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Boo’ed Up To The MAX! See The Photos Of Aoki Lee Simmons And Vittorio Assaf On Their Baecation

“Well, well, well! Aoki Lee Simmons and her 65-year-old boo thang Vittorio Assaf. As we last reported, the 21-year-old recently went viral for her steamy kiss with the restaurateur while on vacation.

Aoki Lee and Vittorio jetted off to St. Barts together, and photos surfaced of them enjoying a beach day. But lip-locking multiple times wasn’t the only thing these two did. Despite their 44-year age gap, they seemingly had a TIME both out and in the water.

Aoki Lee Simmons looked snatched in a tribal-print bandeau bikini. Meanwhile, her Italian bae went shirtless but wore light blue swim shorts and a chunky silver necklace.

Keep scrolling to see how they popped out together.

Photo credit: Spread Pictures/MEGA

Aoki Lee & Vittorio Getting Their Flirt On

As mentioned, the unofficially confirmed pair spent time frolicking in and out of the water. While chilling in the sand, they exchanged smiles and kisses amid conversation.

 

Spread Pictures/MEGA

 

Spread Pictures/MEGA

 

Photo credit: Spread Pictures/MEGA

 

Spread Pictures/MEGA

PDA aside, Vittorio was also putting in that overtime to snap photos of his lil’ model boo. And sis was working that camera and her angles!

PhotoSpread Pictures/MEGA

 

Photo credit: Spread Pictures/MEGA

 

Photo credit: Spread Pictures/MEGA

 

Spread Pictures/MEGA

 

Spread Pictures/MEGA

Aoki Lee and Vittorio also dipped into the crystal blue waters together!

 

 


Russell Simmons, Kimora Lee & A Resurfaced Video Enter The Chat

So, who is Vittorio Assaf? As mentioned, he’s a restaurateur, specifically the co-founder of New York City’s Serafina chain restaurants. According to Spread Pictures and MEGA, who obtained the baecation photos, Vittorio reportedly has a pattern of dating younger women.

In 2021, Assaf announced his divorce from his wife of over 20 years, Charlotte Bonstrom. Their split was a lil’ bit messy as he claimed his ex-wife left him after having an affair with her twin sister’s ex-husband. They share two children. He reportedly began dating 23-year-old model Nya Gatbel aftr the divorce, per Page Six.

Amid all the talk of Aiko’s dating life, her parents, Russell Simmons and Kimora Lee, seemingly broke their silence on the matter.

Russell shared a throwback photo, a rundown of the last time they hung out, and a reminder that he loves her. He also said he was waiting for her phone call. Meanwhile, her mother, Kimora took a humorous tone with the whole situation.

RELATED:Chile! Russell Simmons & Kimora Lee Seemingly React To Aoki Lee’s Viral Kiss With 65-Year-Old

As social media chats about Aoki’s life, they’re also digging up her old comments, particularly her telling Russell in 2022 that she will find “a sugar daddy” if he doesn’t give her money.

Watch the throwback clip below.

Cassandra Santiago

Cassandra Santiago is a multimedia journalist, editor, and editorial strategist with over a decade of experience shaping conversations across arts, entertainment, culture, and global news. A graduate of the University of Iowa, she has built a cross-platform career spanning newspapers, magazines, radio, and digital media. She joined The Shade Room five years ago and currently serves as a Senior Editor, where she leads editorial direction, oversees exclusive coverage, and trains and edits a team of writers. Cassandra has played a key role in developing high-impact content and editorial strategies for an audience of more than 30 million, contributing to platform growth, engagement, and monetization across multiple channels. In addition to her leadership role, she remains a daily contributor, with her articles generating more than 41 million views since 2023. Beyond The Shade Room, Cassandra offers freelance social media strategy services, speaks on the influence and impact of Black media at public panels, and owns Did It For You, an event design company in the DC, Maryland, and Virginia area. She is Poynter Institute–certified and was named to the DMV’s 35 Under 35 list in 2024.

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