The U.S. Ambassador to Greece and former prosecutor made a striking entrance at a high-profile event, igniting a wave of reactions and online speculation.
Kimberly Guilfoyle turned heads at the 2025 Wags to Riches Gala, held at the Mar-a-Lago Club on Saturday, March 22. The event, organized by Furry Friends—a Jupiter, Florida-based nonprofit dedicated to rescuing, rehabilitating, and re-homing homeless animals—brought together prominent figures for a charitable cause.
The television personality and former fiancée of Donald Trump Jr. made a striking entrance in a dramatic black gown, drawing attention both at the gala and across social media.
Guilfoyle, 56, made a glamorous entrance at the high-profile charity event in a floor-length black gown that highlighted her figure. The dress boasted a plunging neckline with sheer lace details, offering an alluring glimpse of skin.
Its voluminous skirt was adorned with black feathers, enhancing the gown’s dramatic flair. Guilfoyle completed the look with a bold statement necklace that accentuated the plunging neckline.
Her long brunette hair was styled in soft waves that cascaded over her shoulders, adding a touch of elegance. Guilfoyle exuded confidence as she mingled with other guests, appearing to enjoy the evening’s festivities.
A video shared by fashion designer Oscar Lopez on March 24 offered a glimpse into the luxurious event, showcasing the elegant décor, distinguished guests, and Guilfoyle herself. The clip captured her socializing and dancing, emphasizing the lively and celebratory atmosphere of the evening.
During the event, Guilfoyle was honored with the CIGO award for her contributions to animal rescue efforts. Investigative journalist Laura Loomer shared the moment on X, writing, “Congratulations to my friend @kimguilfoyle for receiving the CIGO award at the Furry Friends Animal Rescue Gala at Mar-a-Lago last night! Kimberly is a great defender and supporter of animals and does a lot to help and support local animal rescues in South Florida!”
A video included in Loomer’s post captured Guilfoyle accepting the award onstage and delivering a brief speech about her commitment to animal welfare.
The gala attracted several prominent figures, including actor Kelsey Grammer. Best known for his role in Frasier, Grammer sported a maroon-checkered tuxedo jacket over a crisp white button-down shirt, paired with blue trousers and matching sneakers. His appearance added to the evening’s star-studded allure.
Guilfoyle’s appearance at the gala quickly sparked online buzz, with many commenting on her striking new look. While some praised her glamorous style, others speculated about potential cosmetic procedures.
One person wrote, “She has a much softer look to her and she is gorgeous.” Another commented, “I will say she looks much healthier, thank God. Being with Jr was going to kill her [sic].”
One netizen remarked, “I’m not a fan of Kim’s, but she sure looks better since her separation from Jr. Is that even her?” Another added, “Best she’s ever looked.” A third person commented, “She got her face fixed!”
On Facebook, reactions were mixed, with some expressing skepticism about changes to her appearance. One person wrote, “Yea she doesn’t look that great. She’s had way too much plastic surgery [sic].”
Another added, “She was beautiful before she had all that work done.” A third comment read, “Too much Botox and injections [sic].”
Guilfoyle’s appearance at the gala came months after her split from Trump Jr., whom she had dated for several years. The two were first linked in 2018, after his divorce from Vanessa Trump.
On May 9, 2018, Page Six reported that a source had revealed, “Don Jr. and Kimberly are seeing each other, and are having a great time. While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly’s company.”
After dating for nearly three years, the couple got engaged on December 31, 2020—Trump Jr.’s birthday. However, they kept the news private until January 2022.
That month, Daily Mail confirmed their engagement, citing a source who revealed, “Don and Kim got engaged on New Year’s Eve 2020—which is Don’s birthday. They’ve been together for almost four years now and have been friends for 15 years.”
At the time, Guilfoyle expressed her excitement in a heartfelt Instagram post on January 1, 2022, writing, “Tonight was extra special celebrating @donaldjtrumpjr’s birthday. Don, you are strong, smart, courageous, funny, and the love of my life. I can’t wait to spend the rest of our lives together. Love you.”
She included photos from the celebration, featuring herself with Trump Jr. and Donald Trump, as well as a close-up of her engagement ring.
In late 2024, news broke that Guilfoyle and Trump Jr. had parted ways. Their breakup was confirmed by People on December 12, shortly after Trump Jr. was seen holding hands with Florida socialite Bettina Anderson.
At the time, a source cited by People stated, “It’s an amicable split. It’s not one that is going to blow up, at least at this point.”
Despite the breakup, Guilfoyle reportedly remains on good terms with the Trump family. The source further added, “The Trump family is still enamored with her. She’s very intelligent, very smart, very loyal. Even before she and Don were together, she was close with the family. She knew Donald before she knew Don Jr., and that connection is strong. So nothing has changed.”
However, the source also noted that Guilfoyle’s personality can be strong-willed, adding, “She’s not easy to deal with. She’s very direct, very matter of fact.”
Following her split from Trump Jr., Guilfoyle remained active in politics. On December 11, 2024, President Trump announced her appointment as the U.S. Ambassador to Greece in a post on Truth Social.
“Today, I am very pleased to announce the appointment of Kimberly Guilfoyle as the United States Ambassador to Greece. For many years, Kimberly has been a close friend and ally. Her extensive experience and leadership in law, media, and politics, along with her sharp intellect, make her supremely qualified to represent the United States and safeguard its interests abroad,” wrote the 47th U.S. President.
“Kimberly is perfectly suited to foster strong bilateral relations with Greece, advancing our interests on issues ranging from defense cooperation to trade and economic innovation. Congratulations Kimberly!” concluded the POTUS.
