Trump Family Exes Have Had Plenty To Say About Their Former Beaus

The Trumps aren't exactly known for their relational diplomacy. As Donald's ex-wife Marla Maples told The Daily Beast in 2016, he "shoots from the hip and he says whatever flies out at the time," which isn't always a great strategy when it comes to marriage, nevermind global politics. If anything, it's surprising that so many members of the Trump family do appear to have reasonably stable relationships. Donald's son, Eric, seems to have been a monk before he met his now-wife Lara in 2008; his daughter, Tiffany, is likewise scandal-lessly married to businessman Michael Boulos; and the most interesting chapter of daughter Ivanka's love life is her ex-boyfriend's arrest for cocaine possession alongside the bassist of Maroon 5.

When it comes to Donald himself and the son named after him, however, things aren't such smooth sailing. The president's marriages and divorces are the stuff of tabloid legend, and Don Jr.'s divorce and subsequent engagements (yes, plural) aren't far behind. So, how do their exes feel about all this? They've had plenty to say, from the most damning accusations to the warmest of regards.

Donald Trump's first wife, Ivana, was hands down the most vocal about her unhappiness in her marriage, which lasted from 1977 to 1990. In court filings related to their divorce, she accused him of relentless verbal abuse and even described one incident of vicious physical and sexual violence. Their divorce was granted on the grounds of cruel and inhumane treatment of her by Trump, though his lawyer said this referred to cruelty inflicted by the media in the wake of their discovery of Trump's affair with Marla Maples in 1990. Ivana later insisted that she hadn't meant to accuse him of any crimes.

In her 2017 memoir, "Raising Trump," she looked back much more fondly on her marriage, and she reported throughout Trump's political career that she remained one of his closest friends and advisers. She did write that Trump wasn't a very involved father, but she attributed that to an ineptitude with children rather than indifference, as well as her own desire to singlehandedly shape her offspring. As a result, she admitted, he didn't really connect with their sons Eric and Donald Jr., or their daughter, Ivanka, until they were adults.

Though Donald Trump was reluctant to marry again, he proposed to Marla Maples after the 1993 Long Island Rail Road shooting made him realize life is short, she told The New York Daily News. They married that year, just after Maples gave birth to Tiffany Trump — and divorced in 1999 when, Maples says, their conflicting perspectives on the world and raising children in it became insurmountable. Specifically, as a Southern Baptist more concerned with philanthropy and spirituality than lavish galas and material success, she felt out of place in Donald's life of luxury and longed to flee the New York spotlight for beachier pastures.

If that all sounds suspiciously diplomatic, most of what Maples has said about Donald concerns how little she can say about him. Aside from one reported 1999 vow (via The Daily Beast) to "tell the people what he is really like" if he ran for president, she's been tight-lipped about her ex's character, citing concerns about her and her daughter's safety, a desire to protect her daughter's relationship with her father, and a philosophical aversion to trash talk. She also may or may not be worried about him cutting off her alimony for violating their non-disclosure agreement, as he did in response to her previous threat to blab. All she'll say is that she's more liberal than he is on issues such as reproductive and LGBTQ+ rights.

Former Trump adviser and fundraiser Kimberley Guilfoyle had every reason to go scorched putting green on the family following the 2024 end of her engagement to Donald Trump Jr. From the start, their relationship exhibited major warning signs they were never meant to last. After a six-year relationship and four-year engagement, tabloids published photos of Don Jr. frolicking around Palm Beach with socialite Bettina Anderson in December 2024, and claimed the pair were spotted kissing. Don Jr. and Anderson were making no attempt to hide their relationship, even before his breakup with Guilfoyle was confirmed. At the same time, in a move reported as a possible attempt to exile Guilfoyle, Donald Trump nominated her as the U.S. ambassador to Greece.

According to Guilfoyle, however, she's living her best life. In a January 2025 interview with The New York Times, she reported that she was thrilled with the nomination and her work in Greece. There was no exile, she claimed; she was given the job because the president knew she had taken university classes in ancient history that sparked a passion for Greek culture. She denied any beef with the Trump family and even wished her ex all the best in his now-engagement to Anderson. "I'm happy for Don," she insisted. It's not like a government-sanctioned "Mamma Mia!" experience is that bad of a punishment anyway.

Remember when Donald Trump was better known as one of the most powerful men in the world, aka a game show host? In 2011, he was filming Season 5 of "The Celebrity Apprentice," which featured "Making the Band" singer Audrey O'Day. During that time, rumors swirled that O'Day had begun a relationship with Donald's married son, Donald Jr.

The affair reportedly ended after Don Jr.'s wife, Vanessa, found illicit messages Don Jr. and O'Day had sent each other, but neither acknowledged the relationship until O'Day referred to Don Jr. as her soulmate on a 2019 episode of MTV's "Ex on the Beach." She pleaded with him to appear on the show, which reunited exes, and called his then-girlfriend Guilfoyle "crazy-looking." When Don Jr. failed to respond, however, O'Day told People she no longer recognized the man she fell in love with. She opened up again in 2025, telling Us Weekly that Don Jr. had made her feel beautiful and smart in a way no other man ever had.

No word on how Donald Trump Jr.'s ex-wife, Vanessa, feels about Audrey O'Day's statements. Since Vanessa filed for divorce in 2018, her and Don Jr. have limited their public statements to enthusiastic Mother's and Father's Day wishes and social media likes. In an uncharacteristically outspoken moment, Vanessa did defend Don Jr.'s relationship with Guilfoyle, confirming that they'd been long separated by the time it began and lamenting the media's vitriol for any woman associated with him. In fact, she threw her support behind the couple before they had even made it official.

Maybe that's because she had long since moved on herself (not to mention totally transformed). In 2021, a book authored by Pulitzer Prize–winning reporter Carol Leonnig detailed Vanessa's alleged relationship with a Secret Service agent following her divorce. In 2025, Tiger Woods confirmed he was dating Vanessa, and while her ex-husband's feelings about the relationship aren't known, her ex-father-in-law is over the moon. In fact, Donald Trump might be a little too excited about the match, singing Woods' praises following the announcement. We're not saying Donald loves Woods more than his own son, but we are saying he's only given one of them the Presidential Medal of Freedom.