Aubrey O'Day Makes Boldest Claims Yet About Her Alleged Affair With Donald Trump Jr.

In one of the more left-field scandals to rock the Trump family, former Danity Kane singer Aubrey O'Day and Donald Trump Jr. reportedly had an affair after filming "Celebrity Apprentice" in 2011. As Page Six reported in March 2018, Trump Jr., a special adviser on the show at the time, pursued O'Day, a contestant on Season 5. Their romance reportedly got so intense that Don even told his then-wife of 13 years, Vanessa Trump, about the relationship and his plans to leave her for the singer. As Page Six sources claimed, O'Day was given the impression that Don Jr. and Vanessa's marriage "was already in the process of dissolving" before she entered the picture. 

In 2019, when asked by Variety about a scene on MTV's "Ex on the Beach," in which O'Day proclaimed that she and Don Jr. "were each other's soulmates," the reality star maintained her stance. "At the time, him and I were soulmates," O'Day said, adding, "I can only speak for myself, but I didn't break up a marriage and I wasn't involved in stealing anyone from their [spouse] and all that nonsense." Per Page Six, Vanessa filed for divorce from Don Jr. in 2018.

Now, the "Making the Band" alum is back with more insight into this past romance — and how her attitude about it has evolved.

Aubrey O'Day now feels guilty over alleged Donald Trump Jr. affair

On a December 14 episode of the "Call Her Daddy" podcast, Aubrey O'Day got candid about the nitty-gritty of her past alleged affair with Donald Trump Jr. According to O'Day, their connection was intellectually driven. "I was the last woman standing on ["Celebrity Apprentice"]. I was the youngest contestant ever ... He's a sapiosexual, he loves smart people," she shared. O'Day suggested that it helped that Trump Jr. could seemingly "be who he really is with me."

During their relationship, O'Day said she never felt like "the other woman," with Don Jr. giving her the impression that his and Vanessa Trump's then-marriage was more "a contract" than anything else. It was only when O'Day witnessed her best friend giving birth that she began empathizing with Don's ex-wife. "When I saw that, I felt to myself a little bit [of] accountability for Vanessa and I felt shame," O'Day admitted. The singer also confessed to being taken aback when Don broke things off. "He was the one that was pushing, he was the one that was calling me soulmate well before I even thought of him that way," she explained.

Although O'Day may be sympathetic toward Vanessa, she didn't hold back in a 2021 jab at Donald's current fiancee, Kimberly Guilfoyle. After a Twitter user called Don "a tool" who "whine[s] on Twitter all day long," O'Day fired back, "I'd rather whine on Twitter than f*** kimberly garfield any day." Vicious.