Kimberly Guilfoyle & Don Jr.'s Awkward PDA Moments Hinted Their Romance Would Never Last

Kimberly Guilfoyle and Donald Trump Jr. were a couple from 2018 until they broke up in 2024. In the beginning, Guilfoyle and Don Jr.'s loved-up behavior seemed typical of a budding romance. "He was touching her, and they were holding hands all night," an observer divulged to Page Six in 2018. Four years later, Guilfoyle indicated things were still going strong. "Don and I are a perfect match," she informed Metropolitan Palm Beach magazine in December 2022. "We share the same inner passion and fighting spirit."

However, off and on, there were also times when Guilfoyle and Don Jr.'s relationship displayed red flags that presaged their eventual ending. After five months of dating, Don Jr. joked about his discomfort with mentioning diamonds around Guilfoyle. When the couple finally did get engaged, they didn't go public with it for a year. Afterwards, Don Jr. and Guilfoyle's relationship seemed stuck in a kind of limbo as people wondered when (and if) they would take the next step and plan a wedding.

Ultimately, it didn't happen, which could be a good thing, given some signs that Guilfoyle and Don Jr.'s marriage would have been miserable. Surprisingly, even during moments when the couple looked like they were happy together and packed on the PDA, their behavior sometimes looked staged and awkward. Beyond the swirl of rumors, it was these instances that may have unwittingly provided a subtle indication of Guilfoyle and Don Jr.'s relationship difficulties.

Even during the earlier part of their relationship, Kimberly Guilfoyle and Donald Trump Jr.'s interactions had weird vibes. The then-couple indulged in a brief PDA while speaking at an October 2019 event in San Antonio, Texas. Soon after Guilfoyle referred to Don Jr. as her "special friend," they leaned in for a kiss. While Guilfoyle seemed to be giving all her attention to the brief smooch, Don Jr. kept his eyes open. Then he patted Guilfoyle's backside multiple times and rubbed his hand on her hip, exponentially increasing the awkwardness.    

In the heat of the 2024 presidential campaign, Kimberly Guilfoyle gave Donald Trump Jr. a chaste kiss on the cheek. While there's nothing necessarily uncomfortable about this exchange itself, it's all about the timing. Guilfoyle posted the pic on September 17, 2024, the day after the Daily Mail reported Bettina Anderson and Don Jr. had exchanged far more sultry PDA. While it would later be revealed that Anderson and Don Jr. had been together for months, it took until December 2024 for Don Jr. to confirm his split with Guilfoyle and finally end the uncomfortable pretending. 

In August 2020, Kimberly Guilfoyle and Donald Trump Jr. demonstrated once again that podium handoffs and awkward kisses went hand in hand. Or, in this case, hand in elbow. Between Don Jr.'s subtle downward glance and his hand on Guilfoyle's elbow, his body language isn't creating sparks. To make the situation more cringy, Guilfoyle had just recounted her first time hunting deer with her then-beau. She explained that Don Jr. told her if the hunt wasn't successful, "I would have to, like, wildly entertain him in another way." Fortunately, she didn't get into specifics. 

In January 2021, Donald Trump Jr. and Kimberly Guilfoyle were making yet another campaign appearance – one of their most commonly shared activities. Even though he's far from the podium, Don Jr. looks like he's still talking, and he doesn't appear very enthusiastic about Guilfoyle leaning in to smooch him.  While Don Jr. told the Daily Mail he was the "worst boyfriend ever" when they spent time campaigning after only five months together, he doesn't seem as concerned here. On the plus side, at least his hand positioning looks natural. 

Even back in 2019, some people were already over Kimberly Guilfoyle and Donald Trump Jr.'s compulsion to kiss in front of crowds. "Is this pda really necessary?" inquired one Facebook commenter after Guilfoyle posted a pic from a campaign rally. While Guilfoyle looks like she's concentrating on the smooch, Don Jr. looks impatient to start his speech. With her back to the audience, Guilfoyle seems to be blocking his path. In response, one of Don Jr.'s hands is braced on Guilfoyle's hip, the other dangling awkwardly at his side.