Kimberly Guilfoyle And Don Jr.'s Split Isn't Keeping Them Apart (& It's Giving Bennifer)

dKimJunior? DonBerly? We can't quite decide on a couple's nickname for Donald Trump Jr. and Kimberly Guilfoyle, whose split was finally confirmed just before Christmas 2024. But it seems appropriate to decide on one now, since they're taking a page out of the Ben Affleck and Jennifer Garner divorce playbook, not to mention Affleck's more recent uncoupling from Jennifer Lopez. In both cases, the former couples made a conscious effort to stay civil for the sake of their children, even getting together for holidays and other family events. So it is with the incoming first son and the future U.S. ambassador to Greece.

On December 27, The Club at Admirals Cove, a ritzy country club in Jupiter, Florida, held its annual street fair, a one-day festival featuring rides, carnival games, and plenty of delicious food. Don Jr. posted a highlight of the night's festivities to his Instagram feed, captioning it: "Good times with the Smurfs!!!!" The businessman's video shows him on a pirate swing ride with 12-year-old Spencer and 10-year-old Chloe Trump, screaming just as loudly as the children. Don Jr.'s teens Kai, Donald III, and Tristan Trump, weren't pictured; either they were elsewhere at the time or chose to skip the outing altogether. 

But another significant person was present. Guilfoyle also notably posted shots of the fair to her Insta Stories, declaring it "THE BEST!!" Perhaps trying to silence the rumors of any hard feelings towards her ex-fiancé, the former Fox News host also liked Don Jr.'s post and even added the first comment too: "Such a fun night!" This set off some debate among followers as to whether it was appropriate for the two to be going out together as friends, with one commenter calling it "not normal." But at least one supporter sighed, "I miss seeing Kimberly with the Trump clan!!"

While plenty of MAGA fans saw the carnival night as a symbol of hope for the ongoing relationship between Kimberly Guilfoyle and Donald Trump Jr., one response to the eldest Trump son offered another clue entirely. Bettina Anderson, Don Jr.'s new girlfriend, also replied to his post with three white heart emojis, a mark of pure love. It's hard to say whether she was referring to her new man's demonstrable love for his children or her affection for all three of them, but the message was clear: She's an important part of the picture, too. Just days earlier, Anderson and Don Jr. made things official when they were photographed enjoying Christmas dinner at Mar-a-Lago. 

Considering the Trump men's history of publicly flinging mud at people they don't like, this display of unity between Don Jr. and the two women in his life is a positive sign. Just as Ben Affleck has managed to remain on good terms with both of his famous exes, it seems that the first son is doing his best to maintain a friendship with his former fiancée while still moving on with the model and socialite. 

This would certainly be in the best interest of his children — they've already lived through one divorce — not to mention Don Jr. himself. Guilfoyle is not only the co-owner of their house, but she's also a lawyer, journalist, and political commentator who could make things very uncomfortable for the public figure if he tries to humiliate her or soil her rep. Will the first son be able to ride this relationship roller-coaster to a smooth landing, or are there some curves up ahead that could throw Don Jr. off balance?