One factor Donald Trump and his son Donald Trump Jr. have in frequent moreover their identify and household ties? They each have a tough time staying loyal. In direction of the tip of his four-year engagement to Kimberly Guilfoyle, Don Jr. sparked rumors of relationship overlap when he was noticed on a comfy dinner date along with his now-girlfriend, Bettina Anderson. He could not have technically cheated, although, because it turned out he and Guilfoyle had already separated, however given Don Jr.’s monitor report, it is laborious to not elevate an eyebrow. Throughout his marriage to Vanessa Trump, Don Jr. allegedly had an affair with singer Aubrey O’Day whereas Vanessa was pregnant with their son, Tristan. The story goes that Junior fell for his mistress whereas he was performing as an adviser on NBC’s “The Superstar Apprentice” hosted by his father, the place O’Day was a contestant.

Whereas Don Jr. by no means publicly acknowledged the tryst, O’Day is the precise reverse. She’s repeatedly referred to the primary son as her “soulmate” and has been very open about their previous. “We each thought we have been one another’s soulmates. It is one thing we spoke about typically,” she advised Individuals. “A soulmate is somebody you spend a time period, second, of life with that you simply’re related as one. I had that with Don.”

She additionally did not maintain again when it got here to discussing the extra intimate particulars of their romance, revealing that she and Don had intercourse for the primary time within the lavatory of a homosexual membership she was internet hosting. “That in any other case could be one of the humiliating tales ever, but it surely was very him and I,” the previous Danity Kane member gushed on Michael Cohen’s “Mea Culpa” podcast. Sadly for Don (and in addition Vanessa), his Bratz doll-looking ex-mistress refuses to cease mentioning their steamy previous.

Was it love or simply lust? For those who ask Aubrey O’Day, what she and Donald Trump Jr. had wasn’t only a informal romance. “Don Jr. made me really feel probably the most lovely,” the previous “Superstar Apprentice” star mirrored in a July 2025 interview with Us Weekly. “He made me really feel the neatest and probably the most lovely.” She continued, “However he cherished my thoughts greater than anything, and that is what I like about me. The best way that we cherished was we cherished the identical.”

So critical was their relationship, actually, that O’Day says Don Jr. was prepared to show his again on his spouse and children so he could be together with her. In the long run, Don left her hanging and selected his household over the prospect to start out a brand new life together with her. A supply from Individuals claimed that Vanessa Trump found her husband’s affair by way of textual content messages O’Day had despatched Junior whereas he was within the bathe. (Actual cleaning soap opera stuff). Nonetheless, she did not file for divorce till March 2018, after which Vanessa moved on with legendary golfer (and in addition serial cheater) Tiger Woods.

“My response was all the time, ‘I by no means cheated on anybody,'” O’Day advised Vainness Truthful in July 2023. However after some time, she realized she could not have been fully innocent. “I am an trustworthy particular person,” she defined when requested why she continues to talk brazenly about her previous with Don Jr. “I am simply saying what my fact is… and I do not wish to cover it in an effort to please different folks.”