Guilfoyle also acknowledged her appointment in her Instagram bio, where she included the title, “Appointed by President Donald J. Trump as the U.S. Ambassador to Greece.”
Before stepping into the political arena, Guilfoyle was a well-known television host. She worked for Fox News for over a decade, serving as a co-host on The Five. However, in July 2018, Fox News confirmed her departure in a brief statement, saying, “Fox News has parted ways with Kimberly Guilfoyle.”
Her exit was abrupt, with no farewell appearance on air. Reports at the time suggested that her relationship with Trump Jr. had raised ethical concerns, particularly due to her frequent discussions about Donald Trump on the network.
Shortly after leaving Fox News, Guilfoyle joined Trump Jr. on the campaign trail for the 2018 midterm elections and later took on a role at America First Policies, a nonprofit supporting Trump’s agenda.
Guilfoyle’s appearance at the Wags to Riches Gala not only showcased her striking fashion choice but also highlighted her philanthropic efforts, political career, and continued public interest following her split from Donald Trump Jr.
As she takes on her new role as U.S. Ambassador to Greece, Guilfoyle’s influence in both social and political spheres continues to be a topic of discussion.
Meanwhile, her ex-fiancé Trump Jr. has moved on, sparking fresh speculation about his personal life. His new relationship with Bettina Anderson has attracted attention, with some insiders claiming she has a pattern of dating older, wealthy men.
Speculation about their relationship began in September 2024 after photos emerged of Trump Jr. and Bettina Anderson displaying affection at a restaurant near the Trump family’s Florida estate.
At the time, Trump Jr. was still publicly engaged to former Fox News host Kimberly Guilfoyle. However, a source alleged, “Don Jr. has been dating Bettina for about six months,” despite not commenting on his engagement to Guilfoyle, whom he proposed to in 2020.
The insider also claimed that the businessman “even took her on a trip to Alaska and introduced her around as his girlfriend when he was still very much with Kim.” Despite this, Guilfoyle reportedly ignored the situation, with the source adding, “For the most part, Kim has looked the other way because she loves the power and lifestyle.”
The former First Lady of San Francisco had previously expressed unwavering devotion to Trump Jr. on social media. In a Valentine’s Day tribute, she shared photos of the two together.
She described him as her best friend and greatest support, adding that she was falling more in love with him every day and looked forward to their future together.
Despite her public declarations of love, those close to Trump Jr. suggest their relationship had already run its course. According to a source, there was no expectation of a reconciliation, stating, “Don is ready to move on and has been doing so anyway. He just wants things to end as nicely as possible.”
Trump Jr. appeared to have fully moved on by December 2024, when he and Anderson were spotted holding hands during an evening stroll in Palm Beach, Florida. That night, the couple celebrated her birthday with a nearly two-hour dinner at the popular downtown restaurant Buccan.
A Palm Beach insider described Anderson as “a party girl, outgoing, and Don is smitten with her,” adding, “She is a big Republican, and wild.”
Another source offered a similar take, saying, “Bettina is smart, sexy, and savvy and knows it. She likes to have fun. Who knows what, if anything, will come from this.”
As Trump Jr.’s relationship with Anderson gained attention, those close to him reportedly voiced their disapproval. By late December 2024, sources claimed that members of his inner circle were pressuring him to distance himself from the 38-year-old Palm Beach socialite.
Their concerns centered around Anderson’s past political views, with some questioning whether she aligns with the Make America Great Again (MAGA) movement due to her previous support for the Black Lives Matter movement and strict COVID restrictions.
Others worry that her reputation for partying in Palm Beach does not fit the image expected of someone connected to the first family.
After making their relationship official, Anderson was set to accompany her boyfriend to his father’s inauguration on January 20, 2025, marking her first high-profile appearance by his side.
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Still, other insiders shared that the businessman and Anderson are not surprised by the gossip, recognizing that speculation and criticism are typical in their social circles.
Despite the ongoing discussions, Trump Jr. has not expressed any concerns about Anderson to his inner circle. However, those familiar with his political ties believe he is beginning to recognize how she is viewed within “MAGA” circles as more information about her background surfaces.
Concerns about Anderson’s relationship with Trump Jr. are not limited to politics, as longtime associates question her intentions. Speculation also arose that Anderson is using Trump Jr. as a “stepping stone” to connect with even “bigger fish,” including Elon Musk.
Since the 2024 election, Musk has been closely aligned with President Trump and was chosen to lead the DOGE agency, making him a central figure in the administration.
In Palm Beach, those familiar with Anderson’s background disclosed that she has a pattern of dating wealthy men who match her lifestyle, often receiving lavish gifts from her suitors.
Many in their social circle insist that protecting the Trump brand is a priority and worry that her growing presence around the family could bring unnecessary scrutiny. There are also claims that Kilo Content, a firm linked to Anderson, has been tipping off the media about her outings with Trump Jr. to raise her public profile.
Amid the skepticism surrounding Anderson, some have come to her defense, dismissing the criticism as baseless. Fashion designer Stacey Bendet, founder and CEO of Alice + Olivia, attributed the negative attention to women “fixating on competing” rather than supporting one another.
Bendet, who has been friends with Anderson for a decade, described her as “the kindest soul” with “the biggest heart,” adding that she is “witty and wise, hilariously funny, and an Ivy League grad.”
She noted that any negative claims about her friend are a reflection of societal pressures rather than reality. Bendet further emphasized, “Don adores her for good reasons!!” Over the years, Anderson has frequently been seen alongside Bendet at Alice + Olivia events, further highlighting their close friendship.
As Anderson receives support from those close to her, her relationship with Trump Jr. has reportedly become more serious. In January 2025, the two were spotted together in Washington, D.C., fueling speculation about their growing romance.