Don Jr. & Bettina Anderson Rub Their Romance In Kimberly Guilfoyle's Face With Flirty PDA

After their relationship looked questionable for months, the news of Donald Trump Jr. and Kimberly Guilfoyle's breakup became public knowledge in December 2024. Behind the scenes, Don Jr. reportedly moved on with Bettina Anderson around June, and he and Guilfoyle purportedly split in late September. Rather than time healing wounds, however, it seems to be exacerbating a sense of competition. After Anderson flexed her Valentine's plans with Don Jr., Guilfoyle tried to one-up her old flame with a hint that she, too, had a new love. Now it's back to Anderson and Don Jr., and they appear to have escalated things once again.

The couple was photographed cuddling together while they waited for Donald Trump's March 4, 2025 remarks to Congress. They sported megawatt smiles as Anderson stroked one finger along Don Jr.'s beard and gazed down at his phone. If they did take a selfie, however, neither posted it to their social media. In another pic, Don Jr. and Anderson looked happy with each other's company, arms linked.

Post-breakup, Guilfoyle and Don Jr. have often been at the same events. "Kim is still very fond of Don and kept a watchful eye out," an insider explained to People after Trump's inauguration. "She knows how beautiful and well-dressed Bettina is, and there is no question that she was hurt when her romance with Don ended." Whether Guilfoyle attended Trump's speech or saw the pics later, this latest PDA display could get under her skin.

Since their relationship first garnered attention, Donald Trump, Jr. and Bettina Anderson haven't shied away from overt displays. "They weren't exactly making out, but the kisses were romantic, and you could tell they were intimate with each other," an observer informed the Daily Mail, referencing an encounter between Don Jr. and Anderson at a restaurant in August 2024. More PDA followed as the couple was seen holding hands in December 2024, shortly before Don Jr. confirmed his split with Kimberly Guilfoyle.

While Don Jr. had compliments for Guilfoyle post-breakup, there are multiple indications the couple's breakup was way messier than its official portrayal. Even so, it appears that Guilfoyle doesn't want to completely sever ties with her ex. "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," an insider informed Page Six. In addition, there's the practical aspect that Guilfoyle and Don Jr. will have to tolerate each other anyway in certain instances, given Guilfoyle's chummy relationship with Donald Trump. Provided that Guilfoyle is confirmed as Ambassador to Greece, she'll also be working for the president.

Guilfoyle's bond with Donald may be one area where she has a leg up on Anderson. In January 2025, rumors were reported that the president and some of his family friends weren't particularly enthusiastic about Don Jr. and Anderson's romance.