Revealed: Kimberly Guilfoyle's Mar-a-Lago Power Play — How She's Battling to Win Back 'The Man Who Got Away' Don Jr.
Kimberly Guilfoyle wants to show her ex Donald Trump Jr. that he may have made a mistake leaving her.
March 27 2025, Published 1:45 p.m. ET
Kimberly Guilfoyle is making sure her ex-fiancé Donald Trump Jr. knows what he's missing on her quest to possibly winning him back, despite the president's eldest son shacking it up with socialite Bettina Anderson.
The 56-year-old attended Mar-a-Lago’s Wags to Riches Gala on Saturday, March, 22, and rubbed elbows with some of the most notable names in president Trump's corner, RadarOnline.com can reveal.
Guilfoyle is looking to 'win' back her ex Don Jr., according to insiders.
Guilfoyle wore a head-turning black gown with a sheer lace bodice which featured beaded sleeves. She matched it all up with a feathered skirt that seemed to yell, “Don’t forget what you’re missing," to her former lover.
According to Hollywood insider Rob Shuter, one party attendant said: "Kim looked amazing – and she knew it. It was giving red carpet. It was giving revenge.”
Other guests clearly noticed the U.S. ambassador to Greece doing all she can to let Don Jr. know he made a mistake moving on from her.
Guilfoyle and Don Jr. were said to be engaged before the president's eldest child was spotted with socialite Bettina Anderson.
“Kimberly’s not subtle,” a one Mar-a-Lago regular noted. “That dress? That glam? That wasn’t for the cameras – it was for (Don Jr.).”
Another added: "She looked like a Bond girl. “She wasn’t hiding – she was working the room.”
Guilfoyle was seen posing with various guests including Frasier star Kelsey Grammer.
Don. Jr. shocked his supporters when he was spotted out on a PDA-packed date with the socialite in September while he was said to still be engaged to fiancée Guilfoyle.
Following multiple reports of Don Jr., 47, and Anderson, 38, out and about together in Palm Beach, he and Guilfoyle called off their nearly four-year engagement.
The new couple then made their debut at the amfAR Gala, attended church services together, and Anderson was even Don Jr.'s date at the Mar-a-Lago New Year's Eve party. However, Guilfoyle still has all of their movements on their radar according to the new insider.
They claimed: "Kim is definitely aware. And while she’s playing nice, she’s also not going quietly."
Meanwhile, a friend of the exes said Guilfoyle has "every intention of staying close, and if that means reminding Don Jr. what he used to have? So be it.”
Since going public with his romance, Don Jr. has been spending more time in Washington D.C. due to his father's surprising election victory, however, insiders previously claimed he was also staying at Anderson's home while in Florida.
Don Jr. and Anderson have already made their public debut.
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"Don Jr. is essentially living with Bettina at her townhouse. His car is always there. Always," the source claimed.
Despite the fallout of their relationship, Guilfoyle and Don Jr. appear to be still good friends as of now. When Guilfoyle was named U.S. ambassador to Greece by Trump, her ex was quick to praise her.
He said at the time: "I could not be more proud of her and the important role she'll continue to play in my father‘s administration."
Guilfoyle also wished Don Jr. a happy birthday on January 2.
Another insider revealed Guilfoyle has "every intention of maintaining a relationship with (Don Jr.)" after their breakup.
They added: "Kimberly and Don have known each other for years and have a lot of history together so she feels like they’ll always have a connection."
