Kimberly Guilfoyle was left stunned by photos of Donald Trump Jr sharing an intimate lunch with a Palm Beach socialite, having turned a blind eye to rumours and whispers about her fiancé’s alleged wandering eye, friends told DailyMail.com.
The 55-year-old former Fox News host and the ex-president’s son have been dating since 2018, following his divorce from his first wife, Vanessa, and announced their engagement in 2022.
The glamorous brunette, the ex-wife of California Democratic Governor Gavin Newsom, has since become a prominent member of Trump’s inner circle and campaign, often seen alongside her boyfriend at Republican and campaign events.
Now friends have exclusively told DailyMail.com that Guilfoyle was caught off guard by recent reports of Don Jr, 46, locking lips with heiress Bettina Anderson, 37, when photos were published over the weekend from the couple’s intimate lunch in Palm Beach, Florida, last month.
The source said: ‘Kimberly didn’t know anything about Bettina, or she didn’t want to know. Had she heard rumours that Don Jr was dating someone else? Probably.
Friends of Kimberly Guilfoyle told DailyMail.com that she had probably “heard rumours” about her fiancé Don Jr.’s alleged affairs, but had “looked the other way”.
A photo obtained exclusively by DailyMail.com shows Don Jr. having lunch with Palm Beach socialite Bettina Anderson, 37, in mid-August, with his fiancée Kimberly Guilfoyle nowhere to be seen.
“She’s not stupid, but it’s easy to fool yourself when you’re so committed to someone and you think that person is committed to you.”
Sources told DailyMail.com that Don Jr’s romance with Anderson is an open secret in the posh Florida city and they have been spotted enjoying each other’s company frequently.
That includes the lunch where DailyMail.com took photos showing the couple kissing several times during their meal at The Honor Bar, which is located inside the exclusive Royal Poinciana Plaza shopping mall.
The source added: ‘Don Jr. is not one to be held accountable for what he does, not to Kimberly or anyone else, except maybe his father.
“He’s pretty bold, and as smart as he is, Kimberly looked the other way.”
Despite Don Jr.’s apparent openness about his partnership with Anderson, the source says this doesn’t necessarily mean the end of his commitment to Guilfoyle.
The friend told DailyMail.com: “What happens next is anyone’s guess. Will she stay with him? Will he leave her?”
“She’s been so involved in the campaign that it would be a bad look to humiliate her. But at the convention you could see what was coming.
“Sure, they gave her a platform, but the vibe in the former president’s box was not good between her and Don. She seemed like an odd woman out.”
Guilfoyle was spotted alongside her fiancé on Saturday, just hours before DailyMail.com published exclusive photos of Don Jr. having lunch with Bettina Anderson.
Anderson, a registered Republican, often shares snaps of her glamorous Palm Beach lifestyle and was seen posing with the Stars and Stripes in a racy bikini photo on Instagram.
Sources told DailyMail.com that Don Jr’s romance with Anderson is an open secret in the posh Florida city.
The couple first got together in 2018, three months after Don Jr’s ex-wife Vanessa filed for divorce from the father of five.
At 55, the San Francisco-born former prosecutor is nine years older than Don Jr., 46, who has previously been married twice.
Her first marriage to Newsom failed in 2005 after he cheated on her with Ruby Rippey-Tourk, the wife of his then-campaign manager and former deputy chief of staff, Alex Tourk.
The couple had lunch at The Honor Bar, located inside the elegant Royal Poinciana Plaza shopping center in Palm Beach.
Three months after her divorce from Newsom was finalized in February 2006, Guilfoyle married again, this time to furniture heir Eric Villency.
Their son Ronan was born in October of that year, but the marriage was short-lived and the couple divorced in November 2009.
Since becoming Don Jr.’s partner, Guilfoyle has become an increasingly prominent member of Trump’s campaign: The mother of one frequently makes speeches at his rallies and appearances.
Until now, the couple had appeared very much in love, with Don Jr. gushing about their sixth anniversary in an Instagram post four months ago.
She wrote: ‘Happy 6th anniversary @kimberlyguilfoyle thank you for always being there no matter what the haters tell us. Love you.’
Guilfoyle responded: “You are my best friend and my soulmate. Here’s to us and the incredibly blessed life we share together. I look forward to making new memories and enjoying more adventures together.”
The intimate outing came just months after Don Jr. gushed over fiancée Kimberly Guilfoyle in an Instagram post celebrating their sixth anniversary as a couple in May.
Don Jr. and Guilfoyle, 55, live in a $15.5 million oceanfront mansion in a maximum-security housing complex in Jupiter, 19 miles north of Palm Beach. They are seen posing with his five young children and her son Ronan (far left) earlier this year at Easter.
The couple lives in a $15.5 million oceanfront mansion in an ultra-secure development in Jupiter, 20 miles north of Palm Beach.
They jointly purchased the sprawling property, which has a large three-engine boat at the front dock, for $9.7 million in April 2021, four months after getting engaged.
The Spanish-style mansion, which has six bedrooms and 11 bathrooms, is a regular setting for the couple’s lavish parties.
Neither Guilfoyle nor Don Jr have publicly commented on DailyMail.com’s revelations, but they were seen presenting a united front at an event in Kentucky on Saturday.
Following the second failed attempt on former President Trump’s life on Sunday, the two took to Instagram, with Guilfoyle again posting a message of support from Don Jr. to his father.
The original post included a screenshot of Trump’s message that was posted after the near-attack and included the caption “Again, folks!”
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