> At a Glance
> – Kimberly Guilfoyle publicly wished ex-fiancé Donald Trump Jr. “all the best” after his December 2025 engagement to Bettina Anderson
> – Guilfoyle and Trump Jr. ended their own four-year engagement in 2024
> – A source says Guilfoyle doubts the new relationship will last and believes Anderson is drawn to the Trump spotlight
> – Why it matters: The split and quick rebound spotlight the personal dynamics inside America’s most-watched political family
Kimberly Guilfoyle has ended months of silence on Donald Trump Jr.’s whirlwind engagement, telling the New York Times she’s “happy for Don.” The short comment, published Jan. 4, follows President Trump’s White House announcement that his eldest son is set to wed socialite Bettina Anderson.
The End of One Chapter
U.S. Ambassador to Greece Guilfoyle, 56, and Trump Jr., 48, got engaged on New Year’s Eve 2020 and confirmed it publicly in 2022. They quietly parted ways in 2024, leaving shared homes and belongings intertwined longer than expected.
- Closets still held Trump Jr.’s clothes and shoes at Guilfoyle’s residence months after the breakup, a source told News Of Los Angeles.
- The pair remain “great friends,” the insider added, but emotions lingered.
Doubts About the New Match
Behind Guilfoyle’s polite well-wishes, the source claims she worries Anderson sees the Trump name as a “ticket to prestige”:
- She questions whether the romance is “built to last.”
- She views Anderson as more interested in media attention than genuine partnership.
- Headlines about the new couple are “difficult” for her to digest.
Family Approval
President Trump reportedly had to warm up to his future daughter-in-law, initially put off by her eagerness to join the fold. Anderson ultimately adopted a lower profile, learning to “look beautiful, stand still and be subordinate,” the source said.
| Relationship | Status |
|---|---|
| Trump Jr. & Guilfoyle | Engaged 2020-2024, split quietly |
| Trump Jr. & Anderson | Engaged December 2025, announced by President Trump |
| Trump’s View | Approves of Anderson’s looks and “toned-down” approach |
Key Takeaways
- Guilfoyle publicly remains supportive but privately questions Trump Jr.’s new relationship.
- The Trump family’s acceptance of Anderson follows a pattern of valuing loyalty and low-drama optics.
- The engagement places another Trump wedding on the horizon as the family eyes 2026.
With nuptials ahead, the spotlight now shifts to whether Guilfoyle’s private doubts will play out in public view.
