You’ve probably seen the photos. It’s the late 80s or maybe the peak of the 90s, and there’s Robert De Niro—the man who basically redefined grit in Hollywood—standing next to a woman who looks like she just walked off a high-fashion runway in Paris. That’s Toukie Smith.
Most people know her as the sister of the legendary designer Willi Smith or as Eva Rawley from the sitcom 227. But for nearly a decade, she was the woman standing beside one of the most private actors in history.
Honestly, their relationship was a bit of a mystery while it was happening. This wasn't a "red carpet every night" kind of vibe. It was something much deeper, much more complicated, and, in many ways, ahead of its time.
The Partnership Nobody Saw Coming
Robert De Niro had just wrapped up his first marriage to Diahnne Abbott when he met Toukie in 1988. Now, if you’re expecting a story about a whirlwind Vegas wedding, you’re looking at the wrong couple. They never actually got married.
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They just... were.
Toukie wasn't just "the girlfriend." She was a powerhouse in her own right. By the time they started dating, she had already been Bloomingdale's Model of the Year and had worked with basically every major house from Versace to Chanel. She had this energy that was impossible to ignore. De Niro, famously tight-lipped, seemed to find a match in her.
They lasted about eight years. That’s a lifetime in Hollywood years.
The Truth About the Breakup
It’s funny how people assume every celebrity split is a disaster. With Toukie and Robert, it was less of a "blow-up" and more of a "growing apart" situation that happened right as they were becoming parents.
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In October 1995, they welcomed their twins, Julian Henry and Aaron Kendrick (now Airyn), via a surrogate. This was 1995. Surrogacy wasn't the "standard" celebrity move it is today. It was a massive deal.
But by the time the twins were born, or very shortly after, the romantic part of their relationship was basically over. His publicist actually released a statement confirming the split just weeks after the babies arrived.
Imagine that. You’ve just had twins, and the world finds out you’re not together anymore.
They didn't hide in the shadows, though. They ended up in family court for a bit—not because they hated each other, but because they had to figure out how to navigate this new world of co-parenting twins who were biologically theirs but born via a third party. They eventually landed on a schedule where they’d swap the kids every four days. It sounds exhausting, but they made it work.
Breaking the Silence in 2025 and 2026
For years, the kids stayed out of the spotlight. Julian eventually caught the acting bug, appearing in things like In Dubious Battle and the show The First Lady. He’s got that De Niro look, no question about it.
But the real headlines started popping up more recently.
In April 2025, Airyn De Niro came out as transgender. In a world where celebrity families often stay quiet to protect "the brand," the response from both Toukie and Robert was remarkably human.
Robert De Niro, now 82, didn't give a scripted, corporate response. He basically told reporters that he loved and supported Airyn as his son, and he loves and supports her now as his daughter. He literally said, "I don't know what the big deal is."
It was a classic "Bobby" moment. Direct. No fluff.
Airyn’s interview with Them magazine was pretty raw, too. She talked about the anxiety of transitioning in such a famous family and the pressure of body standards. Toukie, ever the protective mother, has remained her daughter's biggest advocate, proving that while the "couple" ended in 1996, the family stayed intact.
Why Their Story Still Matters
If you look at the timeline, Toukie Smith and Robert De Niro were pioneers of the "modern family" before it was a buzzword.
- They weren't married.
- They used IVF and surrogacy when it was still a taboo subject.
- They co-parented across two different homes for decades.
- They’ve navigated their children’s evolving identities with a level of grace that many "traditional" families struggle to find.
Toukie once told the Los Angeles Times, "What's great about a private life is it's private." She wasn't kidding. Even now, you won't find her on a reality show spilling tea about her ex. There’s a level of mutual respect there that you just don't see often.
Actionable Insights for Following Celebrity Legacies
If you’re looking to keep up with how these families evolve, don’t just look at the tabloids. Look at the work.
- Watch Julian De Niro’s performances: He isn't just a "nepo baby"; he’s actually putting in the work in indie films and prestige TV.
- Follow the advocacy: Airyn De Niro’s journey is becoming a touchstone for transgender visibility in high-profile families.
- Respect the privacy: Toukie Smith’s choice to remain largely out of the press since the late 90s is a lesson in how to maintain dignity after a major public relationship.
The story of Toukie and Robert isn't a tragedy of a failed relationship. It’s actually a pretty successful story of two people who realized they were better as co-parents than partners and managed to raise children who are now finding their own voices in 2026.