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Donald Trump Jr. Reportedly Had an Affair with Celebrity Apprentice Cast Member Aubrey O’Day


Donald Trump Jr had an affair with singer Aubrey O'Day, reports Perez Hilton.

That romance nearly caused Don Jr and wife Vanessa to divorce back in 2012 according to multiple sources, who said that the pair began their relationship when O'Day appeared on Celebrity Apprentice.

Those same sources said that O'Day only agreed to the relationship because Don jr told her that he and Vanessa were in the process of separating at the time.

'Apparently, the 40-year-old was very aggressive in pursuing the former Danity Kane artist - telling Aubrey he loved her and that he wanted to be with her,' reports Perez Hilton.

The affair began in 2011 and lasted until March 2012 according to reports.

Multiple reps for The Trump Organization did not respond to a request for comment.

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Affair: Aubrey O'Day reportedly had an affair with Donald Trump Jr while the pair worked together on Celebrity Apprentice (pair above on set)

Pursuit: 'Apparently, the 40-year-old was very aggressive in pursuing the former Danity Kane artist - telling Aubrey he loved her,' claims Perez Hilton (O'Day and Don Jr on set in 2011)

Meet and greet: O'Day (far left) and Donald Trump Jr. (center with back to camera) on the set of Celebrity Apprentice in October 2011

Monday afternoon O'Day shared a selfie in her underwear to Instagram with the caption: 'I’m only interested in the things money can’t buy'

O'Day had previously hinted at having some damning information about the Trump family following the election.

In the wake of President Trump's win the 34-year-old singer wrote: 'I’m embarrassed to be an American.'

When a follower then pointed out she had appeared on Trump's reality show, O'Day replied: 'No. my story I didn’t tell is worth millions now … this doesn’t hurt me, it hurts America.'

O'Day later deleted that second tweet.

The tweet still managed to spark rumors of a possible affair between O'Day and one of the Trump men, though no concrete evidence has ever been provided to prove that there was any relationship.

Shortly after Perez Hilton broke the story, Page Six released new details and confirmed others about the alleged affair.

'It was him who chased her,' said one source familiar with the situation.

'He told her that his marriage was already in the process of dissolving.'

A second source claimed that it was Don Jr's father who had to eventually step in and tell his son to 'knock it off,' encouraging him to return to his wife Vanessa.

New baby: Vanessa had just given birth to her third child, son Tristan, when the alleged affair began in 2011 (Don Jr and Vanessa in September 2011 above)

Baby on board: Vanessa then became pregnant with her fourth child, son Spencer, when the affair was allegedly taking place (Don jr and Vanessa above in May 2012)

Fun and games: It was President Trump who reportedly told Don Jr to ;knock it off' and return to his wife (Trump and O'Day on the set of Apprentice)

A star is born: O'Day rose to fame thanks to her time on the MTV show Making the Band (left in 2005, right in 2006)

The Page Six report also reveals that sources told them O'Day was very much in love with Don Jr and never after his money.

She also never received any money from him to keep quiet according to those same sources.

Late Monday afternoon O'Day shared a selfie in her underwear to Instagram with the caption: 'I’m only interested in the things money can’t buy.'

In October of 2011, Vanessa gave birth to the couple's third child, son Tristan.

She then became pregnant in early 2012 before giving birth to son Spencer in October of that year.

She was reportedly 'devastated' when her husband said he planned to leave her for the singer.

O'Day shot top fame back in 2005, the same year that Don Jr and Vanessa were married at his father's Palm Beach estate, Mar-a-Lago.

She was a contestant on the MTV program Making the Band, and selected by Sean 'P Diddy' Combs to become part of the girl group Danity Kane.

The group enjoyed a successful run in the aughts, at which time their first two albums debuted at the top of the charts.

They also had a number of hit singles, with their song Damaged charting in the top ten on Billboard and earning the group two MTV Video Music Award nominations in 2008.

O'Day had split from the group by that point and her solo efforts failed to repeat the success she had with Danity Kane.

Then, in 2012, she was back in television on Celebrity Apprentice.

O'Day also managed to grab headline over the years for her life outside the recording studio, dating Jersey Shore star Paul 'Pauly D' DelVecchio, DJ Cassidy and Evan Ross.


It’s pretty unfair how often we’re forced to think about the sex lives of the various philandering Trumps, but here we are again, this time, with Don “The Other Rat Face” Jr. and Danity Kane member Aubrey O’Day. Get your sick bags ready, everyone, because this actually gets worse: There’s reason to believe she may have written a song about him in 2013.

