“Is That Even Her?” Kimberly Guilfoyle’s Look Sparks Buzz at Wags to Riches Gala

Kimberly Guilfoyle made waves at the 2025 Wags to Riches Gala, held at Mar-a-Lago on Saturday, March 22. Hosted by Furry Friends, a Jupiter, Florida-based nonprofit dedicated to rescuing and rehoming animals, the high-profile event drew notable guests—but it was Guilfoyle’s dramatic black gown and striking appearance that stole the show.

The former prosecutor, television personality, and ex-fiancée of Donald Trump Jr. turned heads both in person and online, igniting speculation and a flurry of reactions across social media.

Guilfoyle, 56, arrived at the high-profile charity event wearing a floor-length black gown that accentuated her figure. The dress featured a plunging neckline with sheer lace details, offering a glimpse of skin.

Her long brunette hair was styled in soft waves cascading over her shoulders. She looked confident as she mingled with other guests, appearing to enjoy the evening’s festivities.

One netizen asked, “I’m not a fan of Kim’s, but she sure looks better since her separation from Jr. Is that even her?” Another commented, “Best she’s ever looked.” “She got her face fixed!” someone else noted.

On Facebook, reactions were mixed, with some expressing skepticism about changes to her appearance. One person commented, “Yea she doesn’t look that great. She’s had way to much plastic surgery [sic].”

Another added, “She was beautiful before she had all that work done.” “Too much Botox and injections [sic],” wrote someone else.

Guilfoyle’s appearance at the gala came months after her split from Trump Jr., whom she dated for several years. The two were first linked in 2018, following 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 stated, “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 shared 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, noting, “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 includes the title, “Appointed by President Donald J. Trump as the U.S. Ambassador to Greece.”

Her exit was abrupt, with no farewell appearance on air. Reports at the time suggested that her relationship with Trump Jr. had created ethical concerns due to her frequent discussions about Donald Trump on the network.

Shortly after leaving Fox News, she 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 ongoing public interest following her split from Donald Trump Jr.

As she takes on her new role as U.S. Ambassador to Greece, her influence in both social and political spheres remains 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 drawn attention, with some insiders claiming she has a pattern of dating older, wealthy men.

Speculation about their relationship started in September 2024 after photos emerged of the two displaying affection at a restaurant near the Trump family’s Florida estate.

During that period, Trump Jr. remained 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 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.

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.

Another source offered a similar take, “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 are pressuring him to distance himself from the 38-year-old Palm Beach socialite.

Their concerns center 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.

Not everyone in Trump Jr.’s circle embraced the relationship. A source from the transition team voiced concerns, noting that while handling issues in Palm Beach was one thing, bringing them into the White House posed a different challenge.

Some close to Trump Jr. suspect Anderson has ulterior motives, believing she is leveraging the relationship to enhance her social status and influencer image. Others in their circle, however, aren’t surprised by the speculation, recognizing that scrutiny is par for the course in their world.

Despite the chatter, Trump Jr. has not voiced any concerns about Anderson to his inner circle. However, those familiar with his political ties believe he is starting to realize how she is perceived within “MAGA” circles as more details about her background emerge.

Skepticism about Anderson extends beyond politics. Longtime associates question her intentions, with some speculating she is using Trump Jr. as a stepping stone to more powerful connections, including Elon Musk. Since the 2024 election, Musk has been closely aligned with President Trump and was appointed to lead the DOGE agency, making him a central figure in the administration.

In Palm Beach, those familiar with Anderson’s past claim she has a pattern of dating wealthy men who match her lifestyle and often receives lavish gifts from suitors. Many in their social sphere insist that protecting the Trump brand is a priority and worry that her growing presence around the family could invite unwanted scrutiny. Additionally, some allege that Kilo Content, a firm linked to Anderson, has been tipping off the media about her outings with Trump Jr. to boost her public profile.

Amid the skepticism, Anderson has defenders. Fashion designer Stacey Bendet, founder and CEO of Alice + Olivia, dismissed the criticism as baseless, attributing it to women competing rather than supporting each other. A longtime friend of Anderson, Bendet 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 argued that the negativity surrounding Anderson is more reflective of societal pressures than reality. Bendet further emphasized, “Don adores her for good reasons!” Anderson’s close friendship with Bendet has been evident over the years, as she has frequently attended Alice + Olivia events.

As Anderson garners support, her relationship with Trump Jr. has reportedly grown more serious. In January 2025, they were spotted together in Washington, D.C., fueling speculation about their deepening romance.

A source revealed, “Don Jr. is essentially living with Bettina at her townhouse. His car is always there. Always.” By February 2025, insiders described their bond as strong, with many viewing Anderson as a positive presence in his life.

A third-generation Palm Beach native, Anderson has deep philanthropic roots. After attending Columbia University, she focused on mental health, conservation, and child literacy. Her family has a history of charitable work, with her father serving on prominent boards. She actively supports the Hope for Depression Research Foundation, Project Paradise, and the Literacy Coalition of Palm Beach County, where she volunteers weekly.

Her philanthropic efforts align with her professional endeavors. According to her LinkedIn profile, she is the founder and CEO of BAE Ventures LLC, a company that reflects her passion for style and environmental initiatives. She holds a Bachelor of Arts in Art History, Criticism, and Conservation from Columbia College at Columbia University, where she studied from 2005 to 2009.

Anderson has expressed deep pride in her involvement with the Project Paradise Film Fund, which aligns with her commitment to conservation. Her career philosophy emphasizes lifelong learning and purpose-driven work, aspiring to live “a significant life” defined by service, gratitude, and impact.

Guided by the belief that “to whom much is given, much is expected,” she views giving back as both a responsibility and a privilege. Yet, beyond her philanthropic work, Anderson’s striking appearance has also drawn attention. Admirers have praised her beauty, with one describing her as the “most beautiful woman on Earth,” while another simply wrote, “Wow.”

Not everyone has been as supportive. Some commenters have expressed nostalgia for Trump Jr.’s former fiancée, with remarks like “Bring back Kimberly!” and “Where’s Kimberly?” Despite mixed reactions, Anderson’s relationship with Trump Jr. continues to keep her in the public eye.

Before dating Anderson and being engaged to Kimberly Guilfoyle, Trump Jr. was married to Vanessa Trump. Their 12-year marriage ended in divorce, though the couple has remained committed to co-parenting their five children.

The socialite filed for an uncontested divorce in the Manhattan Supreme Court in 2018, finalizing what some described as a long-standing separation. According to reports, their relationship had been affected by his frequent travels and the backlash surrounding some of his social media posts. The pair had married in 2005 at Mar-a-Lago.

Anderson’s relationship with Trump Jr. has sparked both praise and criticism, with some admiring her background and others questioning her intentions. As their relationship moves forward, those in his circle remain split on whether she truly fits into his world.