Affair Rumors That Have Plagued The Trump Family

In January 2011, Donald Trump appeared on "The Oprah Winfrey Show" alongside his third wife, Melania Trump, and his five children. At the time, Donald was exploring a run for the presidency; he wound up bowing out of the race that May, but the family interview on "Oprah" seems to have been meant to do some damage control on the real estate tycoon's reputation, turning the tabloid fixture into a respectable family man. "I've always said I've been a great father. Less of a good husband," Donald said, adding, "I love my family."

That would be a telling remark all its own, but Donald went into further detail. "We were helped by the fact that I never left anyone for Melania," he said. "When you leave for somebody, it's very hard to blend that family, but I never left [anyone] for Melania." (According to The List's timeline of Donald's relationship with Melania, that may not be true.)

He's referring, of course, to the fact that he is well-known for having had a wandering eye in the past. In fact, the former president isn't the only member of the Trump dynasty to have been dogged by stories of infidelity throughout the family's time in the public eye. Some have been proven, while others remain only rumors, but everyone from Melania herself to various Trump children have been accused of having had affairs. These are the affair rumors that have plagued the Trump family.

Long before Donald Trump entered politics, he was known as a fixture on the New York City social scene. His marriage to his first wife, Ivana Trump, was covered endlessly by the tabloids, who cared even more when it was clear that the marriage was on the outs. It was an open secret that Donald was engaging in an affair with Marla Maples, a relationship that would lead to the downfall of his marriage to Ivana.

According to sources who spoke with Vanity Fair, Donald's mother asked Ivana, "What kind of son have I created?" Donald Trump Jr., it seems, was distraught about his father stepping out on his mother. To control the narrative, Ivana hired a public relations team. "This is all very calculated. Ivana is very shrewd," a source told the magazine. It worked, and Donald told Vanity Fair that he understood why the public felt bad for Ivana. "When a man leaves a woman, especially when it was perceived that he has left for a piece of a** — a good one! — there are 50 percent of the population who will love the woman who was left," he complained.

In 2023, questioned amid charges that he assaulted E. Jean Carroll, Donald said he couldn't recall whether he'd had an affair with Maples. "It could be a lapover," he claimed (via The Washington Post), "but I don't really know."

Donald Trump met adult entertainer Stormy Daniels at a golf tournament, kicking off a relationship that would prove to be one of the most consequential in his lifetime. Days before the 2016 election, long-term fixer Michael Cohen paid Daniels $130,000 not to talk to the press. That illegal hush money payment would ultimately lead the former president to be convicted of 34 felonies, the first former president in American history to earn that distinction.

Daniels claimed that the first night they were together, Donald proudly showed her a magazine that had his photo on the cover. "I was like, 'Someone should take that magazine and spank you with it,'" Daniels recalled in an interview with CBS News. "And I'll never forget the look on his face." Daniels said she asked Donald about the fact that Melania Trump had just given birth a few months earlier, but he insisted that the relationship was over. "He brushed it aside, said, 'Oh yeah, yeah, you know, don't worry about that. We don't even — we have separate rooms and stuff.'"

Later, at the hush money trial, Daniels testified to her secrecy afterward. "I told very few people that we had sex because I felt very ashamed that I didn't stop it," she said. For his part, despite the felony conviction, Donald still denies anything happened. At a presidential debate in 2024, he insisted (via the BBC), "I didn't have sex with a porn star."

When Donald Trump was elected president, his wife Melania Trump didn't immediately move into the White House to be with him. Instead, eschewing the moves typically expected of a first lady, Melania continued to live in Trump Tower, in New York City, for the first year of the administration. It didn't take long before people online began to speculate about why that was, including novelist Monica Byrne. Byrne claimed on X, formerly Twitter, that Melania was in a relationship with Hank Siemers, head of security at the Tiffany's location in Trump Tower. "with DT's knowledge," she wrote (via Perez Hilton). "They had an agreement (written, I think) that if DT lost the election, they'd get divorced. But then he won."

Comedian Noel Casler, who worked on "The Celebrity Apprentice," chimed in to insist, "Melania didn't live with him in Trump Tower either, she lived with her boyfriend. We had to book the transpo on 'Apprentice' Finales and her pick-up was NOT on 5th Ave."

After recommending that journalists look into her allegations independently, Byrne even tagged the president to get his thoughts on the matter. "Hi @realDonaldTrump! We're all wondering if your wife @MelaniaTrump is having an affair with the head of security at Tiffanys or nah?" He did not, ultimately, chime in.

