Kimberly Guilfoyle once dreamt of being the daughter-in-law of the Trump family. The popular media personality was once engaged to the President’s son, Donald Trump Jr. Many expected the couple to marry in a lavish ceremony. Alas, Guilfoyle found herself unexpectedly single when Trump Jr. ended their long engagement in 2024 in favor of a much younger woman, a model, Bettina Anderson.
Following the breakup, Trump named Guilfoyle ambassador to Greece, which some viewed as a political olive branch. Therefore, she has maintained a dignified silence in public, avoiding any direct comments about her ex or the breakup.
However, according to a report from the Daily Mail, her private remarks have been far less diplomatic. An unnamed friend claimed Guilfoyle’s favorite line about her ex is that “he’s no prize.” While many see Don Jr. as a catch, his ex disagrees.
All’s fair in love and war. Wait until Kimberly Guilfoyle gets wind of this.
Junior dumped Kimberly for Bettina Anderson, who got dumped (or maybe never picked up) by Elon Musk, and then Anderson took up with Donald Trump, Jr. on the rebound. https://t.co/7UFBlhzrfN
— ┋𝔇𝔞𝔫𝔞’𝔰 𝔐𝔲𝔰𝔢┋ (@DanasMuse1) November 11, 2025
Even though Guilfoyle’s move to Greece may mark the beginning of a new chapter, the shadow of her past with her ex still seems to haunt her. Those close to the couple say the warning signs had been there for a while. Insiders say their age difference and lack of connection hinted the relationship was on borrowed time.
According to The List, one particular source of frustration for Kimberly Guilfoyle reportedly involves the waterfront mansion she still co-owns with Don Jr. Even though both he and Anderson have their own homes. Donald Trump Jr. continues to visit the property and even brings his new girlfriend with him.
“The last thing she wants is to see Bettina using something she owns.” Although Guilfoyle has vowed to move on, she remains uneasy about her personal belongings being used by her ex’s new partner, a source told the outlet.
However, despite all the drama, Guilfoyle has shown a professional attitude in public and attended several public events, including the inauguration, where Donald Trump Jr.’s new girlfriend, Bettina Anderson, was present. A source who was at the inauguration told PEOPLE the former couple was “civil” with “no negativity” throughout the event.
U.S. new Ambassador to Greece 🇬🇷
Kimberly Ann Guilfoyle
Once married to @GavinNewsom and once engaged to @DonaldJTrumpJr
She has seen both left and right. pic.twitter.com/ykl5JdK51m
— Dr. Farrukh Shamim ( Muhammad Malik) (@mmalikx7) November 5, 2025
As Kimberly Guilfoyle was appointed as the U.S. ambassador to Greece, Don Jr.’s ex took the bold step of moving out of the country for a fresh start. Reportedly, on November 4, she attended the official Ceremony of the Presentation of Credentials at the Presidential Palace in Athens to speak with Greek President Konstantinos Tasoulas.
As per sources, the MAGA women reportedly joked about finding a new husband with the President. She was married to Gavin Newsom, the California governor, from 2001 to 2006. They met in 1994 and had a brief romance before tying the knot. She then married Eric Villency and divorced a few years later.
In a July 2025 episode of The Shawn Ryan Show, the governor finally addressed that it was her entry into Fox News that made her delve deep into the sentiments of a Republican. ”
In some ways, if you go on Fox, you have to put a mask on — and your face grows into it,” he said. “Otherwise, you’re not going to last. But her face grew into it,” he added.
These remarks came right after the former progressive prosecutor was accused of going under the knife to achieve the MAGA effect ( big lips, dark brows and a lot of makeup).
U.S. new Ambassador to Greece 🇬🇷
Kimberly Ann Guilfoyle
Once married to @GavinNewsom and once engaged to @DonaldJTrumpJr
She has seen both left and right. pic.twitter.com/ykl5JdK51m
— Dr. Farrukh Shamim ( Muhammad Malik) (@mmalikx7) November 5, 2025
Furthermore, on the work front, Guilfoyle’s Instagram page has become a steady stream of praise for President Donald Trump, highlighting everything from his meetings with world leaders like Russian leader Vladimir Putin to her beautiful holiday moments, which show that she’s enjoying her singlehood to the fullest.
Yet, the constant support for the Republican Party could also mean Guilfoyle’s indirect message to her haters that she’s still a part of the “Trump World” and the “MAGA circle.”
Though the ambitious woman may no longer be part of the Trump family through marriage, she’s still very much part of its orbit, standing on her own terms and proving she doesn’t need a ring from an eligible politician ( who she once called her own) to remain relevant to the world.