Don-o reportedly fell in love with O’Day while she was a guest on Celebrity Apprentice in 2011. He was an “adviser,” and at some point, while his wife Vanessa was pregnant with their fourth child (classic), the two rubbed nethers several times until March of 2012. A year later, this song popped out. It’s called “DJT.” That could stand for anything but let’s be honest, it probably doesn’t.

The lyrics are the stuff of an overwrought nightmare; the sort of thing a 15-year-old writes on her LiveJournal and then reads at an open mic years later for laughs. You can read the whole thing here, provided your stomach can withstand the idea that a flesh-and-blood human felt so moved by DJ’s puckered face (and accompanying genitals) that she was compelled to sit down and pen...whatever this is. Honestly, I couldn’t even get through the whole thing—there’s a lot about walking?

Here’s how it ends:

You’re the only one who ever knew my heart

I have to move on, I need your help I can’t believe that this was all a lie You have to tell me you love me I don’t ‘cause you’re a fucking pain in my ass Tell me you love me and I won’t talk to you anymore I’ll leave you alone Look, it doesn’t matter, it can’t matter The truth will only kill us both You have to say it once to yourself and to me and then I’ll go I love you Talk to you later

Vanessa filed for divorce in Manhattan Supreme Court last week, though a source familiar with the “situation” asserts that “I think his marriage to Vanessa was over long before Aubrey came along.” You don’t say!


It’s the Trump family-Danity Kane crossover news the world has been waiting for: Donald Trump Jr. reportedly had an affair with Aubrey O’Day. According to Us Weekly, which confirmed the news with multiple anonymous sources, Trump and the former Celebrity Apprentice cast member met while filming the reality series, with their relationship spanning from the end of 2011 to March 2012.

According to a source close to O’Day, Trump had told her that he was separating from his wife, Vanessa, and that he no longer loved her, “all of that stuff.”

“Aubrey fell for him hard,” said the source. “She thought they were going to be together for real.”

In March 2012, just months after having their third child, Vanessa Trump reportedly found e-mail exchanges between her husband and O’Day, causing him to call off the affair. A source told Page Six that Trump Sr. also intervened when he heard about the relationship with O’Day, telling his son to “knock it off.” The couple would go on to have two more children together, their son Spencer Frederick and daughter Chloe Sophia.

Since the alleged affair has come to light, Internet sleuths (and die-hard Aubrey O’Day fans, too, probably?) have unearthed a not-so-subtle 2013 song from the singer called “DJT,” about a man who calls to break up with his mistress.

The loss of Donald Trump Jr. must be more difficult than we could ever imagine.

O’Day also hinted at her relationship with the now-president’s son after Donald Trump won the election. The Hillary Clinton supporter tweeted that she was “embarrassed to be an American” and that “You can be a lying, abusive piece of trash that is personally and publicly racist, sexist & homophobic and run our country.” She then responded to followers asking her why she didn’t stand up against Trump while she was on Celebrity Apprentice, writing: “My story I didn’t tell is worth millions now . . . this doesn’t hurt me, it hurts America.”

Vanessa Trump filed for divorce from Donald Trump Jr. last week, releasing a statement saying, “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.”

Since then, reports about their troubled marriage, including Trump Jr.’s, uh, thrifty habits, and Vanessa’s “ill thug” past, have resurfaced.

So . . . has anyone asked Diddy what he thinks about all this?


Photo: Frederick M. Brown/Getty Images

On Monday reports emerged claiming Donald Trump Jr., currently embroiled in a divorce from wife Vanessa, allegedly had an affair with singer Aubrey O’Day roughly six years ago. The pair allegedly met while O’Day was a contestant on Celebrity Apprentice in 2011, competing under the watchful eye of the current president. While neither O’Day nor Trump have commented on the reports so far, there is the little matter of the first song on the former Danity Kane member’s 2013 album Between Two Evils.

Entitled “DJT,” the half-electronic-torch-song/half-extremely-long-phone-call features a conversation between O’Day and a former lover, a man who has left her behind to return to his regular life. “I’ll always want you and always wonder about it,” he explains. “But it doesn’t matter because I have to stay here.” So, is the song really about Donald John Trump Jr., or is it about another person with the initials DJT? The world will never know, which is honestly exactly how much the world should know about this entire situation.

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