Kimberly Guilfoyle Gets The Brunt Of Ex-Fiancé Don Jr.'s Quickie New Engagement

Bettina Anderson tried to soft launch her romance with Donald Trump Jr. in December 2024, and now, just one year later, the pair have announced their engagement. On December 15, Laura Loomer posted a video from a White House holiday celebration to X, formerly Twitter, where Donald Trump told the crowd that his son was tying the knot. Both Anderson and Don Jr. addressed their pending nuptials, with the formal model going out of her way to ingratiate herself with her future in-laws by praising Donald and Melania Trump for putting on the shindig. The news of the engagement to Anderson comes just a year after Don Jr. officially ended his very long engagement to Kimberly Guilfoyle.

BREAKING NEWS:

President Trump just announced at the White House that his son @DonaldJTrumpJr and his girlfriend Bettina Anderson are getting married! They just got engaged.

Congratulations to them both. pic.twitter.com/psb38nTGla

— Laura Loomer (@LauraLoomer) December 16, 2025

In the comment section of the video posted by Loomer, the engagement was overshadowed by people either mocking Guilfoyle or discussing why Don Jr. had broken up with Guilfoyle. "[Anderson]'s just fine being a trophy wife. Kimberly had her own career and own mind," one person wrote on X. At the time of their breakup in December 2024, it was rumored that Guilfoyle was too power-hungry for Don Jr., and that her hard-partying lifestyle became a point of contention for the couple.

"The Florida socialite did in a year what Kimberly Guilfoyle couldn't do in eight," another person replied on X. In fact, Don Jr.'s engagement to Anderson came so quickly that several users were unaware that he had even parted ways with Guilfoyle. "[W]hen did things end with Kimberly? Who is this woman?" one asked on X. "When she was shipped to Greece," another cheekily replied, referring to Guilfoyle's appointment as the U.S. Ambassador to Greece. Don Jr.'s new engagement may have seemed sudden, but he had been dating Anderson longer than most people realized.

Around the time of their split, news leaked that Donald Trump Jr.'s breakup with Kimberly Guilfoyle was messier than they let on. Besides being appointed to live in Greece by Donald Trump, there were other indicators that Don Jr. and Guilfoyle's protracted engagement was headed for disaster. Following their official split in December 2024, sources gave details about how inharmonious things had become between the former couple. "Kim is not happy about it. She didn't want it to end," one insider told Page Six at the time. "Don and Kimberly haven't been getting along over the past year. They get argumentative at Mar-a-Lago in front of people," a separate source told the outlet. 

The reason for their quarrelling was not difficult to pinpoint, as Don Jr. had been openly flaunting his relationship with Bettina Anderson by that time, even while still technically engaged to Guilfoyle. One source claimed that the two had been dating for six months before being seen in December. Of course, Don Jr. also cheated on his first wife. History rhymes, as they say.

A couple of months later, after the dust had started to settle around his breakup, Don Jr. brought Anderson with him to the Super Bowl along with his family. To make their relationship Instagram-official, he posted a carousel of the Trumps enjoying the big game from a suite, which included a couple of snaps of his new girlfriend posing with his kids. Similar to the reaction to his engagement to Anderson, many followers were surprised to see him with another woman. "U have switched your wife so quickly I missed something," one person wrote on Instagram, referring to his recent fiancée, poor ol' Guilfoyle.