How Aubrey O'Day Claims Donald Trump Jr. Changed After Their Affair

In 2018, pop singer and reality TV star Aubrey O'Day and Donald Trump's son Donald Trump Jr. caused an uproar when it was revealed that the two had engaged in an extramarital affair between 2011 and 2012. The unlikely couple met on Season 5 of "Celebrity Apprentice." At the time, Trump Jr., a boardroom advisor on the series, was married to former model Vanessa Trump. O'Day and Trump Jr.'s relationship reportedly ended when Vanessa found explicit texts in her husband's phone.

In the years since their split, O'Day has openly discussed Trump Jr. and told Page Six that Trump Jr. chose to stay loyal to his father and his politics instead of being with her. Talking about the aftermath of their breakup, she said, "...I saw him choose a life that was inauthentic — for status, power, whatever it is." O'Day noted, "I'm so disappointed in what he became."

She also explained, "He was fiscally a Republican, but everything else was not, and for me, I just kind of saw him sell out, and I don't ever want him to see me sell out." Like his father, Trump Jr. is a devout conservative known for being vocal about these values on his social media, which have, at times, landed him in hot water. However, O'Day has been adamant that she saw a different side of Trump Jr. during their relationship.

In a 2019 interview with People, the publication asked Aubrey O'Day if she would ever consider reuniting with Donald Trump Jr. "I think he closed the chapter when he went the direction that he did," she revealed. "He's chosen to be in the life that he's in now and be the person that he is now, and that's not the person that I fell in love with." O'Day elaborated on this on Page Six. Calling herself a "social justice warrior," she noted that the Donald Trump Jr. she dated admired this aspect, but that she had doubts he would approve of this now.

In July 2023, O'Day went on "Mea Culpa," a podcast hosted by Donald Trump's former lawyer, Michael Cohen, and got candid about her affair with Donald Trump Jr. Per People, O'Day told Cohen that the pair first got intimate at a gay nightclub where O'Day was hosting a party. Notably, Trump Jr. has previously made several anti-LGBTQ+ statements. However, O'Day told Cohen that Trump Jr. did not seem uncomfortable at the nightclub.

Moreover, in an interview with Hollywood Life, O'Day disclosed, "I never saw him be ignorant. He was an incredibly brilliant man. I never saw him be a racist. I never saw him speak the way he does now."

Although their affair ended in 2012, Aubrey O'Day has referred to Donald Trump Jr. as her soulmate in various interviews. She told Page Six, "I love him. Love, loved, love. I'll always have love for him." In addition, she told the publication that their split took a toll on her and that she sought help from a therapist to help her heal. 

Despite the love, O'Day has no problem criticizing her ex when she thinks he's in the wrong. When Trump Jr. made a disparaging joke on Twitter in 2021, O'Day hit back. She tweeted, "You r so much more interesting than this petty nonsense. hurts to see u playing to your weakest self all the time." O'Day also slammed Trump Jr. on Hollywood Life, saying, "I was dating the man before the family chose to create what they created in order to take over this country. And the man that he's become is a ridiculous joke."

After their affair, Trump Jr. and his now ex-wife, Vannesa Trump, had a messy divorce that was finalized in 2019. He has since become engaged to attorney and former Fox News host Kimberly Guilfoyle. O'Day went on to have a relationship with Pauly D from "Jersey Shore" from 2016 to 2017.