One person with first-hand knowledge of the Trump family is having none of Jesse Watters’ fantasy that Sydney Sweeney and Barron Trump will get married.
On Monday night, Aubrey O’Day took to X to comment on the Fox host’s Sweeney prediction, which came after several MAGA sphere members expressed their support for the embattled actress.
until he falls in love with his mistress. They always want more than who they married. https://t.co/AVHQeCDIZd
— Aubrey O’Day (@AubreyODay) August 5, 2025
The former Danity Kane singer shared a post quoting Watters’ prediction that Sweeney and Trump would get together and wrote, “until he falls in love with his mistress. They always want more than who they married.”
Her tongue-in-cheek call-out harkens back to her relationship with Trump Jr., which O’Day says started while she was a contestant on his father’s show, The Celebrity Apprentice.
She claims that the tryst lasted from late 2011 to early 2012, when Trump Jr.’s then-wife Vanessa discovered emails between the two.
“He made me feel the smartest and the most beautiful,” O’Day said about Trump Jr. last month in an interview with Us Weekly.
She has also said that the two first had sex in a gay nightclub where she was performing, a setting she claimed Trump Jr. was “very comfortable” in.
.@AubreyODay describes her past relationship with Don Jr. and his stunning hypocrisy. https://t.co/ng0I7QG19M pic.twitter.com/uSVU325yPR
— MeidasTouch (@MeidasTouch) July 6, 2023
Trump Jr. has never commented on the alleged affair, although it may have ended his marriage.
Vanessa Trump filed for divorce in 2018, shortly after Page Six exposed the affair to the public and the Wall Street Journal reported that Trump family fixer Michael Cohen quashed a potential story about it back in 2013.
Cohen made a habit of cleaning up after the Trump family’s messes at that time.
The hush-money payments that he arranged to adult actress Stormy Daniels, who claimed she had an affair with Donald Trump while Melania Trump was pregnant with Barron, landed him in federal prison for three years and later led to Donald Trump’s criminal conviction in New York state court.
Trump Jr. has at times attracted attention for bawdy commentary about women reminiscent of his father’s.
Don Jr.: “Can you believe the hell I’m going through? I’m at the Playboy Mansion with a pregnant wife! It doesn’t get worse than that, does it?” https://t.co/wXHjkrMigQ
— HuffPost (@HuffPost) April 5, 2018
In 2007, when his wife was pregnant, he complained in an interview that it was “hell” to visit the Playboy Mansion with a pregnant wife.
“It doesn’t get worse than that, does it?”
The post Don Jr.’s Ex-Mistress Weighs In on Fox’s Weird Sydney Sweeney-Barron Trump Fantasy appeared first on The Daily Beast.
