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Guilfoyle Reportedly Skeptical of Don Jr.’s Engagement After White House Announcement

Guilfoyle, now U.S. ambassador to Greece, has not commented publicly on the relationship.

Overview

  • President Trump revealed Donald Trump Jr.’s engagement to Bettina Anderson during a White House Christmas reception, where the couple briefly addressed guests.
  • Insiders cited by People say Kimberly Guilfoyle doubts the match will last and believes Anderson is drawn to Trump-family prestige, a characterization she has not confirmed.
  • Guilfoyle serves as U.S. ambassador to Greece following nomination by the president and Senate confirmation, with some sources alleging the posting was meant to send her abroad.
  • Trump Jr. and Guilfoyle dated from 2018 to 2024, and reports say he began seeing Anderson in spring 2024 before the couple appeared together at high-profile events throughout 2025.
  • Forbes reported that Anderson’s engagement ring is an eight-carat emerald-cut diamond designed by Dallas jeweler Sue Gragg.