Aubrey O’Day Dating History: Donald Trump Jr. And Other Ex-Boyfriends

Days after Vanessa Trump filed for a divorce from her husband of 12 years, Donald Trump Jr., reports of the president’s first born son having an affair with singer-songwriter Aubrey O’Day surfaced Monday.

Multiple anonymous sources told US Weekly that Trump Jr. had an extramarital affair with O’Day from late 2011 to March 2012. However, the couple has not listed the affair as the reason behind their split.

“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. We have five beautiful children together and they remain our top priority. We ask for your privacy during this time,” the couple said in a statement.

Donald Trump Jr. Donald Trump Jr. along with his wife Vanessa Trump attend the evening session on the fourth day of the Republican National Convention at the Quicken Loans Arena in Cleveland, Ohio, July 21, 2016. Photo: Getty Images/ Jeff Swensen

O’Day is believed to have met Trump Jr. on the sets of “Celebrity Apprentice” season five. One of her songs called “DJT” is believed to have been a tribute to her affair with him.

“You want to go back and live in the life that you had have forever? … I’ll always want you and always wonder about it but it doesn’t matter because I have to stay here. What made you stop believing in our world?” a section of the lyrics read.

O’Day has had an array of boyfriends and rumors relationships in the past, the most recent one being former “Jersey Shore” star Pauly D, whom she dated for one and half years before calling it quits last year.

Both of them participated in the celebrity reality show “Famously Single” and they became romantically involved in season one of the series. It was rumored that the O’Day was pressurizing Pauly D to marry her and he was not ready for commitment.

“Well, I want a ring like ASAP! I think I put enough pressure for that to be going down sooner not later. I’m looking for something serious and I’m ready to move to the next chapter in my life where I’m a wife and a mom and to experience other things than what I’ve been doing my entire career. He knows that and we made sure that’s the page we were both on in the beginning,” O’Day later told E!

O’Day also took part in another reality show called “Marriage Boot Camp: Reality Stars” in 2015, with her the-then boyfriend former boy band member Travis Garland, who was six years older than her. Despite all their efforts in the show, the couple broke up in June of the same year, Heavy reported. 

Boy band New Kids on the Block member Donnie Wahlberg was one of the first celebrities O’Day was linked to in 2008. After both of them attended the premiere of the thriller movie “Righteous Kill,” they were rumored to be romantically involved, although neither of them confirmed the relationship.

They did, however, go on to collaborate a year later on a song called “I Got It.”

Voted Thanks!

What's On Your Mind?