O'Day and Trump Jr. reportedly began their affair while filming season 5 of Celebrity Apprentice. Sources have told Us Weekly that it lasted from the end of 2011 to some time in March of 2012. On the first day of the following month, O'Day tweeted a photo of a pregnancy test with a positive reading.
"Ive been nervous to tell u this tweets, its been 3 1/2 months n hiding..But, I'm PREGNANT! Hope my baby is fearless!"
Ive been nervous to tell u this tweets, its been 3 1/2 months n hiding..But, I'm PREGNANT! Hope my baby is fearless! pic.twitter.com/RulO08ii— Aubrey O'Day (@AubreyODay) April 1, 2012
Later in the day, O'Day admitted that the tweet was a joke. "Hah I love april fools day!" she wrote while quoting a tweet from a fan who enjoyed the gag.
She clarified two days later at a Crystal Light event at Trump Soho Hotel.
"I've always been a huge fan of April Fool's Day," she confessed to Us Weekly.
Hah I love april fools day! “@Brittney_Shante: Wow lmao, well my first prank was from a damn celebrity! I really thought she was pregnant!!”— Aubrey O'Day (@AubreyODay) April 1, 2012
“I just thought that the pregnant joke would be the most fun, and to be honest, it’s just something I’ve been thinking about a lot more recently,” O’Day continued. “I’m getting to that age where my hormones are going and I’m looking for that … the joke just seems relevant.”
The singer's friends have now told reporters from multiple outlets that the joke was relevant for many reasons. O'Day and Trump Jr. were embroiled in a passionate affair where they were in constant communication. She was reportedly led to believe that he was separating from his wife, and he planned to be with her in earnest. When they broke up, insiders say she was devastated.
“The way he positioned it to Aubrey was that he and Vanessa were already on the outs,” a source close to production on Celebrity Apprentice told the outlet, adding that the two were “spending a lot of time together.”
“He called her all the time and really cared about her. He was giving her a lot of advice on her career. She’s actually a bright girl, way smarter than people realize,” the insider said.
The affair reportedly ended when Trump Jr.'s wife, Vanessa Trump, discovered their email exchanges, which friends say weren't particularly discreet. The couple reconciled for a time; however, on March 15, 2018, Vanessa filed for divorce.
“After 12 years of marriage, we have decided to go our separate ways. We will always have tremendous respect for each other and our families,” the estranged couple said in a public statement. “We have five beautiful children together and they remain our top priority. We ask for your privacy during this time.”