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Vanessa Trump Confronted Aubrey O’Day (With Her Kids Listening), A New Report Claims

by Jessicah Lahitou
Charley Gallay/Getty Images Entertainment/Getty Images / Grant Lamos IV/Getty Images Entertainment/Getty Images

Vanessa and Donald Trump Jr. have filed for divorce, and if recent headlines are accurate, infidelity may have played a role in the marriage's demise. According to an exposé in Us Weekly, several years ago Vanessa Trump confronted Aubrey O'Day over an alleged affair with Don Jr. Bustle has reached out to O'Day's representatives and Vanessa's lawyer for comment.

According to Page Six, where news of the affair originally appeared, the two reportedly began seeing each other in 2011 during O'Day's stint as a contestant on Celebrity Apprentice. But in early 2012, after finding an email "treasure trove" between her husband and the singer, Vanessa called the Danity Kane singer and reportedly asked her to quit the tryst. Sources say Vanessa had her children on the line when she made the call, ostensibly to further persuade O'Day not to tear apart the family.

An O'Day insider told Us Weekly that their affair was "intense," with O'Day reportedly believing that she and Don Jr. would eventually "be together for real." According to the source, Don Jr. said he was going to leave Vanessa.

But it wasn't Vanessa's impassioned plea that ended O'Day's affair with Don Jr., said the insider. Rather, Donald Trump (the future POTUS himself) stepped into the drama and convinced his eldest son to walk away from O'Day. A separate Us Weekly article stated Vanessa and Don Jr. were "reconciled" after the incident.

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Speculation about the affair has circulated for a while. On election night, Page Six reports that O'Day tweeted, “my story I didn’t tell is worth millions now.” But sources told the magazine that O'Day's feelings for Don Jr. were real, which would explain in part why she never sold her story or went public with the details.

It seems O'Day had reason to believe her relationship with Don Jr. would evolve. An insider told Page Six that Don Jr. had been the one pursuing O'Day. “He told her that his marriage was already in the process of dissolving," they said.

Vanessa and Don Jr. now have five children together, two of whom were born after the reported affair took place. Vanessa filed for divorce in New York on March 12, but neither she nor Don Jr. have yet spoken publicly about their reasons for parting ways. They did release joint statement that read:

We will always have tremendous respect for each other and our families. We have five beautiful children together and they remain our top priority. We ask for your privacy during this time.
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Don Jr. will be the first of President Trump's children to get divorced. Ivanka Trump and her husband, Jared Kushner, have been married for over eight years, while younger brother Eric Trump tied the knot with his wife, Lara, in 2014. At 24 years old, Tiffany Trump has never been married.

President Trump got divorced from his first wife, Ivana, in 1992. Given the public profile of the New York real estate mogul, his marriage's downfall would almost certainly have been tabloid fodder regardless of the circumstances. But the Trump divorce proceedings were notably dramatic — even Ivana described the ordeal as "insane" in an interview with The Guardian.

The divorce was preceded by the very open affair Trump carried on with Marla Maples. "I couldn't turn on the television without hearing my name," Ivana told The Guardian. Her split with Trump spawned perhaps the most famous line of advice ever given to women in a similar situation. Ivana summed up her approach in the immortal imperative: "Don't get mad. Get everything!"

With media following every detail of Don Jr. and Vanessa's divorce, it looks like history may be doing a bit of repeating.