Don Jr. Repeats History In A Shady Way With Bettina Anderson Proposal
After splitting from his ex-fiancée Kimberly Guilfoyle in 2024, Donald Trump Jr. didn't take long to bounce back into relationship mode. The president's son was photographed kissing Palm Beach socialite Bettina Anderson near his father's Mar-a-Lago estate in September of that year. Rumors of their romance soon bubbled up, and before long their relationship was seemingly confirmed during the January 2025 inauguration events, which they attended together. Since then, the couple has been photographed side by side many times. Given their very public relationship, it was a shock to no one when, on December 15, 2025, it was announced that Trump Jr. and Anderson were engaged.
BREAKING: Donald Trump Jr. and Bettina Anderson are ENGAGED.
— Spencer Hakimian (@SpencerHakimian) December 16, 2025
Trump Jr.'s decision to pop the question near the holidays has sparked some conversation. He and Guilfoyle had announced their engagement in early January 2022, but Guilfoyle confirmed that Trump Jr. had actually proposed to her on New Year's Eve in 2020. The holiday-inspired proposals mark a trend in the businessman's relationships, an aptly fitting similarity given his overlapping dating timelines with Guilfoyle and Anderson. At the time that Trump Jr. was photographed kissing Anderson, neither he nor Guilfoyle had yet confirmed their separation or break up. Despite reports that he and his ex-fiancée still care deeply for each other, Guilfoyle knocked him down a peg in November 2025, allegedly saying that the Trump son is "no prize" (via Daily Mail).
Similarities in his relationships prove he's got a type
Both of Donald Trump Jr.'s recent fiancées share similarities, such as their pasts as models, but their relationships with POTUS' son also share some traits. For example, both Anderson and Guilfoyle were with Trump Jr. through his father's presidential campaigns. Guilfoyle stuck by her then-fiancé throughout the 2020 presidential run, and Anderson co-hosted a campaign fundraiser at Donald Trump's Mar-a-Lago estate in 2024.
The two women also seem to have spent a great amount of time in Florida with Trump Jr. He and Guilfoyle picked out a multi-million-dollar mansion to share post-engagement, and a source revealed in January 2025 that Anderson and Trump Jr. were essentially living together in the Sunshine State.
It's easy to tell that Trump Jr.'s recycled relationship trends have been around since his marriage to Vanessa Trump — whom he proposed to in November 2004. Also a model, Vanessa similarly experienced Trump Jr.'s serial monogamous behavior when, just a few months after their divorce, he was rumored to already be dating Guilfoyle.