Famous Age-Gap Couple: Aoki Lee Simmons (21) and Serafina co-founder Vittorio Assaf (65)

Tamantha Ryan posted on "Page Six": "Aoki Lee Simmons, 21, kisses Serafina co-founder Vittorio Assaf, 65, on romantic trip to St. Barts" (April 5, 2024) Ryan wrote that 21-year-old Aoki didn't let her 43-year age-gap with 65-year-old Assaf stop her from having a "romantic vacation" on St. Barts with the grey headed restaurateur. 

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.

However, the pictures of the vacationing age-gap couple were obtained exclusively by Page Six, because neither Aoki or Assaf posted vacation pictures of them together on their respective social media accounts. Ryan wrote:

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.

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

However, Aoki, an apparently unabashed teleiophile, posted an Instagram Live video with Assaf (off-screen). In the video, Aoki referred to Assaf as her "boyfriend", and she said that she was "happier" and "more chilled out". And the age-gap couple referred to each as "baby".

Vittorio Assaf and Nya Gatbel (Getty Images)

In addition, Ryan shared that prior to Aoki, Assaf was "linked to 24-year-old model Nya Gatbel." However, Francesca Bacardi reported in the "Page Six" piece: "Serafina restaurateur Vittorio Assaf makes full recovery after week-long hospitalization" (June 28, 2023) that Nya was 22 when she was Assaf's girlfriend.

Russell Simmons and Kimora Lee (Getty Images)

Connectedly, per Barnaby Lane's Business Insider piece "A complete timeline of Russell Simmons and Kimora Lee Simmons' marriage and divorce", Aoki's parents, Russell Simmons and Kimora Lee Simmons, met when Russell was 35 and Kimora was 17. Lane wrote:

Simmons, the cofounder of Def Jam Records, first met Lee while she was modeling at New York Fashion Week in 1992, according to People.

Despite Simmons being 35, and Lee being just 17 and still a sophomore in high school when they met, they soon began dating.

In 2020, Simmons said that they didn't begin dating until Lee turned 18 and that Lee's mother approved of their relationship.

"She was legal at 17 but she turned 18 that may her mother and her manager Bethann Hardison approved supported and rushed us (we really didn't need a push)," he wrote on Instagram.

Per Lane, Russell and Kimora Lee were in their age-gap relationship for approximately 14 years.