Inside Donald Trump Jr. and Aubrey O'Day's Relationship: Everything to Know — Including Their First Meeting and Alleged Affair

Aubrey O'Day has repeatedly claimed she had an affair with Donald Trump Jr. more than a decade ago.

They allegedly first hooked up in 2011, when Don Jr. served as an adviser on Donald Trump's show, Celebrity Apprentice. The entanglement reportedly ended when his then-wife, Vanessa Trump, discovered their text messages.

Reports about Don Jr. and Aubrey's alleged affair first surfaced in 2018.

One news outlet revealed Don Jr. admitted to his infidelity to Vanessa and told her she was leaving her for the former Danity Kane member. Vanessa was pregnant with their third child, Tristan Milos Trump, at the time.

"His marriage to Vanessa was over long before Aubrey came along," a source said at the time, adding that Don Jr. "pursued Aubrey. It was him who chased her. He told her that his marriage was already in the process of dissolving."

However, a family member reportedly pressured Don Jr. to "stay in his marriage."

In 2013, Aubrey released her album Between Two Evils, which included the track "DJT."

Some of the lyrics read, "I hate me for loving you/Hate you for letting our love die."

The song received renewed attention after her reported affair with Don Jr. emerged, with fans suggesting the title suspiciously referenced his initials. Aubrey never confirmed the connection between "DJT" and Don Jr.

Months after Don Jr. and Vanessa's divorce was finalized in 2018, the "Automatic" singer opened up about the alleged affair for the first time.

During the season premiere of MTV's Ex on the Beach, Aubrey referred to Don Jr. as her "ex" before calling him her "soulmate."

She later clarified her comments in an interview, saying they both thought they were "each other's soulmates."

"It's something we spoke about often. A soulmate is someone you spend a period of time, moment, of life with that you're connected as one. I had that with Don," Aubrey told People.

When asked why she opened up about the affair, she said she only answered "honestly" because she is "an honest person."

Aubrey added, "There were tabloids and headlines and speculations and a lot of rumors — a lot of untrue things that were being printed continuously for a period of time, but no one ever just asked me directly what the truth was. When I was asked, I told the truth."

In a series of tweets in 2020, the "Hurts So Good" songstress alleged Don Jr. tried to have a baby with her while they were having an affair.

"I definitely give great head.. but he absolutely loved me and was trying to have a baby with me (again, I have receipts), so I'm pretty sure the delusional one here is you. 🥴," one of her posts read.

Shortly after revealing Don Jr.'s past desire to have a baby with her, Aubrey alleged the businessman discussed releasing her NSFW photos to silence her.

"Conspire against? wait.. isnt that the same thing you did to me when you discussed having a thumb drive of naked pictures and information about me that could be released in order to silence & discredit me if need be?" she dropped the bombshell in a tweet, responding to Don Jr.'s post about "the highest levels of government" conspiring against his father.

In January 2021, Aubrey alleged she and Don Jr. "did drugs together" as she leveled more claims about her famous ex and his family.

"since trump has now lowered this debate to trashing family.. -don jr HATES his father. -ivanka [Trump] is a lesbian on the low. -eric [Trump] f----- miss universe on the apprentice board room table while with his now wife. #Debates2020," she wrote.

Aubrey, however, noted they never used cocaine.

"He never showed any interest. so I can't say that," she wrote amid speculation that the president's son was using the stimulant drug.

The "Before I Drown" singer has continued to unleash attacks on her alleged former flame in the years after their affair ended.

In a 2022 interview, she insisted she "wasn't dating the man" the public was "all seeing today."

"I was dating the man before the family chose to create what they created in order to take over this country," Aubrey shared, adding Don Jr. transformed into "a ridiculous joke" amid the process.

While she felt "so sad" about the person he had become, she did not think Don Jr. "had much of a choice."

Speaking in a December 2022 interview, Aubrey declared she would always have love for her "soulmate."

"But I saw him choose a life that was inauthentic — for status, power, whatever it is," said the singer, who reportedly felt "so disappointed in what he became."

"When I say that [he] was my soulmate, I'm not going to lie. I'm a very honest person, so I'm not going to say, 'Oh, I had nothing to do with him. He's ridiculous.' Like, no, he was just like me," she spilled.

Aubrey reportedly witnessed how Don Jr.'s desire for a platform "turned him into a different human."

