Vittorio Assaf Is ‘Having Fun’ With Aoki Lee Simmons Amid Their Romance

Vittorio Assaf is “having fun” amid his romance with Aoki Lee Simmons, a source tells Us Weekly exclusively.

“He has kids that are a little older than Aoki and it’s strange and out of character for him to be dating someone that young,” says the source, adding that Assaf, 65, “enjoys” having Simmons’ “company.”

Assaf and Simmons, 21, were spotted packing on the PDA during a beach vacation in St. Barts earlier this month. During their getaway, Assaf snapped pics of Simmons as she posed in the sand before they headed into the ocean for a dip.

“He is a free spirit and knows he can do whatever he wants at this stage in his life,” the insider says.

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Prior to his romance with Simmons, the Serafina Restaurant Group cofounder was married for 20 years to Charlotte Bonstrom. News broke in 2021 that the pair, who share kids Vittorio Jr. and Valentina, had split — and Charlotte was set to marry her twin Cecilia Bonstrom’s ex-husband, Thierry Gillier.

“Vittorio did have somewhat of a mid-life crisis after his very public divorce,” the insider says. “It was embarrassing for him that his wife left him, and he was heartbroken.”

When Charlotte moved on with Gillier, Assaf was rumored to have been linked to Cecilia — but he denied the claim. “It is very difficult,” he told Page Six in June 2021. “But I have nothing to do with the sister of Charlotte.”

Assaf is “a huge family man” and “very family focused,” the source says, adding that he’s “a really fun guy to be around” who “definitely commands a room.”

“He is very charming and women would often flock to him when he would visit his restaurants,” the insider notes.

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A separate source noted that Assaf is a “great guy and a great catch,” adding “age is just a number.”

After Assaf’s romance with Aoki became public, the twosome faced criticism for their 44-year age gap. However, her father, Russell Simmons, made it clear he’s supportive of his daughter.

“I’m not gonna kick and scream about her choices,” Russell, 66, told TMZ on Monday, April 8. “All I can do is offer my advice and unconditional love.”

Amid the chatter, Russell also penned a sweet message for Aoki. “Throw back from last fathers day nyc,” he captioned the post via Instagram on Saturday, April 6. “Bode bikram yoga express class .. vegan lunch cryotherapy vitamin drip … all around amazing day @aokileesimmons love you always.”