When photos hit the internet of Harvard grad Aoki Lee Simmons kissing a man three times her age on a beach in St. Barths, the collective gasp was audible. It wasn't just a gossip story. It felt like a cultural flashpoint. Everyone had an opinion, and most of them weren't exactly kind.
The internet has a way of turning people into caricatures. But if you're looking for the current Aoki Lee Simmons boyfriend, the reality is actually a lot quieter than the tabloids would have you believe. In fact, the most "famous" relationship she’s had lately was over almost as soon as it started.
The St. Barths Fling That Set the Internet on Fire
Let’s be real. The 2024 "romance" with Vittorio Assaf was a whirlwind. It was weird, it was public, and it was deeply polarizing.
Assaf, the 65-year-old co-founder of the Serafina Restaurant Group, was spotted locking lips with a then-21-year-old Aoki. The age gap? A massive 44 years. Naturally, the commentary was brutal. Some called it "predatory," while others dug up old clips of Aoki joking to her dad, Russell Simmons, about getting a "sugar daddy" if he didn't raise her allowance.
But here is the thing: it wasn't a long-term love story.
Sources close to the family eventually told People that the whole thing was "never really a thing." It lasted about a week in the public eye. One minute they’re on IG Live together in the Caribbean, and the next, she’s back in New York, and he’s a footnote in her Wikipedia entry.
Kimora Lee Simmons and the "Predatory" Label
You can’t talk about Aoki’s dating life without talking about her mother, Kimora Lee Simmons. Kimora hasn't exactly been subtle about her feelings.
On a December 2025 episode of the Not Skinny But Not Fat podcast, Kimora got incredibly candid. She didn't hold back. She described the situation with Assaf as "predatorial and kinda crazy."
"I found out when the world found out. So that was what was so shocking." — Kimora Lee Simmons
Kimora's perspective is layered. She was 17 when she met Russell Simmons, who was 35 at the time. She’s lived the age-gap life. She knows the power dynamics involved. When she saw her daughter—a brilliant, Harvard-educated woman—navigating that same path, she was concerned. But she also chose to stay out of it. She wanted Aoki to make her own mistakes.
Honestly, that’s a tough spot for any parent. You want to protect them, but you also know that if you push too hard, you might just push them closer to the person you're worried about.
Who Is Aoki Lee Simmons Dating Now?
Since the Assaf drama fizzled out, the search for a new Aoki Lee Simmons boyfriend has mostly turned up empty. She’s been incredibly low-key.
Aoki seems to be focusing on her modeling career and her life as a young professional. She’s walked for major brands like Tommy Hilfiger and Michael Kors. She’s busy. She’s living that Gen Z life where every move is scrutinized, so she’s likely learned to keep the private stuff private.
There was a time back in early 2023 when she posted a Valentine’s Day photo with a young man, but that disappeared from the grid pretty quickly. Since then? Total radio silence on the relationship front.
Why the Public is So Obsessed
Why do we care so much? It’s probably the combination of her pedigree and her intellect.
- She’s a Simmons. That name carries weight in fashion and music.
- She’s a "Brainy Beauty." Graduating from Harvard at 20 is no small feat.
- The contrast between her academic success and the "sugar baby" optics of the Assaf fling was too much for the internet to ignore.
People wanted her to be "above" that kind of tabloid fodder. But at the end of the day, she was a 21-year-old exploring the world. Sometimes that involves making choices that look questionable on a smartphone screen.
💡 You might also like: Montero Lamar Hill: What Most People Get Wrong About Lil Nas X Real Name
Moving Past the Headlines
The Assaf chapter is closed. Kimora has spoken her piece. Russell Simmons has offered his "unconditional love" from afar.
If you're looking for deep insights into her current partner, you won't find one because she appears to be single—or at least very good at hiding a boyfriend. And honestly? Good for her. Navigating your early 20s is hard enough without a million strangers analyzing your "daddy issues" or your bank account.
The real takeaway here isn't about who she's dating. It's about how she's handling the transition from "child of celebrities" to "adult in the spotlight." She's learning that the public sphere is a minefield.
For those following her journey, the best move is to watch her career. The modeling gigs are getting bigger, and her voice on social media is becoming more refined. She's more than just a headline about an older man. She's a woman building a brand that's entirely her own.
To stay truly updated on her life, the best path is following her official social channels rather than the tabloid cycle. Most of what you'll see there is high fashion, travel, and the occasional family post. It's a lot less scandalous than the 2024 headlines, but it's a lot more representative of who she actually is. Focus on her professional milestones, as those are the things she’s actually choosing to share with the world right now.
Next Steps for Readers
- Check her Portfolio: Look at her recent work with Tommy Hilfiger to see her growth as a model.
- Listen to the Podcast: Find the December 2025 episode of Not Skinny But Not Fat for Kimora’s full perspective on celebrity parenting.
- Follow her Literacy Advocacy: Aoki often posts about her favorite books; it’s a great way to see the Harvard side of her personality.