Kimberly Guilfoyle Dazzles In New Throwback Pics & We Can't Stop Thinking About One Thing

Kimberly Guilfoyle's besties are rallying around her in the wake of the former Fox News host's reported breakup with her fiancé, Donald Trump Jr. — but it's probably not having the effect they anticipated. Guilfoyle's psychotherapist buddy, Dr. Robi Ludwig, took to Instagram to congratulate her on her exciting new appointment as the U.S. Ambassador to Greece. But the accompanying photos only served to remind us of the humiliating reason Don Jr. reportedly ditched Guilfoyle for his alleged new mistress (besides cozying up to his famous father, of course). 

Ludwig shared a couple of snaps of Guilfoyle before her many alleged plastic surgeries, raunchy fashion sense, and heavy makeup took hold. Her eyes are clearly visible — a rarity for the former attorney these days. The woman in these pictures has soft eyes, a sweet smile, and a less artificial aura in general. In essence, she looks entirely different from the person who'll be working in the new Trump White House. On a somewhat sad note, the timeline of Guilfoyle's makeup style change between 2004 to 2024 lines up with her relationship with Don Jr.

By 2015, Guilfoyle still looked a lot like her natural self and seemed to view makeup the way most women do: As a tool to accentuate. But, by 2018, which just so happens to be the same year she began dating the president elect's son, everything changed. Their very public and increasingly messy breakup just goes to show that changing your physical appearance for a partner is never a good idea.

It definitely seemed a bit sus that Donald Trump chose to announce Kimberly Guilfoyle's nomination just one day after pictures of Donald Trump Jr. and his supposed new flame, socialite and model Bettina Anderson, began making the rounds on social media. And according to sources, this was not a mere coincidence; Donald Trump was really breaking up with Guilfoyle for Don Jr. "Bettina wants Kim out of the area. They are trying to send Kim abroad," an insider dished to People. Past reports also revealed that Don Jr. and his rumored new lady have been running in the same circles for quite a while. 

During the Republican National Convention, in July 2024, for example, Anderson was spotted sitting right behind the president elect's son and Guilfoyle. She was even seen chatting with Vanessa Trump afterwards too. This makes it seem highly probable that Don Jr. had already moved on and was only keeping up appearances to avoid affecting his father's election chances.

Whether or not these allegations are true, they certainly add a sour note to what should have been a high point in Guilfoyle's career. Rather than having a great reputation as a lawyer turned Fox News personality turned government official, she might simply be regarded as a spurned ex-lover who got an ambassadorship appointment as alimony for a seven-year relationship.