How Old Was Russell Simmons When He Started Dating Kimora

So, you want to know the steamy, slightly eyebrow-raising math problem that is Russell Simmons and Kimora Lee Simmons? You’ve come to the right place. Grab your iced latte and prepare for a timeline that sounds like it was written by a mischievous genie. We’re diving into the question: just how old was the Def Jam mogul when he started dating his future supermodel wife?

The short, punchy, and deeply confusing answer is that Russell Simmons was 36 years old when he first started dating Kimora. And Kimora? She was just 17. Yes, you read that right. He was literally old enough to have bought her a legal beer (in 1992), but she couldn’t buy one for herself. It’s a gap that makes your high school math teacher weep and your tabloid editor grin.

Let’s set the scene, shall we? The year is 1991. Russell is a hip-hop god, a billionaire brand-builder who just watched his protégés, Run-D.M.C., conquer the world. He’s wearing all the cross pendants, chilling next to L.L. Cool J. Meanwhile, Kimora is a 5’11” high school junior in St. Louis who has already been scouted by Karl Lagerfeld for Chanel. She’s practically a unicorn: a teenage runway queen.

They met at a fashion show, and Russell later claimed he was “moved by her spirit.” Sure, Russell. I’m sure the “spirit” didn’t include her being the new face of Chanel while still having a curfew. The age gap is massive—a full 18 years. That’s not a generation gap; that’s a generation’s entire college career plus a mid-life crisis.

To put it in perspective: when Russell was a freshman at City College of New York in the early 1970s, Kimora wasn’t even a twinkle in her parents’ eyes. He was listening to Grandmaster Flash; she was listening to… well, her parents’ stereo. The math is brutal but funny: his first major label hit, “It’s Like That,” came out in 1983. Kimora was born in 1975. She was eight years old when his career boomed.

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But wait—it gets richer. They didn’t just date; they got married in 1998. By then, Russell was 41, and Kimora had just turned 23. That’s still an 18-year gap, but at least she could legally rent a car by then. The couple had two daughters, Ming and Aoki, whose names sound like characters from a sci-fi novel about fashion empires.

The funny thing? Everyone in the 90s treated this like it was totally normal. Tabloids called them “hip-hop’s power couple” without a wink. Today, if a 36-year-old started dating your 17-year-old neighbor, you’d probably call the cops and start a neighborhood watch. But the 90s were a different planet—weed was still illegal in most places, and age gaps were seen as “worldly” rather than “creepy.”

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Let’s not forget the surprising facts. Kimora didn’t even graduate high school until after they started dating—she skipped her prom to walk the Chanel runway. Russell, meanwhile, was a ten-time platinum producer. Imagine your dad’s boss taking you to prom. Awkward. Even more awkward: Russell’s first wife, a model named Althea, was also much younger. He had a type: very tall and very young.

But here’s the twist: Kimora turned out to be a savvy businesswoman who eventually ran Baby Phat into a $300 million empire. She wasn’t just a “teen bride”; she was a mastermind who learned the game early. She later said in interviews that she “matured fast” and that Russell was “a great mentor.” Mentor. Right. Like a life coach with a wedding ring.

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The relationship lasted 13 years before they divorced in 2009. Kimora was 34 by then—practically the same age Russell was when they started. She’s now married to a man her own age, a banker named Tīm Leissner (whoops, that ended badly too, but that’s another article). The point is: she grew up, and the age gap finally caught up.

So, how old was Russell Simmons when he started dating Kimora? The number is 36. But the real story is a wild ride through 90s culture, power dynamics, and the weird way we used to talk about love. It’s a cautionary tale wrapped in a mink coat and a pair of Baby Phat jeans. If you’re squirming, good—you should be. But also, we can’t help but laugh at the sheer audacity of it all.

In the end, Kimora got the last laugh. She built an empire, raised two daughters, and now runs a vegan lifestyle brand while Russell focuses on yoga and meditation—probably to atone for the sheer awkwardness of that first date. The moral of the story? Age is just a number, but in this case, that number is illegal in many states. Drink your coffee, thank your lucky stars you’re not a 90s supermodel, and never, ever ask a 36-year-old what they were doing with a 17-year-old. The answer is too funny—and too weird—to handle.