Kimberly Guilfoyle is recognized for her connections with politicians like Gavin Newson, an extensive career both as a lawyer and TV personality, a brief period as a lingerie and fashion model, as well as her involvement in the 2017 scandal at Fox News.

Guilfoyle has been deeply intertwined with the Trump campaign and family since 2016 – becoming the fiancé of Donald Trump Jr. in 2020.

But years later, the stability of that relationship is being called into question. 

Don Jr. was caught locking lips with a Republican Palm Beach socialite, DailyMail.com revealed on Sunday. 

The former president’s son was spotted out to eat with ‘it girl’ Bettina Anderson, 37, during an intimate brunch date last month.

In exclusive pictures obtained by DailyMail.com, Don Jr. was seen meeting with the model, influencer, and philanthropist at The Honor Bar, situated within Palm Beach’s Royal Poinciana Plaza shopping center on August 17.

Witnesses said it was clear this was a date, with one revealing Anderson was seen reaching over to kiss Don Jr.’s three times.

But his fiancé Guilfoyle was nowhere in sight. 

Kimberly Guilfoyle is a prolific lawyer who received her Juris Doctor from the University of San Francisco School of Law in 1994. 

She paid her way through law school by holding up three jobs: an intern at a district attorney’s office, a clothing store, and as a lingerie and fashion model in the San Francisco and Sacramento area, Guilfoyle told Cosmopolitan. 

The model campaigns were featured in local department stores such as Macy’s and she modeled Victoria Secret lingerie for a bridal magazine.

She also had an interest in politics. 

In 1995, she worked on the reelection campaign for district attorney Arlo Smith. Guilfoyle was frequented political fundraisers organized by oil billionaire Gordon Getty – dating his son William. 

After their break-up, Guilfoyle moved up the political ladder after she began dating politician Gavin Newsom who was the San Francisco city supervisor at the time. 

 She married him in 2004 before divorcing in 2006 after it was revealed in 2008 that Newsom had an affair with Ruby Rippey-Tourk. the wife of his then-campaign manager and former deputy of staff, Alex Tourk.

While working as a prosecutor in San Francisco, Guilfoyle butted heads with Kamala Harris who was working as a former Alameda County prosecutor who supervised the office’s Career Criminal Unit.

Guilfoyle said: ‘She called me and said basically that she was on the hiring committee and in charge of the budget for the D.A.’s office, and that I should have gone through her if I wanted to return to the D.A.’s office — and that there was no money to hire me.’

Harris has recalled that conversation differently saying she never told Guilfoyle there was no job or discouraged her from joining the office.

Guilfoyle broke into the world of broadcast media in 2004 when she worked as a legal analyst on Anderson Cooper 360 and joined Fox News in February 2006 as the host of The Lineup – later joining The Five as a co-host in 2011.  

She would secure a long-term contract with Fox in mid-2017, before abruptly leaving in July of 2018 after a year-long investigation of sexual harassment against her left network officials giving Guilfoyle the option of termination or resignation. 

Fox News would agree to an out-of-court settlement against Guilfoyle’s accuser – who was an assistant – that was at least $4 million, the New Yorker reported.

This didn’t leave Guilfoyle without a job or feeling the repercussions of the #MeToo movement that was in full swing. 

She had already been considered for the position of press secretary for former President Donald Trump in 2016. So the move to work for pro-Donald Trump super PAC was a no-brainer. 

She had also been dating Donald Trump Jr. since mid-2018, confirmed by Vanessa Trump who had filed for divorce from Donald Trump Jr. three months earlier. 

The couple got engaged on December 31, 2020 but it wasn’t made public until January 2022. 

Guilfoyle has been criticized for being ‘loud and annoying’ and for airing out her bedroom business. 

Although Don Jr. was caught smooching a Palm Beach socialite, the two are putting on an air of normalcy – pictured together on Saturday at a Rumble Creators event in Morning View, Kentucky.