Don Jr.'s Fiancée Looks Painfully Tuned Up At 2026 SOTU (& It's Giving Guilfoyle)

Donald Trump Jr. and Bettina Anderson's relationship unofficially entered the spotlight in August 2024, at a time when Don Jr. and Kimberly Guilfoyle hadn't even made their breakup public. Anderson and Trump were seen publicly holding hands in December, and they went Instagram official by February 2025, with Don Jr. posting pictures of the couple at the Super Bowl. The next month, Anderson attended Donald Trump's congressional address, and almost a year later, she joined the Trump family for the president's State of the Union.

Although Anderson's outfit for both events was relatively similar (a black pantsuit at one, a black pinstripe pantsuit at the other), her face looked noticeably different. Anderson appeared to have Mar-a-Lago face in the making in 2025, and the transformation seemed complete by the State of the Union. Not only did Anderson look nearly unrecognizable when compared to her old modeling pics, but she seemed to have developed facial features that are weirdly reminiscent of Guilfoyle.

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Guilfoyle has long been the poster woman for Mar-a-Lago face, but Anderson's quickly catching up. Compared to how she looked a year ago, her cheekbones are more prominent, and her cheeks are noticeably hollowed out. Anderson's lips are also quite a bit plumper, making it look like she's constantly puckering up. 

Guilfoyle's own prominent pout has long been criticized and compared to a fish. However, trends like the "trout pout" are cyclical, and enhanced lips like Anderson's and Guilfoyle's have been alternatively scorned and celebrated. Bizarrely, some modern treatments even utilize trout DNA, putting a new spin on the fish-related digs.

At first glance, Bettina Anderson may seem stuck following in Kimberly Guilfoyle's footsteps, from her facial features to her relationship with Donald Trump Jr. However, Anderson and Don Jr. had a fairly whirlwind engagement in comparison. He recapped the aftermath of his proposal at a White House holiday party in December 2025, and the recording hit social media that night.

In contrast, when Don Jr. and Guilfoyle got engaged in 2020, the former couple didn't divulge the relationship milestone until early 2022, even when there were clear openings to do so during media appearances. Of course, that engagement went nowhere. While Don Jr. and Anderson's willingness to discuss their commitment seems to indicate a stronger foundation, Anderson still has some possible pitfalls to avoid. Donald Trump gave Anderson a suspicious response after the engagement news, saying, "Good luck" (via X, formerly Twitter). Trump's comment could be a warning to Anderson to avoid ending up with a broken engagement like Guilfoyle.

Luckily, Anderson seems to have already diverged from Guilfoyle in crucial ways. Before their engagement, Anderson went on a tropical getaway with Ivanka Trump's family, demonstrating a closeness that Guilfoyle struggled to forge. Even though that "good luck" of Trump's was slightly ominous, Anderson has reportedly made inroads with her future father-in-law. "She has toned down, realizing that she has to look beautiful, stand still, and be subordinate to anything the Trumps do," one insider divulged to People. "She has managed to mellow out enough to be accepted." Between that and her cosmetic procedures, she should be just fine.