Aoki Lee Simmons, 21, kisses Serafina co-founder Vittorio Assaf, 65, on romantic trip to St. Barts

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A 43-year age difference didn’t stop these two from having some fun in the sun.

Aoki Lee Simmons, 21, was spotted kissing restaurateur Vittorio Assaf, 65, during a romantic vacation to St. Barts on Tuesday.

In photos obtained by Page Six exclusively, the youngest daughter of Kimora Lee Simmons and Russell Simmons packed on the PDA with the much-older Serafina co-founder while enjoying time at a beach.

Page Six obtained photos of the model kissing the Serafina co-founder in St. Barts on Tuesday. Spread Pictures/MEGA At one point, Aoki posed for Assaf as he took pictures of her with his phone. Spread Pictures/MEGA She modeled different poses as he snapped away. Spread Pictures/MEGA

At one point, Aoki posed for Assaf as he took pictures of her with his phone. They also took a dip in the clear blue water and shared a steamy kiss while on the white sand.

The model wore an olive-green bikini with a tribal print on the front, while Assaf went shirtless, only sporting a pair of light-blue-and-white-printed swim trunks.

Page Six reached out to reps for both Aoki and Assaf for comment but did not immediately hear back.

They also took a dip in the clear blue water. Spread Pictures/MEGA Simmons wore an olive-green bikini. Spread Pictures/MEGA It had a tribal print on the front. Spread Pictures/MEGA

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On Friday, Aoki posted some snaps from her trip to the Caribbean island on Instagram — but she notably did not include her beau in any of them.

“Girls (possibly mermaids!) on film,” she captioned a carousel of pictures of herself posing in a bikini near a huge rock.

And on March 27, she shared a video of herself on a beach wearing the same bikini as she did in the photos we obtained of her and Assaf together.

The youngest daughter of Russell Simmons and Kimora Lee Simmons also had a wicker handbag that she brought to the beach with her. Spread Pictures/MEGA Assaf went shirtless for the outing. Spread Pictures/MEGA The dad of two wore a pair of light-blue-and-white-printed swim trunks. Spread Pictures/MEGA

The Milan-born businessman also posted pictures from his trip, featuring one of his friends whom he said he has known for “25 years.”

Assaf made headlines in 2021 when his now-ex-wife, former model Charlotte Bonstrom, left him after having an affair with her twin sister’s ex-husband, Thierry Gillier.

“Charlotte and I are in the process of getting divorced — she wants to get remarried,” Assaf told Page Six at the time. “[She] is getting married to Thierry Gillier, the ex-husband of her sister.”

On Friday, Aoki posted some snaps from her trip to the Caribbean island on Instagram. Spread Pictures/MEGA She did not include Assaf in any of them. Spread Pictures/MEGA On March 27, she shared a video of herself on the beach wearing the same bikini as the photos we obtained. Spread Pictures/MEGA

Assaf and Bonstrom were married for more than 20 years and share two kids: Vittorio Jr. and Valentina.

The restaurateur was most recently linked to 24-year-old model Nya Gatbel.


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Meanwhile, Aoki is typically private in her personal life.

Last February, however, she shared a picture with her then-boyfriend in honor of Valentine’s Day.

Assaf also posted pictures from his trip, featuring one of his friends whom he said he has known for “25 years.” Spread Pictures/MEGA The businessman made headlines in 2021 when his now ex-wife, former model Charlotte Bonstrom (far left), left him after having an affair with her twin sister’s ex-husband, Thierry Gillier. Patrick McMullan via Getty Images Aoki usually keeps her private life off social media. WireImage

Aoki clapped back at haters after the photo was met with backlash from fans who questioned why the Harvard grad — who is Japanese and African American — was dating outside her race.

“It’s genuinely so awful. How is any young person supposed to have a normal well adjusted life if this is what happens over a Godamn [sic] tagless valentines day post?!” she wrote on her Instagram Stories at the time.

“Sure I guess I knew the world was stuck in 1950 and would have some recessive & to say about something as simple as an interracial relationship……. Like that’s truly sad, especially from people of color, but it was expected.”

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