In Trumpworld, a single holiday photo can confirm a breakup and lock in an engagement without so much as a caption to say much of anything at all. Well, at least that’s what happened after Don Jr. and his fiancée, Bettina Anderson (a Palm Beach socialite), appeared together at the Trump Tower Christmas party in New York on December 13.
The couple shared some Christmas tree-side snaps to their Instagram Stories. They disappeared within 24 hours, but screenshots are forever, and by the time the images reached X (formerly Twitter), the relationship became the real thing.
For anyone keeping score, just two weeks before Christmas 2024, Don Jr. confirmed his split from Kimberly Guilfoyle after six years of engagement. Tabloids soon showed him stepping out with Anderson in Palm Beach. A year later, by Christmas 2025, they were at weekend getaways and spending family time with Don’s five kids. Plus, of course, there were the hangouts with Ivanka Trump.
Now comes a public appearance at one of the significant events on the Trump calendar.
Don Jr & his girlfriend Bettina at the Trump Tower Christmas party ❤️🎄 pic.twitter.com/q8rTzhf12n
— Keeping Up With The Trumps (@KUWTTRUMPS) December 14, 2025
What made the confirmation worse was who wasn’t in the frame, aka Guilfoyle, who was sworn in as U.S. ambassador to Greece earlier this year. Of course, social media noticed. One Trump supporter reacted: “Where is Kimberly??” Others offered her well-wishes in Athens, “Still can’t get used to him without Kim. I hope she finds some really attractive Greek husband.”
That mention speaks to the way Don Jr. and Guilfoyle’s relationship ended. They were joined at the hip and always at Republican conventions. Then suddenly there’s a new woman with no formal handoff. So yes, while the Trump Tower photo introduced Anderson to the broader MAGA audience, it surely closed the door on Guilfoyle.
Supporters on X called Anderson an “upgrade,” as they praised her natural look. Several commenters said she looked different from what critics often call the “Mar-a-Lago face.” One user approved: “Very pretty. I hope [Anderson] doesn’t go with the big lips and all the dark makeup.”
She went from this to this …
Kimberly Guilfoyle typically seems to look worse the closer you get. pic.twitter.com/XQucqvjbdY
— Chetter 📢🗽⚖💙 Beacon for Democracy (@ChetterHub) December 13, 2025
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Skeptics, on the other hand, weren’t convinced of this romance. “He’ll have a new one for the Easter festivities,” one scoffed. Others are reviving nostalgia for Don Jr.’s first marriage. A post even asked him to reconcile with Vanessa Trump, as it calls her “the most stunning and classiest mom” and prays the couple would reunite “for the sake of your kids.”
That ship has very much sailed, though. Vanessa Trump divorced Don Jr. in 2018 and is now reportedly in a relationship with golf legend Tiger Woods. Guilfoyle, too, has landed on her feet as she was sworn in as ambassador to Greece in September and is now dispatched to Athens.
President Donald Trump himself confirmed his son’s latest engagement at a White House holiday party this week, and a spokesperson confirmed as well. Do you think Don Jr.’s third engagement can make it to a wedding?
