Strange Things About Kimberly Guilfoyle And Donald Trump Jr.'s Relationship

The First Family is chock full of solid relationships. You have President Donald Trump and Melania Trump at the top of the love pyramid, who you can't deny have set a great example on how to weather a marriage storm successfully. The senior Mr. and Mrs. Trump have been through everything from gold-digging rumors to infidelity, yet they remain united. Or seem to be at least.

Most of the Trump kids have followed in their parents' footsteps when it comes to relationships. Both Ivanka Trump and Eric Trump appear to have stable marriages, and Donald Trump Jr. looks like he wants one badly. His wife, Vanessa Trump, filed for divorce in 2018, and he did go through that whole Aubrie O' Day cheating scandal (circa 2011). However, he seems to be on the straight and narrow ever since. 

Don Jr. coupled up with former Fox News host Kimberly Guilfoyle shortly after Vanessa filed for divorce, and the couple has been proudly showcasing their love all over social media ever since. Prior to becoming Don Jr.'s live-in girlfriend, Guilfoyle was married to California Governor Andrew Newsom and furniture heir Eric Villency (who's the father of her son Ronan). She seems to like men in politics, and Don Jr. definitely fits that bill. While it's nice to see the president's eldest son happy again, there are a few peculiar things about his latest relationship that are hard to ignore. Keep reading after the jump to see what we're talking about.

You would think someone who just got divorced would want some alone time before they jumped right back into the dating pool. Not Donald Trump Jr., apparently. If you look at the timeline, he didn't waste much time on the singles market after his wife, Vanessa Trump, filed to end their 12-year marriage in March 2018. The divorce was finalized in less than a year (most likely because of a prenuptial agreement). However, Don Jr. was already months into his new relationship with Fox News host Kimberly Guilfoyle when he officially became single. Why waste any time, right?

On May 9, 2018, Page Six broke the news that Don Jr. and Guilfoyle had been already "dating for a few weeks." In short, the new girlfriend announcement came only two months after the divorce announcement. Talk about jumping back in!

The couple was first spotted arriving together to a party for President Donald Trump's new ambassador to Germany. A source confirmed the romance to the outlet saying, "Don Jr. and Kimberly are seeing each other, and are having a great time. While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly's company." Around the same time, Daily Mail revealed that the couple was "crazy about each other." Sources told the outlet the two weren't trying to "hide" their romance and were pretty openly affectionate. 

Donald Trump Jr. and Kimberly Guilfoyle knew each other long before they started dating. While we can't confirm exactly how they went from friends to lovers, we can definitely say that the pair ran in the same circles since at least 2007, as evidenced in these throwbacks photos regurgitated by the Daily Mail.

In one throwback photo from 2008, Don Jr. has his arm around his then-wife, Vanessa Trump, while Guilfoyle and her second ex-husband Eric Villency are standing next to them, smiling joyfully. We're not sure if the foursome was on a double date in this picture or if it was just a random photo-op, but the two couples knew each other well enough to take a snap — so there had to be some sort of acquaintance-ship if nothing else.

While it's interesting to see Don Jr. and Guilfoyle photographed alongside their ex-spouses, it's even more interesting to see a throwback photo of Guilfoyle with Don Jr.'s ex-wife Vanessa. In this snapshot, Vanessa has her arm around Guilfoyle, and the women's heads are positioned against each other (as if they were besties). While this photo was taken long before Guilfoyle moved on to Vanessa's man, it's still thought-provoking to reminisce over. *Say cheese*

Kimberly Guilfoyle wanted a spot in President Donald Trump's inner circle long before she came to the family dinner table as his son's plus one. Sources say she first tried to become a Trump insider in 2016 when she lobbied for a job with her now-boyfriend's father. According to Mediaite, Guilfoyle was spotted walking into Trump Tower in October that year, creating rumors that she was in talks for a job on papa Trump's communications team.

Sean Spicer wound up getting hired — but Guilfoyle's name came up for the position again in 2017. At the time, Guilfoyle told The Mercury News that "it would be an honor to serve the country." Fox News didn't seem to want to let her go though, telling the AP she was "under a long-term contract."

