One thing Donald Trump and his son Donald Trump Jr. have in common besides their name and family ties? They both have a hard time staying loyal. Towards the end of his four-year engagement to Kimberly Guilfoyle, Don Jr. sparked rumors of relationship overlap when he was spotted on a cozy dinner date with his now-girlfriend, Bettina Anderson. He may not have technically cheated, though, as it turned out he and Guilfoyle had already separated, but given Don Jr.’s track record, it’s hard not to raise an eyebrow. During his marriage to Vanessa Trump, Don Jr. allegedly had an affair with singer Aubrey O’Day while Vanessa was pregnant with their son, Tristan. The story goes that Junior fell for his mistress while he was acting as an adviser on NBC’s “The Celebrity Apprentice” hosted by his father, where O’Day was a contestant.

Whereas Don Jr. never publicly acknowledged the tryst, O’Day is the exact opposite. She’s repeatedly referred to the first son as her “soulmate” and has been very open about their past. “We both thought we were each other’s soulmates. It’s something we spoke about often,” she told People. “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.”

She also didn’t hold back when it came to discussing the more intimate details of their romance, revealing that she and Don had sex for the first time in the bathroom of a gay club she was hosting. “That otherwise would be one of the most humiliating stories ever, but it was very him and I,” the former Danity Kane member gushed on Michael Cohen’s “Mea Culpa” podcast. Unfortunately for Don (and also Vanessa), his Bratz doll-looking ex-mistress refuses to stop bringing up their steamy past.

Was it love or just lust? If you ask Aubrey O’Day, what she and Donald Trump Jr. had wasn’t just a casual romance. “Don Jr. made me feel the most beautiful,” the former “Celebrity Apprentice” star reflected in a July 2025 interview with Us Weekly. “He made me feel the smartest and the most beautiful.” She continued, “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.”

So serious was their relationship, in fact, that O’Day says Don Jr. was willing to turn his back on his wife and kids so he can be with her. In the end, Don left her hanging and chose his family over the chance to start a new life with her. A source from People claimed that Vanessa Trump discovered her husband’s affair through text messages O’Day had sent Junior while he was in the shower. (Real soap opera stuff). However, she didn’t file for divorce until March 2018, after which Vanessa moved on with legendary golfer (and also serial cheater) Tiger Woods.

“My response was always, ‘I never cheated on anyone,'” O’Day told Vanity Fair in July 2023. But after a while, she realized she may not have been entirely blameless. “I’m an honest person,” she explained when asked why she continues to speak openly about her past with Don Jr. “I’m just saying what my truth is… and I don’t want to hide it in order to please other people.”