Kimberly Guilfoyle Clings To The Last Remnants Of Her Don Jr. Romance & It's Getting Sad

We are concerned, but not exactly surprised, by Kimberly Guilfoyle's recent behavior in relation to her former fiancé. Donald Trump Jr.'s eldest daughter, Kai Trump, turned 18 on May 12, 2025 and, in true Guilfoyle fashion, the newly-appointed U.S. ambassador to Greece commented on the celebratory post that the young golfer shared on Instagram. "17, you taught me a lot about life. 18, I hope you teach me a lot more," Kai captioned it. In response, Guilfoyle wrote, "What an exceptional baby girl turned into an amazing woman!" And, because it's the former Fox News host and staunch Trump loyalist, she included a whole slew of emojis, including the red heart and the American flag.

Sadly, Guilfoyle didn't stop at just Kai's Instagram post. She quickly hopped on over to Don Jr.'s page and left a comment on his birthday message for his daughter too while she was at it. "Most beautiful baby girl now, a woman," Guilfoyle gushed. The former prosecutor limited herself to only two emojis this time: A red heart and some praying hands. Both of the comments were top rated at the time of writing, most likely because fans kept upvoting them in between munching on popcorn, hoping some drama would unfold. 

But, it's worth noting that it's been months since Don Jr. finally confirmed that he and Guilfoyle had split up, following tons of speculation, and he's since moved on with socialite Bettina Anderson — someone who notably won over Kai faster than Guilfoyle ever did. Her comments feel like a last-ditch effort to stay relevant in the Trump family's mind.

Using Instagram to try and maintain her relationship with the Trump family isn't a new tactic for Kimberly Guilfoyle. Kai Trump's birthday posts are just the latest in a long string of attempts. On New Year's Eve in 2024, aka Donald Trump Jr.'s birthday, the mother of one went over-the-top celebrating him online. She shared a collage of photos to her Instagram Story that looked like pages from a digital scrapbook (they had split up by this point, just to be clear). Naturally, those Don Jr. birthday posts were a heartbreaking hint that Guilfoyle couldn't let go of the relationship.

A few days later, the former Fox News host used Eric Trump's birthday to desperately remind Don Jr. of happier times. Even worse, the pic she chose for her Instagram Story in that case was one that barely featured Eric at all, despite it being his birthday. Instead, Guilfoyle featured a zoomed-out snapshot of Eric, Don Jr., herself, and three of Don Jr.'s kids. Considering she was with him for years, it's unlikely the Trump staffer doesn't have at least one shot of her and Eric. But, she couldn't not-so-subtly remind Don Jr. how great they were together if she used it.

The whole situation is just sad, whichever way you look at it. Plainly speaking, the former prosecutor needs to cut the cord and move all the way on from Don Jr. and his family — which won't be easy, since Guilfoyle loves shamelessly sucking up to Donald Trump.