Kimberly Guilfoyle's Filter Infatuation Can't Erase The Age Difference Between Her And Bettina

Kimberly Guilfoyle's Photoshop fails demonstrate that she's never heard the famous quote  "Insanity is doing the same thing over and over and expecting a different result." But, in light of her ex's high-profile new romance, the former Fox News host's attempts to enhance her looks are taking on an air of desperation. The most recent example of Guilfoyle's dodgy photo edits was the series of shots she posted from a fundraiser at President Donald Trump's Mar-a-Lago resort on the weekend of March 22, 2025. On the plus side, the event raised money for a local animal rescue. On the minus side... well, where to begin? 

The newly-minted U.S. ambassador to Greece donned a gown with a low-cut lace bodice and a feathered skirt, making her look more like a Wild West saloon girl than someone with a plush government job. But more startling still was the heavy filter on the pics. Donald Trump Jr.'s former fiancée may have been trying to highlight the so-called "Mar-a-Lago face" trend she and many other conservative women have embraced recently, but she was almost unrecognizable. A pic Guilfoyle shared of herself with her son, Ronan Villency, even made her look more like his prom date than his mother (cue the shuddering).

@kimberlyguilfoyle/Instagram

It's hard not to wonder whether she would be trying this hard if the circumstances of her breakup from the president's eldest son had been different. In a crushing end to their years-long engagement, Don Jr. humiliatingly ditched Guilfoyle for his mistress, socialite Bettina Anderson, who will be 39 later this year while Guilfoyle turned 56 earlier this month. Despite all the trendy embrace-your-age messages women get, it still has to be a massive ego blow to see your ex with a much younger woman.

Donald Trump Jr. took his relationship with Bettina Anderson to the next level just a few months after they went public. He took Anderson on a fishing excursion with three of his five children, making it clear that things are getting serious between them. This must have hit a raw nerve with Kimberly Guilfoyle, who was also introduced as Don Jr.'s flame on social media via a photo of them out on the water with their catch of the day. Yet rather than going off and catching a marlin or two of her own, the former Fox News host continues to show off her glamour shots with every wrinkle and blemish digitally wiped away. 

Alas, no amount of alteration can make a Gen Xer like Guilfoyle resemble Anderson and her millennial peers. It also sends a toxic message that beauty means never showing even a hint of ageing. We'll concede that Lara Trump has dethroned Guilfoyle in the most edited selfie category of sins. Eric Trump's wife recently took to Instagram to plug a patriotic necklace, but her eerily super-filtered face took attention away from the bauble. 

Still, the new U.S. ambassador to Greece comes in a very close second (which is really nothing to brag about). Guilfoyle appeared at the White House on March 24 for the upcoming Greek Independence Day, where she spoke of the "honor and privilege of a lifetime to serve this country" in her new role (via Instagram). We're hoping the staunch Trump loyalist will have less time for digital airbrushing once she's Mediterranean-bound.