The Complete Timeline Of Aubrey O'Day's Alleged Affair With Donald Trump Jr.

The sparks between Donald Trump Jr. and Aubrey O'Day began on the reality television show, "The Apprentice," which aired in 2012 after filming during the previous year. Thanks to the singer's lack of subtleness, rumors about their affair began soon after viewers began watching them on-screen together. In one episode, she admitted having a crush on him — even though he was married and had been for over five years. "Don Jr. makes me nervous because his opinion means a lot," she said. "He's done this for a very long time. And also, I have a very big crush on him, so I don't want to disappoint him."

We do not know if they had begun the alleged affair at the time the episode was filmed, but we know that their dalliance began towards the end of 2011 and got deep quickly. O'Day's social media posts (retrieved via BuzzFeed News) show that her secret relationship with an unnamed man was in full swing by November 2011. "Woke up in a room filled wall to wall with my fav flower, white lilies. You gave me a garden of love, baby," she tweeted that month. Her tweet came a month after Don Jr and his wife welcomed their third child.

Donald Trump Jr. has consistently ignored rumors of their affair, but thanks to Aubrey O'Day and other sources, we've got the general picture. The apparent lover boy was reportedly going through a rough patch in his marriage to Vanessa Trump and turned to an affair. O'Day hinted at secret getaways, grand gestures of romance, and even talk about their future together. She later alleged that Don Jr. told her he was leaving his wife and wanted to have kids with her.

In December 2011, she posted that she and her mystery beau designed her Christmas tree, and by May 2012, she shared that she had become a known face at "the Trump." When O'Day's curious Twitter fans pressed for details, she didn't give in: "He likes us to remain private, and I want everyone to know."

Eventually, O'Day got her wish when Vanessa Trump found out Donald Jr. was cheating. During an appearance on Michael Cohen's podcast in 2023, Aubrey O'Day claimed that Vanessa Trump had tried to end their relationship by posing as Don Jr. and texting her. "I don't love you anymore. We're canceling the trip. I love my wife. I don't want to be with you," Vanessa reportedly texted through Don's phone. 

Aubrey O'Day told Michael Cohen that Vanessa Trump called her multiple times to confront her about the affair. People also reports that Donald Trump Sr. learned of their affair and told Don Trump Jr. to "knock it off." Eventually, Don Jr. caved, and the musician's June 2012 post indicated problems in their paradise: "I hope [you] stalk my tweets and remember how much [you] loved me, and hate how weak you were to not fight for us. I know [you], they never will," she wrote. In one social media post from November 2012, she wondered how she could move on when her ex's "fingerprints [were] still on [her] heart." She told Michael Cohen that she needed months of therapy to get over the heartache.

In 2019, O'Day broke her silence on her alleged affair during the reality TV show "Ex on the Beach." She said, "I'm sending this message out to you, Don. Drop Kimberly [Guilfoyle, Don Jr.'s fiancé], she's crazy-looking. The White House f***ing little fiasco is about to be over, so why don't you come join me in the 'Ex on the Beach' house."

Needless to say, Don Jr. didn't heed that call. However, O'Day has continued to speak about their alleged affair. In 2020, she tweeted that Don Jr. hated his dad. Aubrey O'Day also made bold claims about Don Jr., Barron Trump, and other Trump family members. Two years later, she told Page Six that she would "always have love for him."