It was in 2018, just a few weeks after his divorce, that the freshly separated Donald Trump Jr. began dating former Victoria’s Secret lingerie model Kimberly Guilfoyle.

At that time, the new U.S. ambassador to Greece was 49 years old and an ardent supporter of Donald Trump, as reported by the German newspaper Bild.

Kimberly, apart from being a beauty, is also a law school graduate and a former television presenter in the U.S. According to international media, the two shared a passionate love affair.

I’m honored to accept President Trump’s nomination to serve as the next Ambassador to Greece and I look forward to earning the support of the U.S. Senate.

President Trump’s historic victory is bringing hope and optimism to the American people and to freedom-loving allies across… pic.twitter.com/ThyyDwOTNk

— Kimberly Guilfoyle (@kimguilfoyle) December 10, 2024

“I’m honored to accept President Trump’s nomination to serve as the next Ambassador to Greece and I look forward to earning the support of the U.S. Senate,” Guilfoyle wrote in a tweet.

For the American website Page Six, the brunette beauty and Donald Trump Jr. made their first public appearance as a couple at a party held in honor of the then-new U.S. ambassador to Germany, Richard Grenell.

The couple kept their distance during the event to avoid sparking gossip. However, their glances spoke volumes from across the room, and they left the party together.

Inside Kimberly Guilfoyle's rollercoaster relationship with the Trumps from 'prom king and queen of MAGA land' romance with Don Jr to their 'split' and her new envoy job in Greece https://t.co/hfdQQod5ji pic.twitter.com/fyUyrZkOTC

— Daily Mail Online (@MailOnline) December 11, 2024

At the time, Kimberly’s name was floated for a communications advisor role close to Donald Trump, with her telling the San Jose Mercury News: “I am a patriot, and it would be an honor to serve my country… I think it would be an exciting job, a challenge requiring someone determined, with deep expertise in communication.”

It is noted that Donald Trump Jr.’s ex-wife, Vanessa, is the mother of five children and a former model. She studied law and worked as an attorney but left her career to marry her sweetheart and dedicate herself to their family.

After the divorce, Donald Trump Jr. wasted no time. Following many romantic dates, he got engaged to Kimberly. However, their relationship didn’t last long.

Kimberly Guilfoyle: Degrees and Television Career

High-ranking U.S. sources explain that Trump’s decision to select the 55-year-old Guilfoyle over Greek-American Congressman Gus Bilirakis—whose name had been rumored for the position—was influenced by a desire to avoid jeopardizing control of the House of Representatives, a development that might hinder Trump’s policies.

Guilfoyle holds a bachelor’s degree from the School of Fine Arts at the University of California and a law degree from the University of San Francisco. Professionally, she crossed paths with Kamala Harris when both worked in the San Francisco District Attorney’s office.

However, “bad tongues” say their relationship was less than cordial, with Guilfoyle accusing the now Vice President of the U.S. of not supporting her professional advancement, while Harris reportedly stated: “I respect her, she’s a good attorney, and I want us to collaborate.”

During her four years at the District Attorney’s office, Guilfoyle received numerous accolades, including the distinction of “Prosecutor of the Month.”

In 2001, she made headlines when she successfully prosecuted two defendants whose dogs had fatally mauled a woman in San Francisco.

Around this time, she met her first husband, Gavin Newsom, who was elected mayor of San Francisco in 2003. The two even did a glamorous photoshoot for Harper’s Bazaar, which dubbed them “the new Kennedys.”

The FOX News Era

In 2006, alongside her divorce from Newsom, Guilfoyle made a definitive career shift from law to media.

Having gained experience in television productions like Both Sides on Court TV and Anderson Cooper 360° on CNN, Guilfoyle joined FOX News, initially for The Lineup before becoming co-host and eventually host of The Five.

In 2018, however, the new U.S. ambassador to Greece faced allegations of sexual harassment from a former assistant. U.S. media reported that the case was settled with a $4 million payout to the complainant and Guilfoyle’s dismissal.

The New York Times noted that the announcement of Guilfoyle’s appointment came just days after reports surfaced suggesting Donald Trump Jr. was romantically involved with influencer Bettina Anderson.