora a Happy Father's Day instead of their father.

He shared an Instagram post that seemed to be a thinly veiled jab at Kimora; it was a quote that read: 'Stop telling fathers they should have fought harder to see their children and start asking mothers why he had to fight at all.'

Soon after, Aoki released the messaged and the muted Facetime call on her stories, also revealing she was done trying with her father.

'My father is not well, for years, he needs help and won't accept that he refuses to acknowledge he is not himself. He has threatened and bullied my sister, my grandma, he has harassed my grandma in the middle of the night in poor health, [sent] a man to my sister's apartment to scare her.'

'He lashes out at anyone who does not say "Ooh Russell everything is fine" well it's not fine,' she wrote.

One day later, Russell apologized for his behavior via his Instagram page, writing: 'DEEPLY sorry for being frustrated and yelling... but know this... there are no conditions... for sure I love you guys more than I love myself.'

Three months later, Kimora was asked if the situation improved between him and their daughters, to which she said 'no, I wouldn't say that,' adding: 'Just don't abuse my kids. Don't be ignorant to them or disrespectful. It wasn't a one-off thing. I'm not going to allow that. I'm not going to back down. My baby was worries, and she was crying, "I'm never going to work again" because he said crazy stuff." I just don't deal with him, and I don't have time for negativity,' via The New York Post. 

They welcomed two children together: Ming in 2000 (now 23) and Aoki in 2002; seen in 2006

Kimora with Ming and Aoki posing in her brand Baby Phat

Kimora seen walking down the Baby Phat runway in 2009 with Ming and Aoki

Vittorio founded Serafina Restaurant Group in 1995 with Fabio Granato in New York City. 

They have since expanded, with restaurants all over the world.

Vittorio was married to ex-model Charlotte for 20 years until she left him in 2021 - to marry her twin sister Cecilia's ex-husband Thierry Gillier - the founder of the fashion label Zadig & Voltaire. 

Vittorio and Charlotte have two children together: son Vittorio, who turns 22 in May, and daughter Valentina, who turns 18 in August. 

Cecilia served as the artistic director of Zadig & Voltaire since 2006 - however her social media now says she is the 'former creative director of Zadig & Voltaire.' It is unclear when she left her position.

Vittorio founded Serafina Restaurant Group in 1995 with Fabio Granato in New York City; the friends and business partners pictured in 2023

Vittorio was married to ex-model Charlotte for 20 years until she left him in 2021 - to marry her twin sister Cecilia's ex-husband Thierry Gillier - the founder of the fashion label Zadig & Voltaire; seen together

Vittorio and Charlotte pictured in 2010

The exes appear amicable - as they pose together with their son Vittorio on Mother's Day last year

Charlotte shared a snap of her son Vittorio, whom she shares with Vittorio Sr, last year on his 21st birthday in May 2023

Charlotte wished her and Vittorio Sr's daughter Valentina a happy birthday in August 2023 for her 17th birthday

In 2021, Vittorio told Page Six that he and Charlotte were getting a divorce because she wanted to get remarried.

He said: 'Charlotte and I are in the process of getting divorced – she wants to get remarried,' he said Wednesday.

'[She] is getting married to Thierry Gillier, the ex-husband of her sister.'

There was a brief rumor that they were switching spouses - and that he was involved with Cecilia, which he denied at the time.

'It is very difficult but I have nothing to do with the sister of Charlotte,' he insisted.

It is not clear when exactly Thierry and Charlotte allegedly started cheating on their respective partners though it is said to have been sometime during the pandemic.

The source told Page Six Charlotte had started 'secretly dating other people' because she was 'hurt' that Assaf 'spent time with models during their marriage.'

Cecilia is then thought to have learned about the double betrayal by her sister and her husband March 2020 with the source saying 'it broke Celia's heart'.

She posted cryptic posts on Instagram at that time, taking swipes at Gillier and Charlotte for lacking 'integrity.'

In one, posted March 13, 2021, she shared a meme reading: 'You're looking for three things generally, in a person: Intelligence, energy and integrity. And if they don't have the last one, don't even bother with the first two.'

She tagged her husband and sister in the post along with the hashtags '#thanks' and '#warrenbuffet'.