Kimberly Guilfoyle Accidentally Confirms She's Living In La-La Land After Don Jr. Affair Scandal

While Donald Trump Jr. seems to be publicly flaunting his relationship with his alleged mistress, his fiancee, Kimberly Guilfoyle, seems to have her mind in the Mediterranean.

Don Jr. and Guilfoyle got engaged back in 2020, but all signs point to the wedding never happening. While the couple hasn't publicly called off their engagement, several sources say they're kaput. And they really couldn't be further apart at the moment. Not only did the Daily Mail publish photos of the president-elect's eldest son enjoying a night out in Palm Beach with model and socialite Bettina Anderson on December 10, 2024, but Anderson herself shared an Instagram Story of a birthday card one could assume was from Don Jr. The big clue? Don Jr. is slyly tagged in tiny text in the top corner of the story.

The card is definitely not one you'd expect to be exchanged between people who are just good friends. It is printed with the word "loves" and bears the message, "Many have said you are aging out, but I think you are perfect. Happy birthday!" So, what's Guilfoyle been up to during all this?

Essentially, Kimberly Guilfoyle has been doggedly avoiding addressing the elephant in the room for months. Rumors of Donald Trump Jr.'s affair with Anderson have been swirling since at least September, and Guilfoyle has been deflecting for the entire time, instead sticking to campaign-related social media posts and sharing uncomfortably stiff photos of herself with her fiance at various events.

The newest wrinkle is that Guilfoyle is celebrating what many are seeing as the surest sign that she's out of the family. President-elect Donald Trump announced on December 10 that he was appointing Guilfoyle as his ambassador to Greece, writing on Truth Social, "For many years, Kimberly has been a close friend and ally. Her extensive experience and leadership in law, media, and politics along with her sharp intellect make her supremely qualified to represent the United States, and safeguard its interests abroad."

Guilfoyle responded to the appointment, which places her a little over 5,000 miles away from her fiance, with immense gratitude, writing on X, formerly Twitter, "As ambassador, I look forward to delivering on the Trump agenda, supporting our Greek allies, and ushering in a new era of peace and prosperity." Don Jr. also commented on the appointment, posting to X, "I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First."

In what might be one of the greatest cases of misreading social media in political history, Kimberly Guilfoyle even posted on her Instagram story that "Greece" was the number one trending topic on X, writing, "Number one trending on X! Let's go!"

But people weren't posting to congratulate her. Well, some were, but most were reading the tea leaves and coming to the conclusion that Guilfoyle is being sent as far away from Donald Trump Jr. and his new squeeze as possible. One person commented on Guilfoyle's own X post, referring to her and Don Jr.'s home in Jupiter, Florida, "That's one way of getting you out of Jupiter so Jr. has space with his new girlfriend." Another decided to get very real with Guilfoyle, writing, "They are disposing of you Kim." And another commenter seemed to be begging Guilfoyle to share her honest thoughts on the situation, tweeting, "Spill the tea, lady!!!! They did you dirty."

Given Guilfoyle's public reaction to everything that's going on, it's honestly hard to know whether she's clear-eyed about the circumstances or deeply in denial. Notably, Don Jr. divorced his wife of 13 years, Vanessa Trump, in 2018. That was the same year Guilfoyle and Don Jr. started dating, making their relationship official as Don Jr. and Vanessa finalized their divorce. Guilfoyle has been married twice, to California Gov. Gavin Newsom and businessman Eric Villency.