In 2018, shortly after Vanessa Trump filed for divorce from Donald Trump Jr., Page Six reported on an alleged affair between Donald Trump Jr. and former Danity Kane singer Aubrey O'Day. She was a contestant on "The Celebrity Apprentice" when Don Jr. was involved in the show, and they evidently struck up a relationship on set. "He told her that his marriage was already in the process of dissolving," a source told the outlet; it would be many years before Don Jr. and his wife actually divorced.

Since details about the alleged affair surfaced, O'Day has spoken out about the supposed dalliance multiple times. On former Trump fixer Michael Cohen's podcast "Mea Culpa," O'Day claimed Don Jr. was different back then. "You know what a bleeding-heart liberal I am. You know how I'm a social justice warrior since I was born. Raised by one," O'Day said to Cohen. "There's no way that I ever could have loved somebody [like] what we see today." She claimed he'd been comfortable enough in a gay club, for example, that they allegedly hooked up in the club bathroom. Nowadays, Don Jr. is an outspoken opponent of the LGBTQIA+ community.

It all fell apart when Don Jr. left his phone out while he took a shower, leading Vanessa to uncover what a source told People were "sexy texts." They added, "This is how Vanessa found out and the affair ended." 

Stormy Daniels isn't the only adult entertainer that Donald Trump allegedly had an affair with. He's also rumored to have had a relationship with Playboy Playmate Karen McDougal, according to an investigation by Ronan Farrow that was published in The New Yorker. In a handwritten account of the affair obtained by Farrow, McDougal detailed a relationship was said to have begun after Trump filmed an episode of "The Apprentice" at the Playboy Mansion in the 2000s. "We talked for a couple hours — then, it was 'ON'! We got naked + had sex. He offered me money. I looked at him (+ felt sad) + said, 'No thanks — I'm not 'that girl.' I slept w/you because I like you — NOT for money," she wrote. "He told me 'you are special.'"

The story was purchased days before the 2016 election by American Media Inc., a publishing company that manages tabloids like The National Enquirer. Details, however, were never published, which Farrow notes aligns with a strategy called "catch and kill." The story did eventually leak, though the White House denied the affair. "This is an old story that is just more fake news," they said.

McDougal regrets the deal. She told The New Yorker, "It took my rights away. At this point I feel I can't talk about anything without getting into trouble, because I don't know what I'm allowed to talk about. I'm afraid to even mention his name."

Nikki Haley and Donald Trump have had a contentious relationship. She was one of the only Republicans to challenge him for the 2024 Republican nomination, criticizing him on the campaign trail. According to The Guardian, she said, "We need a president that's going to give us eight years of focus and discipline, not one that's going to be sitting there ranting about how he's a victim." She did, however, appear at the Republican National Convention, endorsing the man she said was unfit for office. "My message ... is simple: You don't have to agree with Trump 100 percent of the time to vote for him," she said (via PBS).

The former South Carolina governor was, in fact, part of the Trump administration, his Ambassador to the United Nations. Her presence in the administration even sparked rumors that there was something more going on than just an employee/boss dynamic. 

Promoting "Fire and Fury" on "Real Time with Bill Maher," Michael Wolff suggested Trump was having an affair, though he declined to say with whom. "It was so incendiary that I just didn't have the ultimate proof," Wolff said. Readers of the book noticed a sentence about Trump spending an inordinate amount of time with Haley on Air Force One, leading her to deny the insinuation to Politico. "It is absolutely not true," she said. "It is highly offensive, and it's disgusting." It's not the only affair rumor that has followed Haley.

According to Pulitzer Prize-winning journalist Carol Leonnig's book "Zero Fail: The Rise and Fall of the Secret Service," multiple members of the Trump family may have had inappropriate relationships with Secret Service agents. That includes Vanessa Trump, ex-wife of Donald Trump Jr. "Secret Service agents reported that Vanessa Trump had started dating one of the agents who had been assigned to her family," Leonnig wrote.

The former president's youngest daughter Tiffany Trump, too, allegedly grew very close with a Secret Service agent following a breakup. "In the aftermath, she began spending an unusual amount of time alone with a Secret Service agent on her detail," Leonnig wrote. "Service leadership became concerned at how close Tiffany appeared to be getting to the tall, dark, and handsome agent." Ultimately, the agent was reassigned after concerns were raised. "This is nothing more than gossip and is simply not true," a spokesperson told The Washington Post. "Tiffany's experience with the Secret Service was entirely professional."

A Secret Service spokesperson didn't exactly deny the allegations when People contacted them for comment. "The U.S. Secret Service is aware of an upcoming book which re-hashes past challenges the agency overcame and evolved from," the spokesperson said. "Now and throughout its 156 year history, the agency's skilled workforce is dedicated to the successful execution of its critical protective and investigative missions." Well, okay then.