Fans concerned over ‘creepy’ video of Aoki Lee Simmons, 21, and ‘boyfriend’ Vittorio Assaf, 65, in St. Barts

Aoki Lee Simmons’ bizarre behavior while filming a new Instagram Live video has fans concerned.

The model, 21, went live on the app after she was seen locking lips with 65-year-old restaurateur Vittorio Assaf, whom she referred to as her “boyfriend” in the video.

“Last day in St. Barts. I’m so sad but I’m very happy,” Simmons told her followers, as seen in screen-recordings shared by several fan accounts. “When I return home, everyone who knows me will be getting a happier, more chilled out version of me.”

The 21-year-old was seen kissing restaurateur Vittorio Assaf. Aoki Lee Simmons/Instagram The Serafina mogul is over four decades older than the model. Aoki Lee Simmons/Instagram

The youngest daughter of Russell and Kimora Lee Simmons seemed to slur her words before repeatedly asking Assaf to buy her a crepe.

“Would you like to share your favorite thing about the trip?” she asked the Serafina co-founder, who did not appear on camera but could be heard in the background.

“You … [being] with you,” he said, to which she giddily quipped, “He said me.”

The model went live on Instagram during the final day of her tropical vacation this week. Aoki Lee Simmons/Instagram The youngest daughter of Russell Simmons filmed the video in the back of a moving car. WireImage

Elsewhere in the clip, Aoki was heard asking her beau questions before repeatedly shushing him.

“Baby, do you want to go to Kenya?” she asked, then told him, “Shut up, never mind.” 

The Harvard University graduate, who filmed the video in the back of a car, went on to reveal some of her favorite designer brands as she and her new man drove past several stores.

She was bizarrely asking her new beau questions before telling him to “shut up.” FilmMagic The model added, “You know what I also like a lot: Cartier.” Rupert Ramsay/BFA.com/Shutterstock

“I am a big Bvlgari person,” she said, mispronouncing the brand’s name. “I just want to make that very clear. You know what I also like a lot: Cartier.”

---

For more Page Six you love…

Listen to our weekly “We Hear” podcast Shop our exclusive merch

---

Fans were quick to express concern over Aoki’s IG Live video – and the nature of her new relationship – after seeing pics of the model packing on the PDA with Assaf earlier this week.

She also begged Assaf to buy her a crepe. Patrick McMullan via Getty Images “This video is weird and gives me the creep,” one person commented on the clip. Rick Davis / SplashNews.com

“Shes actually giving little girl energy and it’s making it extremely creepy,” one person wrote.

“This is disturbing. She’s not just young but young minded,” another added, while a third chimed in, “Everything about this video is weird and gives me the creep.”

Others were puzzled by Aoki’s peculiar behavior, which seemed at odds with her Ivy League education.

“I was expecting a different *tone* of conversation from a Harvard scholar,” one person commented, while another added, “Getting into Harvard & doin this jus don’t make a lick of sense.”

Her parents have shared cryptic social media posts in recent days, though neither has addressed the situation directly. WireImage Aoki graduated from the prestigious Harvard University in 2023. FilmMagic

Aoki made headlines after Page Six exclusively published photos of her making out with Assaf, who is more than four decades her senior.

Both Russell, 66, and Kimora Lee, 48, have shared cryptic social media posts in the wake of Aoki’s hot and heavy romance with the Italian businessman, though the up-and-coming model hasn’t addressed the relationship herself. Her parents – who have an 18-year age gap themselves – were married from 1998 to 2009 and also share 24-year-old daughter Ming Lee Simmons.

While Aoki has mostly kept her dating life out of the public eye, Assaf made headlines when his ex-wife, Charlotte Bonstrom, left him for her twin sister’s ex-husband, Thierry Gillier.