Kimberly Guilfoyle Ramps Up Scandalous Revenge Style As Don Jr. Affair Rumors Surge
Amid rumors that Donald Trump Jr. is seeing another woman, his fiancee Kimberly Guilfoyle is ramping up her revenge style (a la Princess Diana's famous revenge dress) by putting her curves on display in posts to her Instagram Stories. The former Fox News anchor took a trip to the Balkans with her fiancé in September 2024 amid efforts to drum up support in Romania and Serbia for Donald Trump's presidential campaign.
On September 25, Guilfoyle shared a trio of snaps to her Instagram Stories from her stop in Bucharest, Romania where she sported a low-cut black dress with low shoulder straps. In the first photo, she flashed a giant smile while sitting in a chair and looking away from the camera. Guilfoyle's revealing dress was on full display in the next photo, as she posed next to Don Jr., but the couple stood stiffly beside one another without making contact. The pair looked more comfortable in the third photo that Guilfoyle posted, as she looked more modest with a fur jacket draped over her shoulders as she stood with Don Jr.
It was not surprising to see Guilfoyle sporting an eye-catching outfit while in Romania, as just a week earlier she rocked a skin-baring dress after rumors that she and Donald Jr. had broken up emerged. The former "The Five" host posed in a backless purple dress from designer Oscar Lopez that he posted to his Instagram feed on September 17. Guilfoyle wearing the skimpy numbers came shortly after the Daily Mail released photos of Donald Jr. having dinner with model Bettina Anderson in August. "They were definitely on a date," a source told the outlet on September 15. After that report was released, Guilfoyle made some changes to her Instagram content.
How Kimberly Guilfoyle tried to fight break up rumors
On September 16, the Daily Mail reported that Kimberly Guilfoyle was surprised to find out about Donald Trump Jr.'s rumored relationship with another woman. "Kimberly either didn't know about Bettina — or didn't want to know," a source told the publication. "She's no fool but it's easy to deceive yourself when you're so committed to someone and believe he's committed to you," they added.
After that news broke, Guilfoyle attempted to cover up the rumors by making a PDA-packed Instagram post. Taking to the platform on September 17, she uploaded a photo carousel from the couple attending the Patriot's Day Freedom Fest. In what appeared to be an attempt to quell rumors of their relationship's demise, Guilfoyle included multiple snaps of her and Trump, including a photo where she planted a kiss on his cheek in front of the event's crowd. Not everyone was convinced the photos meant the couple were on good terms. "Did Junior bring his girlfriend ... I mean the new one?" one Instagram follower snarkily commented.
Prior to that post, Guilfoyle had not uploaded photos of her fiancé to her timeline in weeks. She had posted a snap of the couple attending a fundraiser for Donald Trump's presidential campaign on August 13 — a full month before the PDA-packed post. Before that, Junior had graced her timeline in posts on July 12 and 13, which were again taken at campaign fundraising events. One theory was that the future of the couple depended on the outcome of the election.
The election might save or end their relationship
Days after reports surfaced that Kimberly Guilfoyle's relationship with Donald Trump Jr. was on the rocks because he was seeing Bettina Anderson, political reporter Tara Palmeri weighed in on the future of the couple. According to Palmeri, Guilfoyle planned to wait out the election results before ultimately making a decision. "If Trump wins, she stays with Don Jr.," Palmeri said on the "Somebody's Gotta Win" podcast on September 18. "If Trump loses, watch Kimberly chart her own path," she added. Palmeri, who writes for Puck, claimed in an article that those within the Trump circle believed Guilfoyle's engagement could navigate the terrain of the Anderson affair rumors.
Guilfoyle may not have known about the supposed relationship with her beau, but she was familiar with Anderson. As pointed out by Page Six on September 19, photos showed the model sitting behind the engaged couple at the Republican National Convention in July. Meanwhile, Anderson appeared to address whispers about her relationship with Trump in an Instagram post on September 18. The influencer uploaded a trio of pics where she posed next to a "Private" sign. "Gossip is the devil's telephone. Best to just hang up. — Moira Rose," Anderson wrote in the caption.