Politics Donald Trump Jr. Cheated on Wife Vanessa with Former 'Apprentice' Contestant Aubrey O'Day: Report Donald Trump Jr.'s marriage began its downward spiral in 2011 when he reportedly cheated on wife Vanessa with former Danity Kane singer and Celebrity Apprentice contestant Aubrey O'Day, according to Page Six By Tierney McAfee Published on March 20, 2018 03:30 PM Share Tweet Pin Email Donald Trump Jr.‘s marriage began its downward spiral in 2011 when he reportedly cheated on wife Vanessa with former Danity Kane singer and Celebrity Apprentice contestant Aubrey O’Day, according to Page Six. The outlet, which on Thursday broke the news that Vanessa had filed for divorce after more than 12 years of marriage, now reports that President Donald Trump’s eldest son “fell for” O’Day while he was serving as an adviser for Celebrity Apprentice in 2011. Page Six cited anonymous sources who said that Trump Jr., 40, and O’Day, 34, a former singer in the girl group Danity Kane, had rendezvous in multiple cities during their alleged affair and wrote each other love letters. The sources also said that Trump Jr. told his wife he planned to leave her for O’Day and that Vanessa was “devastated” by the news. David Buchan/Variety/REX/Shutterstock; Ida Mae Astute/ABC/Getty As Page Six notes, Vanessa was pregnant with the couple’s son Tristan around that time. The couple share five children together: Kai Madison, 10, Donald III, 9, Tristan, 6, Spencer, 5, and Chloe, 3. Trump Jr. “pursued [Aubrey]. It was him who chased her,” a source familiar with the situation told Page Six. “He told her that his marriage was already in the process of dissolving. I think his marriage to Vanessa was over long before Aubrey came along.” The source added that Trump Jr.’s family “pressured” him to stay with Vanessa, while another source said the older Donald Trump knew about the alleged affair and told his son to “knock it off.” A third source said the alleged affair marked the beginning of the end for Trump Jr.’s marriage and said Vanessa planned to leave her husband then. Larry Busacca/Getty On election night in November 2016, O’Day tweeted that “my story I didn’t tell is worth millions now.” But sources told Page Six that O’Day — who rose to fame on Sean “Diddy” Combs’ MTV reality series Making the Band — was in love with Trump Jr. and was never paid to stay silent by the Trumps. Speculation swirled on Tuesday that O’Day may have hinted at the alleged fling with her song “DJT” from her 2013 album Between Two Evils. The letters “DJT” are Trump Jr.’s initials. RELATED VIDEO: Donald Trump Jr.’s Wife Vanessa Files for Divorce After 12 Years of Marriage O’Day sings of lost love in the song, which includes lyrics like: “Whatever the truth is defines the reality of you and I forever/And I need to be able to define that before I can walk away/I thought it was forever at the time but maybe I was lying to myself.” O’Day’s manager, Steven Grossman, told PEOPLE that she is not commenting at this time. A spokesperson for Trump Jr. did not immediately respond to PEOPLE’s request for comment. Trump Jr. also made headlines last week for his past racy Twitter exchanges with former model Melissa Stetten. “Surprised his marriage didn’t work out since he was sending me DMs a month after his wife gave birth,” Stetten tweeted, also sharing screen shots of Trump Jr.’s messages to her from November 2011. A spokeswoman for Trump Jr., Amanda Miller, provided the full thread of their DMs, which she said showed that the exchange was just a joke.