When Did Donald Trump Jr.'s Affair With Aubrey O'Day Really Begin?

Ever since Donald Trump first presidential run in 2016, his family's life has been on constant display — perhaps even at times when they wish it wasn't. The former president's eldest son, Donald Trump Jr., has found himself involved in some seriously scandalous situations, one of the biggest being his alleged affair with Aubrey O'Day.

The name O'Day may ring a bell because she was actually a member of the hit music group Danity Kane. Her celebrity status had her running in circles with other famous individuals, including, Donald Jr. The musician and political activist's rumored affair first came to light in 2018 when Page Six reported that an anonymous source claimed Donald Jr. had fallen for O'Day while still married to his wife, Vanessa. The source added that Donald Jr. was the one who "pursued [Aubrey]. It was him who chased her." They also revealed that Donald Jr. promised O'Day that his marriage was coming to an end. They said, "He told her that his marriage was already in the process of dissolving."

Days after the news of the alleged affair broke, O'Day reportedly told her friends that she did in fact have an affair with Donald Jr., per TMZ. Since then, O'Day spilled all the tea on the alleged affair and when it actually began.

Although the story broke in 2018, Aubrey O'Day and Donald Trump Jr.'s affair began long before major news outlets picked it up. According to Page Six, the affair began in 2011 after the Danity Kane singer appeared on Donald Trump's show, "The Celebrity Apprentice." Donald Jr. would frequently appear on the show as a financial advisor to contestants, which is how he and O'Day initially crossed paths. Despite meeting on the show, O'Day claims they weren't physically intimate until after the show wrapped.

The "Damaged" singer wasn't shy about sharing some personal details on Michael Cohen's podcast, "Mea Culpa," about her and the political activist's first time having sex. In fact, she revealed that she and Donald Jr. got intimate for the first time in a gay club. She claimed, "I was hosting a gay club, and our first time going out together — he wanted to see me so bad, and I was like, 'Well, I'm going to be at a gay club tonight.'" The location seems ironic as Donald Jr. has vocalized his dislike for the LGBTQ+ community in the past several years. However, the singer explained just how comfortable Donald Jr. was at the club as she shared, "I thought to myself, 'Man, you were super comfortable in that gay club' — in fact, so comfortable that we ended up going to the bathroom and, for the first time, had sex in a gay club bathroom."

With the news of Donald Trump Jr. and Aubrey O'Day's affair, it seemed like his marriage to Vanessa Trump was destined to end. According to People, the couple wed in 2005 and welcomed five children together. But, after how much they had been through, Vanessa wasn't about to give up even though Donald Jr. had cheated on her.

Us Weekly even claimed a source revealed that Vanessa contacted the Danity Kane singer in 2012 via phone call alongside her kids with the intention to keep the "Damaged" singer from her husband. A second source shared, "Vanessa went crazy and was super jealous." The romance between Donald Jr. and O'Day had reportedly gotten so bad that even his father, former President Donald Trump, had to step in. Donald had reportedly told his son to end his affair with the musician and instead focus on his marriage with Vanessa.

Donald Jr. and Vanessa tried to work on their marriage, but the resurgence of the news of the affair in 2018 seemingly became too much for the couple as they filed for divorce. According to People, they released a joint statement, sharing, "We are incredibly lucky to have five amazing children and are committed to raising them together. Our kids and their happiness will always be our first priority." By February 2019, Donald Jr. and Vanessa's marriage officially came to an end.