Don Jr. Accidentally Confirms Kimberly Guilfoyle Isn't The Only Woman On His Mind

Open mouth, insert foot. In case you had any doubts, Donald Trump Jr. has once again proven that he is a chip off the old block, with a wandering eye to boot. "Biological & objectively attractive women are allowed to win beauty pageants again. WE ARE SO BACK!!!" the purportedly still engaged businessman tweeted on November 18 in celebration of Miss Denmark, Victoria Kjær Theilvig's victory at the 2024 Miss Universe pageant. Think blond, tan, big ... er, personality. 

The tweet was no doubt a thinly veiled swipe at the Miss Universe organization's 2012 decision to lift the ban on transgender contestants being allowed to compete — mind you, a decision that took place while Don Jr.'s famous father, Donald J. Trump, was still the owner of said organization. Alas, that's neither here nor there. Perhaps the one who should be most offended by his social media post is his long-time fiancee, Kimberly Guilfoyle, as the only thing the tweet really did was confirm that she's not the only woman on his mind. On top of that, many past winners have been dark-eyed and brunette like Guilfoyle. However, the victor Don Jr. was excited about celebrating had light eyes and blond hair — traits possessed by one of his rumored exes.

Unfortunately, now would not be the time to feign shock and outrage over the possibility that Donald Trump Jr. might be guilty of thinking about other women. As the old saying goes, tigers don't change their stripes. (Cue the biggest romance rumors to ever surround Don Jr.)

As you may recall, it's been widely speculated that Don Jr. had an affair with former Danity Kane singer Aubrey O'Day whilst still married to his wife and the mother of his five children, Vanessa Haydon — who, like O'Day, is blond. Reportedly, the affair resulted in a blowup of epic proportions between Vanessa and O'Day. Years later, however, O'Day continued to profess her love for Don Jr., even telling Page Six he was her "soulmate." Alas, that's just the tip of the iceberg. Don Jr. made headlines back in September when he was spotted having an intimate lunch with Bettina Anderson, as evidenced in photos obtained by the Daily Mail. Eyewitnesses even claimed that they saw Don Jr. kissing Anderson, a Palm Beach socialite who looks like a pageant queen. Ruh roh. While neither Don Jr. nor Kimberly Guilfoyle have commented on the scandal, one source later told the Daily Mail that "Kimberly either didn't know about Bettina — or didn't want to know. Did she hear whispers that Don Jr. was fooling around with someone else? Probably." Guilfoyle, blink twice if you need help.