She continued, "I've literally been that since I was young, and I've always been heavily empathetic. I have a bleeding heart, and I stand up for people that don't have a voice. And when I have it, I will use as much of it as I can to push agendas for people that deserve to be seen. And he loved all of those things about me. And the man you're seeing now probably wouldn't."

During an interview on Michael Cohen's "Mea Culpa" podcast, Aubrey alleged she and Don Jr. had their first hookup while she was attending an event at a g-- club.

"This is one of the biggest g-- parties in New York and everyone is in a G-string or less. I was just in my soul. There is no way that the man I've seen suited up for the past couple of months is going to show up here to see me in this lovely land I get to be in, and he did," she recalled. "My assistant said he was very comfortable and she remembered him being totally chill and nice with everybody. I looked at his Instagram for the first time in years the other night and saw all kinds of jokes and kind of belittling the g-- community, transgender women, etc. I thought to myself, 'You were super comfortable in that g-- club.' In fact, so comfortable that we ended up going to the bathroom and for the first time had s-- in a g-- club bathroom."

The pop star claimed, "I had spanx going from my throat down to my knees because I was suited up for some press or whatever we were doing that day, and I wanted to be extra tight and skinny. He could not get these things off of me for the life of him. He found a way to work around them and for the rest of our relationship, he called me spanky because of these spanx that otherwise would be one of the most humiliating stories ever, but it was very much him and I."

Opening up about her past relationships, Aubrey said Don Jr. and her other ex DJ Pauly D are not in the same league.

"The fact that I do interviews and they say, 'Oh we should've known you were with Don because you were with Pauly' and they say these names in the same sentence and I'm like, 'whoa!'" she shared on Sofia Franklyn's "Sophia With an F" podcast in July 2023.

She added, "That to me hurts the most because a guy that had a tanning bed in his home in Rhode Island that was chosen to be part of a show that was made to laugh at them is so beyond different than Donald Trump Jr."

According to Aubrey, the comparison of the Trump Organization's EVP and Pauly D was "horrific" and "one big equation of f------."

Months before Don Jr. and his then-fiancée Kimberly Guilfoyle broke up, Aubrey confessed she did not believe her ex was in a relationship with the former prosecutor.

"When he started dating Kimberly Garfield [Guilfoyle] and they were throwing their relationship everywhere after the wife finally left him and did whatever, then I was like, 'I don't believe this relationship for a hot second when I would watch her in interviews because that's just not his type,'" she said on Adam22's "No Jumper" podcast.

Aubrey added, "And I know what that man loves because he loved me so much he taught me how to love me differently."

In the book Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, Variety Editor-in-Chief Ramin Setoodeh cited The Celebrity Apprentice contestant Clay Aiken's comment about the affair, saying it "was not a well-kept secret" at the time.

Donald also confirmed in the book that he was aware of the story about his son.

"When I ask Trump about O'Day's affair with Don Jr., he takes a long pause. 'I had heard that, actually,' he says, blinking. 'No, I had heard that.' Did he know that O'Day had written a song about Don Jr.? 'I hadn't heard the song. But I had heard that,' Trump says, confirming once again that he's aware of the story about Don Jr. sleeping with one of the contestants on The Celebrity Apprentice," the excerpt read.

Don Jr. appeared in an interview with DJ Akademiks in 2024, during which he claimed Vanessa told him Kim Porter was "afraid" of Sean "Diddy" Combs while they were dating.

In response to the activist's statement, Aubrey told her followers on X that she was "in the CENTER of REALLY knowing ALL the information."

"I'm about to AUBREY ODAY the s--- out of everyone playing games right now," she added. "Y'all think this Kendrick [Lamar] & Drake s--- is cute.. just wait bc the EXpose hasn't even STARTED."

According to Aubrey, Don Jr. made her feel "the most beautiful" during their alleged affair.

"He made me feel the smartest and the most beautiful, but he loved my mind more than anything else, and that's what I love about me. The way that we loved was we loved the same," she told Us Weekly in an interview published in July.

Don Jr. got on Aubrey's nerves when the former The Apprentice boardroom judge called out Chelsea Clinton and referenced Bill Clinton's extramarital relationship with former White House intern Monica Lewinsky.

"You cheated on your wife as well.. don't mock your own reflection and call it someone else. Here's your seat," Aubrey added in the retweet on October 26.