The Scandalous Affair Rumors The Trump Family Just Can't Shake

For decades, Donald Trump has been plagued by an endless barrage of rumors and accusations on both the personal and professional fronts. When it comes to his private life in particular, the 45th president has faced a long list of affair rumors dating back to the 1980s. However, he's not the only Trump family member who's had to deal with alleged headline-making flings. Although they've all vehemently denied any impropriety, the stories have failed to go away. Rather, they've repeatedly resurfaced through the years, even if some are admittedly bizarre. In 2019, for example, then-First Lady Melania Trump greeted Canadian Prime Minister Justin Trudeau with a kiss at the G7 summit. It was an innocent act, but soon, folks were tweeting wild conspiracies about a Melania-Trudeau affair without any evidence. Some went as far as to share photos of the PM alongside snaps of Barron Trump, highlighting their purported resemblance. One such skeptic wrote on X, "Try to convince me that Barron is actually Donald's kid."

Despite such wackiness, other stories of infidelity have been much more convincing. Here are all of the biggest affair rumors the Trump family just can't shake.

Melania Trump has had to deal with never-ending infidelity headlines, but she's not Donald Trump's first wife to face such rumors. In 1977, Donald married Ivana Trump. Not only was she the mother of his first three children, she was also an integral part of the Trump Organization. However, their seemingly perfect union came crashing down in 1989 when Ivana learned of her husband's alleged years-long affair with model Marla Maples.

Donald met Maples at a 1985 celebrity tennis match, and according to a 1990 Vanity Fair feature, they became increasingly sloppy about hiding their reported romance. Donald and Maples were repeatedly spotted at the same events and she allegedly moved into a suite at the since-defunct Trump Regency hotel. However, their biggest misstep occurred in 1989 when both Ivana and Maples vacationed in Aspen, Colorado at the same time. The two women actually bumped into each other and, according to Ivana's 2017 memoir, "Raising Trump," Maples boldly let the truth fly. "This young blonde woman approached me out of the blue and said, 'I'm Marla, and I love your husband. Do you?'" Ivana recalled.

Ivana filed for divorce, and Donald married Maples in 1993. Despite the apparent overlap in their relationships, Donald later said in a 2022 deposition that he wasn't sure when he started seeing Maples. "It was towards the end of the marriage," he mused, per The Washington Post. "It could be a lap over, but I don't really know."

Donald Trump's 2024 presidential campaign was marred by controversy, but perhaps nothing stirred up as much talk as the legal trial tied to his alleged affair with Stormy Daniels. Trump first met the adult film star at a celebrity golf tournament in 2006 and, as she told 60 Minutes in 2018, he invited her to dinner. She agreed and met him in his hotel room where they ended up ordering room service. Daniels said she asked about Melania and Barron Trump, who was then just a few months old, and "he brushed it aside." She claimed they had sex that night, even though she wasn't attracted to Trump, but underscored, "I didn't say no; I'm not a victim."

According to Daniels, they continued speaking and saw each other again but had no more physical encounters. In 2011, she sold her story to a newspaper for $15,000, but it was never published — allegedly following threats from Trump's lawyer, Michael Cohen — and she received no money. Then, mere days before the 2016 election, Cohen reportedly offered to pay her $130,000 in return for signing an NDA, which she says she accepted.

The story eventually made news anyway when it was uncovered by The Wall Street Journal in 2018. Then things got worse for Trump when all those press headlines gave way to 34 felony charges, including falsifying business records to influence the 2016 election. In 2024, Trump was found guilty on all charges, but denied the allegations and vowed to appeal.

Before his alleged affair with Stormy Daniels, Donald Trump reportedly got cozy with former Playboy Playmate Karen McDougal. Trump's alleged mistress spoke with The New Yorker in 2018, saying she met Trump when he filmed an episode of "The Apprentice" at the Playboy Mansion in 2006. Melania Trump had given birth to son Barron just a few months prior, but she said that didn't stop an affair from blooming. According to McDougal, they had their first date — dinner in a private bungalow at the Beverly Hills Hotel –, soon after. The model later jotted down notes about their relationship on eight pages of paper which The New Yorker obtained. Of that first date, she recalled, "We talked for a couple hours — then it was 'on!' We got naked and had sex." She also noted that he tried to pay her but she refused. They kept meeting up, but secrecy was key. "Every time I flew to meet him, I booked/paid for flight + hotel + he reimbursed me," she wrote.

As time went on, she said she met some of Trump's family members and even visited his apartment in Trump Tower, where he notably pointed out that Melania had a separate bedroom. After nine months of sneaking around, McDougal ended the relationship in April 2007 because she she felt guilty. "If I could go back and do a lot of things differently, I definitely would," she told the mag. A Trump spokesperson clapped back, "This is an old story that is just more fake news."

