We Bet Don Jr. & Bettina's Rare Display Of Affection Has Kimberly Guilfoyle Fuming

Taylor Swift didn't write "Mr. Perfectly Fine" about Donald Trump Jr., but we wouldn't be surprised if Kimberly Guilfoyle has been blasting that song since she and the first son broke up back in December. Because honestly, it seems like Don Jr. is doing amazingly well with his much younger girlfriend, Bettina Anderson, while Guilfoyle is begrudgingly picking up the pieces after her shattered relationship.

Don Jr. and Anderson aren't known for flaunting their PDA online, but they do occasionally remind the world that they're a couple. Recently, the socialite shared a three-photo collage to her Instagram Story that featured photos of her either walking with or sitting next to Don Jr. While not the most romantic photos — no kissing or holding each other — they still show a couple who are clearly smitten. Plus, two of the pics were in black and white, and, for whatever reason, that makes something look ten times more swoon-worthy.

Moreover, Don Jr. actually reposted Anderson's collage to his own Instagram Story. While this might seem like an "Okay, and?" moment, Anderson isn't featured on Don Jr.'s socials a ton, so it's noteworthy whenever she is. Guilfoyle is probably somewhere punching the air right now — feeling doubly upset over her ex since Don Jr. did include Anderson in a carousel celebrating President Donald Trump's birthday on June 14, 2025. Guilfoyle, unsurprisingly, was nowhere in sight on the father of five's Instagram.

While Kimberly Guilfoyle is maybe-kinda-still reeling from her breakup with Donald Trump Jr. after he ditched her for a younger woman, hopefully she is starting to realize just how awful her eventual marriage to her ex-fiance would have been. There are many painfully obvious signs that their happily ever after would have actually been miserable, including how Don Jr. seemingly doesn't care about being monogamous. Case in point, he was reportedly not broken up with the appointed U.S. ambassador to Greece when he was initially seen alongside Bettina Anderson. And an insider who spoke with People in December 2024 said he wasn't shy about calling Anderson "his girlfriend" before he and Guilfoyle ended things. He moved on super fast from Guilfoyle, which had to sting — and feel even worse when she realized it wasn't just a fling; Don Jr. and Anderson seem to be going strong.

But though he kicked her to the curb, Don Jr. still has memories with Guilfoyle on his Instagram. This includes a video of Guilfoyle dancing while the first son calls her "baby" in the background. Plus, he still has a 6-year anniversary post up, as well as a Valentine's Day selfie, both which feature "I love you" in the caption. For someone who rushed into a new relationship when the old one was barely over, it's interesting Don Jr. still has remnants of his former engagement on his social media. Seeing those photos and video still live on his page is probably tearing what's left of Guilfoyle's broken heart.