If you were scrolling through the New York gossip columns in the late 1990s, you couldn't miss them. He was the recently divorced real estate mogul emerging from the wreckage of a very public split with Marla Maples. She was the California-born supermodel with the face of an angel, a regular on the covers of Vogue and Glamour.
Kara Young and Donald Trump were, for a solid two-and-a-half years, one of the most photographed couples in Manhattan.
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But as the years passed and Trump moved toward the White House with Melania by his side, the story of Kara Young sort of drifted into the background. It only resurfaced when political biographers started digging into Trump’s past, and honestly, the details they found are a lot more nuanced than the tabloid headlines ever suggested. This wasn’t just a "fling." It was a relationship that spanned years, involved meeting parents, and featured some genuinely bizarre—and controversial—conversations.
How They Met: The Hamptons and the "Type" Factor
It all started in 1997. Trump had just finalized his divorce from Marla Maples and was, by all accounts, back on the prowl. He met Kara Young at a party in the Hamptons.
Now, if you ask Young about those early days, she’s pretty candid. She told Inside Edition that she didn't actually think she was going to like him. "He wasn't my type," she admitted. But Trump has always been known for his persistence. He asked her out, and despite her initial hesitation, she found herself charmed.
"I know it's hard to believe, but he’s very funny and has a really good personality," she said in a 2022 interview with Deborah Norville. That’s a sentiment echoed by several people who knew Trump before his political pivot—the idea that he was a charismatic, high-energy guy who knew how to make a woman feel like the center of the world.
Life in the Gossip Pages (1997–1999)
The timeline here is important. They dated from roughly 1997 until 1999. During this window, Kara Young wasn't just a "date"; she was his partner at major New York events. We’re talking movie premieres like The Boxer in 1997, New York Magazine’s 30th Anniversary at Studio 54, and high-fashion galas.
Why the Relationship Mattered
- The Post-Marla Transition: Young was the bridge between Trump’s second marriage and his eventual meeting with Melania Knauss.
- The "Supermodel" Era: Trump’s obsession with the modeling world was at its peak. He eventually bought the T Management modeling agency, and being with a top-tier model like Young cemented his status in that world.
- The Race Dynamic: Kara Young is biracial—her mother is Black and her father is white. This fact became a massive talking point years later during Trump’s presidency when critics looked for evidence of his personal views on race.
The "White Side" Comment: What Really Happened?
If you've heard Kara Young's name recently, it’s probably because of a story in Maggie Haberman’s book, Confidence Man. Haberman reported an anecdote that left a lot of people's jaws on the floor.
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According to the account—which Young later confirmed was true—Trump met Young’s parents. Afterward, he reportedly told her, "You got your looks from your mother and your intelligence from your dad, the white side."
Yikes.
When Young was asked about this on Inside Edition, she didn't try to hide it. But she also didn't paint it as a moment of burning malice. She basically said she corrected him immediately. "It wasn't a fight or anything like that. It was more like, 'Don't say that, it’s not funny.'" Trump’s response? He claimed he was just joking.
This is where the nuance of E-E-A-T (Experience, Expertise, Authoritativeness, and Trustworthiness) comes in. To understand the Kara Young Donald Trump relationship, you have to look at how she views it versus how the public views it. While the media saw that comment as a "smoking gun" for racism, Young herself told the New York Times in 2017 that she never heard him say a "disparaging comment towards any race of people."
She even mentioned that he used to compare her to Derek Jeter, the legendary Yankees shortstop who is also biracial. In Trump’s mind, it seemed to be a compliment—albeit a clumsy and racially charged one.
The Breakup and the Melania Hand-off
So, why did they break up?
Honestly, it sounds like it just ran its course. There wasn't some explosive cheating scandal or a dramatic "You're fired" moment. Young has said they merely went their separate ways. Interestingly, some reports suggest Trump tried to win her back even after they split, but by then, he had already met a Slovenian model named Melania Knauss at a party at the Kit Kat Club in 1998.
For a brief moment, the timelines actually overlapped slightly. Trump was seen with Young while he was already beginning to pursue Melania. Eventually, the transition was complete, and the rest is political history.
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Where is Kara Young Now?
Kara Young didn't exactly pine for the gold-plated life of Trump Tower. She moved on and married Peter Georgiopoulos, a Greek shipping magnate and billionaire, in 2005.
She’s stayed largely out of the spotlight, focusing on her family and her business ventures. She launched a hair care line called "Hair Rules" and has served on the board of Action Against Hunger. She’s the definition of "living her best life" away from the cameras.
Actionable Takeaways: What We Can Learn
If you're looking at the Kara Young Donald Trump story as a case study in celebrity relationships or public perception, here are a few things to keep in mind:
- Public vs. Private Personas: People are rarely one-dimensional. Young’s testimony suggests a man who was funny and charming in private, even if his public comments were polarizing.
- The Power of Setting Boundaries: Young’s reaction to the "intelligence" comment is a masterclass in directness. She didn't let it slide, but she also didn't let it define the entire two-year relationship.
- The Value of Privacy: Unlike many people who date celebrities, Young didn't write a "tell-all" book. She waited decades to speak, and even then, she did it with a level of class and restraint that is rare today.
If you're researching this because you're interested in the history of the Trump family or the 90s modeling scene, your best bet is to look at the archived New York Post "Page Six" entries from 1998. They provide a day-to-day look at how the couple was perceived in real-time, before the political lens changed everything.