The Biggest Romance Rumors To Ever Surround Donald Trump Jr.

Donald Trump Jr.'s father was once a tabloid fixture due to his infidelity, and now it's the heir's turn to have his love life sensationalized by celebrity gossip mags. While Donald Jr. has willingly followed his father's footsteps into the businesses of dealmaking and politics, having everyone all up in his romantic business is one way he may not want to emulate daddy dearest.

Donald Jr. admitted that he hated reading about Donald Trump cheating on his mother, Ivana Trump, with Marla Maples. He was a tween at the time, and the tawdry tabloid headlines provided his classmates with plenty of fodder to tease him. "Being driven into school every day and you see the front page and it's divorce! THE BEST SEX I EVER HAD! And you don't even know what that means," he lamented to New York Magazine. Eventually, his own amorous exploits caught the attention of gossip columnists. Page Six writer Chris Wilson once observed a cringeworthy interaction between Donald Jr. and Paris Hilton. "Donald Trump Jr. was like leaning over and trying to paw her and she's looking at me, holding on to me like a cat holding on to the side of a tree," Wilson recalled to Vanity Fair. "You know, like, 'Please help me.'" However, he seemingly wasn't an interesting enough subject back then; a photo of Donald Jr. and Hilton captioned "Art of the Feel" went unpublished. It wouldn't be until he got engaged that he began making regular tabloid appearances.

When Donald Trump introduced Donald Trump Jr. to model Vanessa Trump (née Haydon), he did it twice at the same event because he'd forgotten that he'd already done it. Weeks passed before Donald Jr. and Vanessa crossed paths again at a party, and their love story began with the uttering of an ableist slur. "You're 'the one with the re***ded dad!'" Vanessa recalled saying, per The New York Times.

When the couple got engaged in 2004, the New York Post labeled Donald Jr. a "cheapskate" for popping the question in front of a jewelry store at a mall. A source told the outlet that Donald Jr. had gotten Vanessa's engagement ring for free after agreeing to give the store some publicity by choosing it as the location of his proposal. Donald Trump later confirmed this rumor to be and revealed that he gave his son a stern scolding over the bad optics.

Donald Jr. was accused of being cheap again when he and Vanessa got divorced in 2018. "He gives her very little help and has been keeping her on a tight budget," a source told Page Six. "She doesn't live a lavish life and can very rarely pick up a check at dinner." The insider claimed that Vanessa had even started borrowing money from her mom to pay her bills. However, a rep for Vanessa denied that money was the cause of the split.

Donald Trump Jr.'s rumored extramarital affair with Danity Kane member Aubrey O'Day got so much attention that Ivana Trump even decided to weigh in on her son's cheating scandal. How humiliating is that? 

In 2018, Page Six reported that Donald Jr. fell for O'Day when she appeared on "The Celebrity Apprentice" in 2011. A source claimed that the "Triggered" author told the singer that he and Vanessa Trump had decided to end their marriage. However, according to other sources, Vanessa was not interested in getting a divorce; when she learned about her husband's affair in 2012, she reportedly set out to put a stop to it. "She called Aubrey with her kids on the phone," an insider told Us Weekly. Another source told Page Six that "Vanessa went gangster" during the call.

While Vanessa's guilt-bombing possibly played a role in O'Day and Donald Jr. ending their affair, O'Day found it difficult to move on. In 2022, she told Page Six that she believed Donald Jr. was her "soulmate." She also said of her feelings for him, "I love him. Love, loved, love. I'll always have love for him." O'Day revealed that the man she knew was nothing like the one who is now a fierce defender of his dad's political agenda, and she expressed her dismay over his transformation into someone she no longer recognized. "I saw him choose a life that was inauthentic," she stated.

In her book "Unhinged: An Insider's Account of the Trump White," former "Apprentice" contestant Omarosa Manigault Newman corroborates Aubrey O'Day's claim that she had an affair with Donald Trump Jr., revealing that she saw intimate photos and texts from the Trump son to the singer. According to Newman, she also witnessed Donald Trump advising his son to have an affair. She recalled the ex-president telling Donald Jr., "You got to get some a** like that," while he was reminiscing about a long-ago fling with model Carol Alt. But when the Donald learned that his boy had taken his advice, he was reportedly displeased. One source told Page Six that "The Apprentice" host warned Donald Jr. to "knock it off."

In her interview with Page Six, O'Day confirmed that Donald Jr.'s father had influenced his decision to dump her and remain married to Vanessa Trump in 2012. "He told me all the punishments that he was going to have to endure," she said. When Vanessa and Donald Jr. decided to separate in 2018, Donald reportedly attempted to meddle in his son's love life again by pleading with the couple to give their marriage another chance — but to no avail. "He's personally upset ... Donald Trump failed as (a) marriage counselor," a source told the Daily News. The split occurred when the Mueller investigation was still ongoing, and the insider suggested that Donald was concerned about what Vanessa might tell investigators.

After Donald Trump Jr.'s marriage ended, the father of five soon moved on with someone who seems to adore his dad as much as he does: former Fox News host Kimberly Guilfoyle. Her tenure with Fox News reportedly ended in disgrace the same year she and Donald Jr. went public with their relationship; according to The New Yorker, she was ousted after being accused of sexual harassment. But if a report by The Atlantic is accurate, this ugly stain on Guilfoyle's rep is not the reason why Donald Trump reportedly disapproved of his son dating her, nor did he have an issue with her previous marriage to one of his political foes, California Governor Gavin Newsom. One of Donald's former advisers told the publication that the senior Trump found Guilfoyle attractive, and his interest in whether she was single was suggestive of a desire to pursue her himself.

Sources also told The Atlantic that Donald didn't want Guilfoyle working in his administration and had refused to invite her to spend Thanksgiving with the Trump family in 2018. Having the hots for the former talking head, which would presumably make him uncomfortable around her and his son, was reportedly not Donald's only issue with the relationship. "Even he can tell the difference between the attractive women on Fox who have a little bit of substance, and those who will be derided as airheads," a former White House aide said.

One of the strangest details about Kimberly Guilfoyle and Donald Trump Jr.'s relationship might be Guilfoyle's rumored willingness to describe what goes on in their bedroom. With rumors that the Trump family wanted nothing to do with Guilfoyle persisting, Donald Jr.'s brother, Eric Trump, declared that she had at least one fan among her future in-laws. "I completely disagree with the narrative and happen to think the world of Kimberly," he told Page Six in 2022. But a year prior, an author had made claims about Guilfoyle that gave the Trumps a good reason to groan about her involvement in the family's political biz.

In his book "Frankly, We Did Win This Election: The Inside Story of How Trump Lost," author Michael C. Bender claims that Guilfoyle had a habit of oversharing details about her and Donald Jr.'s sex life. He writes that Guilfoyle told Republican donors that Donald Jr. "liked when she wore a cheerleading outfit and was a 'naughty boy' when she 'let him out of his cage.'" One fundraiser attendee elaborated to Politico that Guilfoyle owns a Dallas Cowboys cheerleader costume. But Aubrey O'Day isn't buying these sexy role-play stories. "If I ever showed up in an outfit in front of [Donald Jr.], he would literally make fun of me," she stated on the "No Jumper" podcast. She also said of Guilfoyle, "That's just not his type. And I know what that man loves."