Don Jr.in his role as “adviser” on the NBC show, fell for buxom Danity Kane star Aubrey O’Day while filming the  “Celebrity Apprentice” in 2011. Vanessa, who filed for divorce from President Donald Trump’s eldest son on March 15 after 13 years of marriage, was devastated when he told her that he planned to leave her for O’Day.
Vanessa was pregnant with their third child, Tristan, around that time.

Don Jr. and Vanessa Trump, divorcing after five children and 13 years of marriage

Don Jr. “pursued [Aubrey]. It was him who chased her,” allegedly telling her
“ his marriage was already in the process of dissolving.” Some observers however, believe “ his marriage to Vanessa was over long before Aubrey came along.”
In her most notable song from 2013, singer and former Playboy model-turned-reality TV contestant Aubrey O’Day pretends to talk on the phone with her lover as they break up. The track is titled “DJT,’’ apparently referring to her married ex-boyfriend, Donald John Trump Jr.

Donald Trump Jr and former pop star turned Playboy model O’Day had  a brief but ‘torrid affair’ after meeting on the set of ‘The Apprentice’ in 2011 

“You want to believe that everything with me was a lie? A fantasy? And you want to go back and live in the life that you had — have — forever?” O’Day says in the song. “You can say it was all a f–king fairy tale, or you can say it was real, but I need to know.’’
The man replies, “I’ll always want you, and I’ll always wonder about it, but it doesn’t matter because I have to stay here . . . I thought it was forever at the time, but maybe I was lying to myself.”
Reports of O’Day’s brief but torrid affair with the president’s eldest son broke Mar 19, just days after his wife of 12 years, Vanessa, filed for divorce. – Hours after the news of their affair surfaced, O’Day, 34, posted on Instagram what appeared to be a pointed message to Trump Jr., 40.
“I’m only interested in the things money can’t buy,’’ she wrote, beside a photo of herself in lingerie

Aubrey O’Day – “I’m only interested in the things money can’t buy’’
Until this week, O’Day was best known for her part in a made-for-TV band and for her reality-show appearances.
Her career was launched with a stint as the lead singer in an all-female band, Danity Kane, in 2005. The group, formed by rapper-producer Sean Combs for his MTV reality series “Making the Band,” had a couple of popular singles, including “Damaged,’’ before Diddy fired O’Day in 2008.
O’Day, subsequently gained notoriety when she gave a TV interview and spoke told a graphic story about her Spanx-ripping romance and Skype sex sessions with an unnamed lover whom she met on a TV game show. It was later revealed that she had an affair with married Donald Trump Jr. while appearing on “The Celebrity Apprentice” in 2011-12.

The next year, O’Day, a San Francisco native, was stripping for Playboy magazine.

Two years after that, she was cast for NBC’s “The Celebrity Apprentice,’’ hosted by Don Jr.’s dad, Donald Trump.
O’Day was vying on a show deep with talent such as singers  Clay Aiken, Debbie Gibson and Dee Snider, yet she made it to the penultimate episode before getting “fired.”
O’Day has said she was told during taping to up her sex game: “There were two female producers that came up to me, pulled me aside and said, ‘You’re running circles around everyone. We didn’t expect that from you,’ ’’ she said during a TV interview with Andy Cohen on the “Then and Now’’ show last year.
She went further to recount how the women explained: “Bottom line, ‘Trump doesn’t think you’re pretty,’ ” O’Day recalled.
“ ‘If you want to stay in the game, you need to follow these simple rules.’ And the rules were: Start parting my hair down the center, wearing it straight and pushing my t-ts up in tight outfits.”
O’Day went on to hook up with someone on the show, one of Trump’s on-air “advisers”.
Trump Jr. and O’Day would embark on an affair during the show’s taping, around the same time his wife was pregnant with their third child, it was later revealed.

Me and Mrs Jones: Star crossed lovers, Donald Trump Jr. and Aubrey O’Day on an episode of NBC’s “The Celebrity Apprentice”

It seemed to be the real deal for the illicit pair. – Sources say that the pair would meet up in various cities during their fling and wrote each other love notes. On election night in 2016, O’Day, pointedly tweeted, “my story I didn’t tell is worth millions now.”
A smitten Trump Jr. assured O’Day that his marriage was already all but over and promised to leave his wife for her. The younger Trump was said to have made promises to O’Day which left her walking on cloud nine. That is before Trump Sr. intervened, and reality set in. The president allegedly told his son to “knock it off’’ and  stay with his wife, as did other family members.
Vanessa would eventually learn her husband was having an affair through emails that she found between the pair, reports Us Weekly, and Trump Jr. finally agreed to give up O’Day.
Shortly afterward, O’Day tweeted that she was pregnant — then claimed she was just making an April Fool’s joke. She followed that up with a July 2012, posting of a recording of herself performing a remix of the song “Somebody That I Used to Know.’’
“Now and then I think of when we were together. Like when you told me that your marriage was a lie,’’ O’Day sings.
In December of that year, she also talked about what appeared to be another behind-the-scenes affair with a famous person.

Aubrey O’Day – Don Trump Jr’s  reality show romance comes back to haunt him after 7 years

O’Day told the podcast “RISK!’’ that she was once “filming a show and started up this unspoken connection with a big celebrity who I can’t name ’cause I’ll get sued up the a–.”
O’Day said that after shooting a “big performance,’’ she and the celebrity launched into a sex session in the bathroom — “all over, on top of this, under this, beneath this.’’
Their affair continued, she said  even though “we’re from different worlds.’’ Ending only when she caught him in his New York apartment with a naked woman.
The next year, O’Day recorded “DJT” for her album “Between Two Evils.’’
However, sources say that O’Day was truly in love with Don Jr., that she never sought money either to tell her story or to keep quiet, and that she was never paid by the Trump family.  On election night 2016, O’Day spoke upon Twitter against the former TV host’s victory. When some users suggested that she was just a sore loser for not winning on “Celebrity Apprentice,’’ she responded, “My story I didn’t tell is worth millions now.”
A source close to the divorcing couple said, “I think [Don Jr’s] marriage to Vanessa was over long before Aubrey came along.” A source close to the divorcing couple said, “I think [Don Jr’s] marriage to Vanessa was over long before Aubrey came along.”
Others acquainted with the situation believe that Vanessa “was going to leave [Don Jr.] then. That was the start of the downfall [of their marriage].”
Don Jr. and Vanessa have five children, and she filed for divorce last Thursday.