Donald Trump Jr. Had Aubrey O'Day's Other Exes Beat When It Came To This One Thing

Donald Trump Jr.'s relationship with Vanessa Trump was arguably one of the most troubled Trump family marriages and ended, as most of their unions do, because of an alleged affair. His reported mistress was former "Celebrity Apprentice" contestant and pop star Aubrey O'Day, who hasn't exactly tried to keep their tryst under wraps. In fact, she's praised Don Jr. for being one of the nicest guys she's ever dated. "Don Jr. made me feel the most beautiful," O'Day gushed to Us Weekly in July 2025. "He made me feel the smartest and the most beautiful, but he loved my mind more than anything else, and that's what I love about me. The way that we loved was we loved the same." The Danity Kane member added that her other famous ex, reality TV personality Pauly D, couldn't hold a candle to Don Jr. either.

As she sadly recalled, "[He] definitely brought me down all the time and made sure that I didn't have, like, high self-worth." Needless to say, that relationship didn't last, with the "Jersey Shore" star admitting to Page Six in 2018 that he was glad to have broken up with O'Day. "The way I feel is I dodged a bullet. I'm glad that I was out of that whole situation," Pauly D said at the time. Naturally, her Us Weekly interview received a lot of attention, and the singer quickly clarified the praise she'd heaped onto Don Jr. on her Instagram Stories. "To address all the DM's on this article once.. To be CLEAR — I loved the man he almost became. But loyalty & desires for power twisted that path," O'Day proclaimed (via TooFab).

If Aubrey O'Day is to be believed, her affair with Donald Trump Jr. began in 2011 and ended rather abruptly in 2012. Notably, this was the same year Vanessa Trump reportedly found out Donald Trump Jr. was cheating when she discovered sultry text messages between him and the "Making the Band" star. Donald Trump reportedly also knew about Don Jr.'s affair with O'Day and wasn't happy about it, but the sordid tryst only made headlines in 2018, several years after it actually occurred. It could have served as additional ammunition for Hillary Clinton's 2016 presidential campaign, but the public never knew about it. Helpfully, O'Day provided an explanation as to why that is. While making an appearance on the "Sofia with an F" podcast, in 2023, she claimed that Trump's former lawyer and fixer, Michael Cohen, is the real reason the affair didn't become public knowledge until 2018. 

"I spent likely a decade or something, maybe a little less than that, covering it up with Michael Cohen," O'Day disclosed. Indeed, a source confirmed to the Wall Street Journal, also in 2018, that Us Weekly had a credible source feeding them intel on the alleged relationship in 2013 and was ready to publish the bombshell story when Cohen intervened and threatened a lawsuit. "We were all on speakerphone and huddled around the phone," the source divulged of the conversation with Cohen. "He was just one of these New York characters where he was just like swearing at us and totally over-the-top threatening." In the end, Us dropped the story. But as the old adage goes, the truth always comes out.