Donald Trump Jr.‘s relationship history is quite rocky, to say the least. After getting divorced from Vanessa Trump in 2018, he began dating Kimberly Guilfoyle. Although he did get engaged to the Fox News host, their relationship met an unexpected end in December 2024. Although the real reason never came to light, according to sources, it was because of a third woman, Bettina Anderson, who would soon become his girlfriend.
Now, we all know about these three women’s relationship with Donald Trump Jr., more or less. But one woman many people didn’t know about was Aubrey O’Day. Sources allege that Don Jr. had a brief affair with the former Danity Kane singer when he was still married to his ex-wife, Vanessa Trump.
According to RadarOnline.com, O’Day herself claimed that the pair had an affair over a decade ago. It reportedly began in 2011, when the two became involved. At that time, Donald Trump Jr. was serving as an advisor on his dad’s show, Celebrity Apprentice. However, according to reports, the affair between Donald Trump’s first son and the singer ended when his then-wife discovered the text exchanges between them.
Donald Trump Jr. reportedly had an affair with Danity Kane alum Aubrey O’Day after she appeared on “Celebrity Apprentice” in 2011 https://t.co/473eSXvvcb pic.twitter.com/eHyVtbaIZZ
— New York Daily News (@NYDailyNews) March 19, 2018
It wasn’t until 2018 that the first rumor about the alleged affair came to light. At that time, one media outlet reported that Donald Trump Jr. even admitted to the infidelity and said that he would be leaving Vanessa for O’Day. It is important to note that Vanessa Trump was pregnant at that time, with Tristan Milos Trump.
According to a source’s account at that time, “His marriage to Vanessa was over long before Aubrey came along. [Don Jr.] pursued Aubrey. It was he who chased her. He told her that his marriage was already in the process of dissolving.” The insider also claimed that despite the chaos, a family member pressured him to “stay in his marriage” with Vanessa.
Donald Trump Jr. cheated on his wife with Danity Kane’s Aubrey O’Day, multiple sources confirm to Us Weekly. pic.twitter.com/UsXtlkn3e4
— Pop Crave (@PopCrave) March 20, 2018
In 2018, as his marriage ended, Aubrey O’Day spoke publicly about their alleged affair. During the season premiere of MTV’s Ex on the Beach, she, for the first time, referred to Don Jr. as her “ex.” However, later, she clarified that they were “each other’s soulmates.”
In an interview with PEOPLE, she said, “It’s something we spoke about often. A soulmate is someone you spend a period of time, a moment of life with, with whom you’re connected as one. I had that with Don.”
“There were tabloids and headlines and speculations and a lot of rumors – a lot of untrue things that were being printed continuously for a period of time, but no one ever just asked me directly what the truth was. When I was asked, I told the truth,” added Aubrey.
