Kimberly Guilfoyle's Past Praise Of Don Jr.'s Fidelity Hasn't Aged Well

The Trumps don't have the best track record when it comes to fidelity, and Donald Trump Jr. is no exception. His first marriage ended in divorce because Don Jr. cheated on his wife, Vanessa Trump, with reality star and singer Aubrey O'Day. When he got engaged to Kimberly Guilfoyle, some assumed that Don Jr. was finally ready to settle down including, presumably, his new fiancée. At her birthday party in March 2024, Guilfoyle couldn't gush about Don Jr. enough, calling him "the greatest blessing in my life" before adding, "His loyalty and his fidelity and his enthusiasm for me is truly unparalleled to what I've experienced in this life," (via X, formerly known as Twitter). 

This wasn't the only time Guilfoyle sang her fiancé's praises either. When Don Jr's own birthday rolled around, she commemorated it on Instagram. "You are my best friend and my soulmate," the former Fox News host enthused. "Here's to us and our incredibly blessed life we share together. Looking forward to creating new memories and enjoying more adventures together." Unfortunately for Guilfoyle, her comments about Don Jr.'s unwavering loyalty to her didn't exactly age very well. Just a short while later, the internet was set ablaze when the Daily Mail published scandalous photographs showing Don Jr. looking very cozy with Bettina Anderson, a Palm Beach socialite. 

Eagle-eyed bystanders even told the outlet that they locked lips during their very public outing (there is no photographic evidence of this, however). "She seemed totally smitten with Don — and he with her," one eyewitness dished, while another added, "They were definitely on a date." A third bystander even detailed, "They weren't exactly making out, but the kisses were romantic, and you could tell they were intimate with each other." It seemed that, despite Guilfoyle's faith in her man, Don Jr. simply couldn't help himself, and while many waited for the couple to announce their inevitable breakup, it hasn't happened — yet.

After news of Donald Trump Jr. and Bettina Anderson's rather tactile public outing broke, Kimberly Guilfoyle tried to quell the affair rumors by staying mum, but insiders disclosed to the Daily Mail that she was caught completely unaware when the story dropped. "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," one source revealed, confirming that Guilfoyle had decided to bury her head in the sand. As a result, "What happens now is anyone's guess." To make matters worse, footage of Don Jr. and Anderson getting close at what appeared to be a small family gathering in Jupiter, Florida, was released to the public mere days after news of their initial outing broke. 

The businessman's ex-wife, Vanessa Trump, and his daughter Kai Trump were present as well and appeared to be very familiar with Anderson. Guilfoyle, on the other hand, was nowhere to be found. When Don Jr. took a trip to the Balkans in Europe not long after the rumors began circulating, though, the former Fox News host was traveling with him, and she made it known to the world. Taking to Instagram, Guilfoyle posted snaps of the two of them looking happy together, captioning the post: "Incredible trip to Belgrade, Serbia and Bucharest, Romania with @donaldjtrumpjr." Many saw this as a desperate attempt to bury the affair rumors, but alas, it has only increased the negative attention on the couple who, at the time of writing, are still engaged by all accounts.