Weird Things About Kimberly Guilfoyle And Don Jr.'s Relationship That Everyone Ignores

Donald Trump Jr. and Kimberly Guilfoyle's relationship couldn't have started at a more awkward time. Vanessa Trump had only filed to end her 12-year marriage to Don Jr. three months before his romance with Guilfoyle came to light. And to make matters worse, Page Six reported that Don Jr. had cheated on the mother of his five children with "The Celebrity Apprentice" contestant Aubrey O'Day. A source alleged that the infidelity occurred while Vanessa was pregnant with their third child. Meanwhile, another insider claimed that Don Jr. told his wife that he wanted to end their union to be with O'Day.

However, it doesn't seem like the rumors fazed Guilfoyle in the slightest. According to The Washington Post, the former Fox News anchor's path crossed with Don Jr.'s at a party, and mutual friends helped them get in touch. And yet, they only reconnected when Don Jr.'s daughter, Kai Trump, enrolled in the same school as Guilfoyle's son, Ronan Villency, whom she shares with her now ex-husband, Eric Villency. 

Page Six noted that their connection turned romantic a short while before May 2018. Don Jr. made their relationship Instagram official in June with a snap of them with Poison's Bret Michaels. The couple has continued to tell the world just how strong their love is ever since. However, no amount of supposedly cute social media posts can make us turn our attention away from the stranger aspects of their romance.

Donald Trump Jr. and Kimberly Guilfoyle first sparked engagement rumors in January 2022. It didn't take an eagle-eyed observer to notice that Guilfoyle was sporting a massive rock on her ring finger in an Instagram post celebrating her beau's birthday. A few days later, an insider revealed to the Daily Mail that Don Jr. had actually popped the question on New Year's Eve 2020 but the couple kept the news under wraps. About a month later, the former "The Five" co-host confirmed their engagement in a Valentine's Day tribute on Instagram. "Falling in love with my fiancé more and more every day @donaldjtrumpjr, you're my best friend, my support system and my forever guy. Happy Valentine's Day, I love you and can't wait for the adventures that lie ahead," she gushed. 

However, one adventure that seemingly wasn't on the horizon was marriage. They still haven't walked down the aisle years after their engagement, while the couple doesn't even seem to have any concrete plans for the big day either. Weirdly enough, it seems like the outspoken political commentator has been ready for marriage for quite some time, as Page Six pointed out that she attended Mira Zwillinger's fashion show at New York City's Bridal Fashion Week all the way back in 2019. All of this may be a sign that Guilfoyle and Don Jr.'s relationship is on the rocks since it suggests a hesitancy about making a life-long commitment. Furthermore, maybe the couple decided to keep their engagement private for an entire year because they were unsure if things would last.

Audrey O'Day, the woman whom Donald Trump Jr. allegedly cheated on Vanessa Trump with, had her doubts about the authenticity of his romance with Kimberly Guilfoyle. During a 2024 appearance on the "No Jumper" podcast, O'Day confessed that she initially wrote off their relationship as fake news. "I was like, 'I don't believe this relationship for a hot second when I would watch her in interviews because that's just not his type,'" the reality star admitted before asserting that she understood Don Jr. on a deeply personal level. The singer also reflected on the controversial claims that Republican donor Michael C.Bender made about Guilfoyle and Don Jr.'s relationship in his book "Frankly, We Did Win This Election: The Inside Story of How Trump Lost." 

According to Bender, Guilfoyle told him that Don Jr. loved it when she donned a cheerleader outfit in the bedroom, per the Daily Mail. But that account didn't sound like the Don Jr. that O'Day knew. In fact, the singer disclosed, "Don would never, if I ever showed up in an outfit in front of him, he would literally make fun of me if I ever did something like that." While O'Day evidently isn't a huge fan of Guilfoyle's, Don Jr.'s ex-wife feels differently. Shortly after news of their relationship came to light, Vanessa took to X, formerly known as Twitter, to defend the former Fox News anchor and clarify that she had been separated from Don Jr. long before his new flame came into the picture.

It's no secret that Kimberly Guilfoyle and Donald Trump Jr. live an incredibly lavish life. In July 2019, the New York Post reported that he splashed out $4.5 million on a gorgeous 7-room mansion in the Hamptons for the two of them. A few months before the sale, a source informed the Post that Trump's eldest child had a non-negotiable when he went house hunting: "One of the first questions Don Jr. asked was where he could store his guns." Like most homes, the mansion didn't come with a designated gun storage area, so the couple decided to assign an entire room to Trump's substantial gun collection. While the couple is happy to spend their money on luxurious homes, they reportedly aren't as free-handed when it comes to official business spending. 

According to a 2020 HuffPost report, Trump and Guilfoyle blew nearly $65,000 worth of taxpayer funds on a two-day trip to Paris to support his father during a fundraiser. Secret Service records revealed that the couple spent a little over $23,000 on their hotel stays, more than $31,000 on flights, and $10,000 on high-security rental cars (the State Department notably capped hotel stay costs at $425). Don Jr.'s spokesperson, Andrew Surabian, defended their extravagant spending by arguing, "He gets an astonishingly high number of death threats and though he would much prefer not to be, for his personal safety, he has no choice but to be under Secret Service protection."

In October 2019, a Donald Trump adviser told The Atlantic that he had asked them for insight into Kimberly Guilfoyle's dating life several times in previous years and even remarked on her beauty. Donald apparently wasn't too keen on the idea of his eldest son, Donald Trump Jr., dating the former Fox News anchor. Likewise, two former aides divulged that he wasn't particularly supportive of Guilfoyle when she wanted to become the White House press secretary in 2017."Even he can tell the difference between the attractive women on Fox who have a little bit of substance, and those who will be derided as airheads," one claimed. It doesn't seem like Donald warmed up to Guilfoyle much in subsequent years, as the former president appeared to have the ick for her at the 2024 Republican National Convention. 

Still, his supposed dislike didn't stop Guilfoyle from shamelessly sucking up to Donald. Although the Trump family and Don Jr.'s partner appear amicable, they don't seem totally sold on her either. An insider even posited that Guilfoyle's appearance at a White House Fourth of July party stole Ivanka Trump and Jared Kushner's thunder. To prevent such awkward instances from recurring, Donald instructed his eldest son to run his guest list by him for all future events. We spotted another sign of supposed disapproval when Tiffany Trump cropped Guilfoyle out of a wedding picture on Instagram in 2022.

Kimberly Guilfoyle's impassioned speech at the 2024 Republican National Convention got the crowd up on their feet chanting Donald Trump's name. However, her fiancé, Donald Trump Jr., apparently didn't share their enthusiasm, appearing to have a rather far-off look in his eyes that made it seem like he had mentally checked out (via YouTube). Even when he joined in with the roaring applause, Don Jr. didn't look particularly enthused by his fiancée's words as he never even cracked a smile and only seemed to be doing it out of respect. Suffice it to say, Don Jr.'s lukewarm reaction didn't help the rocky relationship rumors. A few days after the event, the former "The Five" anchor took to Instagram to give herself a pat on the back for her speech and share a few photos from the RNC. 

Pretty much every shot of Guilfoyle with Don Jr. had an awkward vibe as he looked like he wasn't present in the moment and kept a distance from her for the most part. While her carousel also included a short video of Don Jr.'s speech, he didn't post about Guilfoyle at the event at all. The staunch Trump supporter's absence from her partner's social media was made even more glaring by the fact that he posted a carousel of photos from Amber Rose's speech and others. Ultimately, it seems like Guilfoyle's post was an attempt to convince us that the spark was still alive, but it totally backfired.