Nikki Haley has publicly dissed Donald Trump more than once, which made rumors of a clandestine fling all the more surprising. In 2017, Haley was appointed as the ambassador to the United Nations under the Trump presidency. In 2018, journalist Michael Wolff published his headline-making book, "Fire and Fury," in which he wrote, "The president had been spending a notable amount of private time with Haley on Air Force One and was seen to be grooming her for a national political future." While he made no outright claims of an affair, it didn't stop others from doing so after they read that passage.

Well, Haley was having none of it. Speaking with Politico in 2018, she called the speculation "highly offensive" and "disgusting." Noting that people will always try to find a way to tear down a successful woman, she went on to debunk Wolff's claims, one by one. "I have literally been on Air Force One once, and there were several people in the room when I was there," she said. "I've never talked once to the president about my future and I am never alone with him."

Indeed, not only would Haley go on to campaign against Trump in 2023, but the two would regularly exchange jibes. "Chaos follows him," she once proclaimed at a South Carolina rally. Meanwhile, Trump giddily boasted about her eventual campaign suspension in 2024, writing on Truth Social, "Nikki Haley got TROUNCED last night."

While Donald Trump has faced an endless barrage of cheating allegations, Melania Trump has also made a few headlines of her own. It all started in 2017 when an author named Monica Byrne took to Twitter to claim that a secret source had told her Melania was having an affair — and Donald knew about it. In the since-deleted tweets, which were saved by Perez Hilton, Byrne alleged, "Word is, for many years, Melania's been having an affair with the head of security at Tiffany's in the Trump Tower lobby." She went on to claim that when Donald moved into the White House, Melania prolonged her stay in New York not because Barron Trump had to finish school (which was the official reason she gave) but because she wanted to be with her lover.

Jump to 2019 and podcaster Noel Casler (who once worked on "The Apprentice") appeared to corroborate those claims. "Melania didn't live with him in Trump Tower either, she lived with her boyfriend," he tweeted. "We had to book the transport on 'Apprentice' finales and her pick-up was NOT on 5th Ave." Political Flare later identified the mystery man as Henry "Hank" Siemers, the vice president of global retail security for Tiffany & Co.

Like father, like son. In 2011, Donald Trump Jr. allegedly began an affair with Aubrey O'Day while his then-wife, Vanessa Trump, was pregnant with their third child, Tristan. The pair met while O'Day was a contestant on "The Celebrity Apprentice" and he was acting as an advisor on the show. A fling soon began and while an insider later told Page Six, "I think his marriage to Vanessa was over long before Aubrey came along," that may not have been entirely true. Not only did Vanessa and Don Jr. remain married until 2018, but they actually had two more kids together: Spencer in 2012 and Chloe in 2014. Indeed, one source told People that when Vanessa found out about the affair in 2012, Don Jr. quickly ended it. "Aubrey was very, very into Don," they claimed. "He liked her, but she was definitely more keen on him."

The drama first made headlines during the 2018 divorce, then resurfaced in 2022 when O'Day decided to share her side of the story. "We both thought we were each other's soulmates," she told People. She shared a similar sentiment with Page Six, professing, "I'll always have love for him." The singer said the breakup was difficult, and it didn't happen because of a lack of affection. "I saw him choose a life that was inauthentic — for status, power, whatever it is," she said. "I'm so disappointed in what he became."

Controversy hasn't just been reserved for the most well-known members of the Trump family. In 2021, Pulitzer Prize-winning Washington Post reporter Carol Leonnig published a book titled "Zero Fail: The Rise and Fall of the Secret Service" in which she made some serious allegations against Vanessa and Tiffany Trump. According to insider sources, both Trump's youngest daughter and Donald Trump Jr.'s ex-wife had gotten "inappropriately — and perhaps dangerously — close" to Secret Service agents. This reportedly occurred while Donald Trump was in office between 2017 and 2021.

First, there was Vanessa, who is said to have started dating one of the agents assigned to protect her family. It's not known when their supposed union would have started, but she only filed for divorce from Don Jr. in March 2018, and it wasn't finalized until February 2019, so there is the possibility of an overlap.

As for Tiffany, Leonnig wrote that "She began spending an unusual amount of time alone with a Secret Service agent on her detail." It's unclear if they would have still been a thing when she met her future husband, Michael Boulos, in 2018, but a spokesperson for Tiffany denied the reports. "This is nothing more than gossip," she told The Washington Post. "Tiffany's experience with the Secret Service was entirely professional."