Everything We Know About Donald Trump's Relationship With Ex Kara Young

While much of the media focus has been on Donald Trump's marriage to Melania since 2005, his earlier relationship with Kara Young in the late 1990s was equally intriguing and far more cringe-worthy. Their love story began in 1997 at a party in the Hamptons. At the time, Young, a biracial model, was navigating a failing relationship with gossip columnist AJ Benza.

Enter Donald Trump, separated but married to Marla Maples, with whom he'd cheated on his first wife, Ivana Trump. Young, who was 28, was many years younger than 51-year-old Donald but fell for him because he was "funny" and had a "great personality." Mr. Trump was the final push the model needed to leave Benza.

The new couple quickly became a well-known item and received a ton of press when they stepped out together. They attended Kate Moss and Naomi Campbell's Halloween party in 1997 and Time Magazine's 75th anniversary in 1998 together. Unlike many of Donald's other relationships, this actually seemed to be going somewhere. Soon, Donald met Young's parents, and the relationship lasted around two to two and a half years — depending on who you ask, but they eventually called it quits.

Donald Trump and Kara Young mutually decided to end their relationship on good terms. In her words: "It just ran its course. There was never any enmity or 'I hate you.' There was none of that with us" (via Inside Edition). Towards the end of that same year, Donald began dating Melania Knauss, who was also a model and more than 20 years younger.

A few months into the relationship, Miss Knauss walked into Mar-a-Lago just as Young, who was supposed to be Donald's ex, was leaving. Ronald Kessler tells US Weekly that Melania almost left Donald over his model ex, as she broke up with him on the spot. However, Donald turned up the charm, and they made up soon after. Young also moved on, and their relationship seemed to be water under the bridge — until 2001.

It was a normal day on "The Howard Stern Show" on May 10. Stern had a couple of friends in the studio, including AJ Benza, Young's other ex. Donald was scheduled to call into the show the next day but informed Stern that there was a change of plans and that he would only be able to call in that very day. The real estate mogul called, and the first few minutes were understandably tense. Then, Donald began passive-aggressively attacking Benza for writing negatively about him in his new book. This spiraled into an argument about Kara Young.

AJ Benza accused Donald Trump of "going after" Kara Young, but the businessman gave a taunting reply: "I did more; I stole his girlfriend. But I didn't know I was stealing his girlfriend." Benza argued that Donald was being untruthful, revealing that he'd asked Donald to stay away from Kara. The on-air argument soon deteriorated into insults. "I had been very successful with your girlfriend. I can tell you that," Donald said, adding, "You know what bothered you a lot — it bothered you a lot, and it should bother you a lot." Benza replied, "She tells me you cut your own hair. Is that true?"

Donald Trump and A.J. Benza's interview went on for so long that Kara Young eventually got wind of it and called in. The model stated that she was displeased that they were still fighting over the issue. "They shouldn't fight with each other because it's something that's old ... They both have very big egos."

However, a guest caller phoned in asking Young about one of the many jabs Benza had thrown at Donald. "Kara, A.J. was saying that Donald was calling you incessantly trying to get you back. True or not?" Young initially denied it, but when pressed further, stated that she didn't "want to say anything to hurt any relationship [Donald] may be in at this time. So, I'll just, you know, drop it." 

Eventually, Kara Young explained that she wasn't initially committed to A.J. Benza or Donald Trump and asked them to bury the hatchet. "You guys be nice. Can you get along?" Eventually, the argument was squashed, and Donald ended up marrying Melania Knauss in 2005. Young married for the second time that same year to billionaire Peter Georgiopoulos. 

Despite the messiness of Kara Young and Donald Trump's interview on "The Howard Stern Show," the model has only given two interviews about her ex — one to The New York Times in August 2017 and another to Inside Edition in 2022. In 2017, she told The New York Times that she had never witnessed Donald being racist but added that he often believed racial stereotypes. "We went to the U.S. Open once, and a lot of black people came because it was Venus and Serena. He was impressed that a lot of black people came to the U.S. Open because they were playing."

In 2022, Young spoke again when an anecdote in Maggie Haberman's book "Confidence Man" went viral. Young confirmed to Inside Edition that Donald had once joked that she got her intelligence from her white father and her looks from her black mother. When Young told him that his statement wasn't funny, he'd brushed it off, saying that it was a joke and he hadn't meant it. She also added that she didn't think Donald should run for president in 2024 but suspected he would.