According to The Atlantic, the real truth is, "Trump had shown little interest" in her then. "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," a source revealed. The President obviously didn't think she was too much of an "airhead," though since he eventually gave her a spot on his roster. It just so happened to be after she started dating his son. According to a HuffPost source, her chances of getting the job prior to dating Donald Trump Jr. were "less than zero, if that's possible."

Every girl wants their boyfriend's parents to like them, and Kimberly Guilfoyle looks like the poster child for winning over a man's folks. President Donald Trump has basically branded her as the face of his re-election campaign, and she appears to be a welcomed member of the fam before she's even scored a ring.

However, sources say the president wasn't always thrilled about Guilfoyle dating his son. "The family was friendly to Guilfoyle in person, but there were signs of disapproval," The Atlantic alleged in 2019. A source told the outlet that the "fawning press coverage" Guilfoyle and Don Jr. initially drew at a White House Fourth of July event was not well received. The new couple supposedly outshone Ivanka Trump and Jared Kushner that day, which is, apparently, a no-go. "Don was contacted by an official informing him that he would need to clear his guests the next time he visited. And as Thanksgiving approached, the president made it known that Guilfoyle wasn't welcome to join the family at Mar-a-Lago," The Atlantic reported.

Spokespeople for Don Jr. and the White House denied the claims. However, the same article said the President might have had another reason for being irked by the relationship. "Over the years, Trump had frequently made suggestive comments about Guilfoyle's attractiveness," according to the publication. The media outlet claimed that President Trump "more than once inquired about who [Guilfoyle] was dating."

While most folks get to fight for legroom and an armrest when they travel commercially, the rich and famous don't typically have these problems. One perk of having money is traveling large, so we are not surprised that Kimberly Guilfoyle and Donald Trump Jr. do just that when they jet around the globe.

According to US Secret Service records, the couple spent $23,036 on hotel rooms and $31,104 on air travel on a two-day trip to Paris in July 2018 (via HuffPost). Let's not forget about the $10,303 they spent on renting three vehicles, as reported by the same source. As the outlet said, "The hotels wound up being so expensive that the agency had to seek an $8,575 'lodging variance' to make up for the overrun beyond the $14,460 estimate." Apparently, a hotel in Paris shouldn't cost the State Department more than $425 per day — or it's considered an indulgence. They missed that mark by a mile (to put it mildly).

American taxpayers typically foot the bill for some of these fancy-schmancy trips. But, a spokesman, who defended the couple's reconciled expenses, told HuffPost that Don Jr. needs the extra security due to "unhinged conspiracies" created by "left-wing outlets."

"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," the spokesman said.

Regardless of how she really felt about her ex-husband moving on so quickly, Vanessa Trump was quick to stand up for Kimberly Guilfoyle when her relationship with Donald Trump Jr. was scrutinized in the press. It all started on June 12, 2018, when the Daily News suggested that "the sex-scandal-plagued" Fox News should re-consider Guilfoyle's job if they wanted to "maintain even the slightest shred of journalistic integrity."

"Now that Kimberly Guilfoyle is reportedly having sleepovers with Donald Trump Jr., the Fredo Corleone of the Trump boys, while she's reporting on him, his father, his father's sex scandals, and the Mueller investigation, what Fox News — that fair and balanced network — should do is bust her down to courtroom reporter. Or fire her," the Daily News wrote. The media outlet stated that Guilfoyle "can't report on the most powerful family in the country while dating one of them." 

In a move that showed nothing but the highest form of class, Vanessa came to Guilfoyle's defense, writing on Twitter, "The lengths people will go to attack a woman simply because she's dating Don. We've been separated for over 9 months and respect each other's decisions & privacy. We'll focus on raising our great kids. Would be nice if the press did the same rather than obsess over our pvt lives." Trump Jr. also came to his girlfriend's defense, retweeting a Mediaite article calling the Daily News story "absurd." 

The 2020 Republican National Convention was all about President Donald Trump, but it also gave some of his biggest supporters a chance to shine. Most of the invited speakers did just that. Then there was Donald Trump and Kimberly Guilfoyle, who gave what we'll call odd performances. We're not sure if these two practiced together or what, but they were each scrutinized (for totally different reasons) after they took the stage. Here's what happened.

We'll start with Guilfoyle's speech first since it was the LOUDEST. She basically shouted the entire six-minute speech (in an empty room). The volume was so awkwardly loud that memes popped up all over social media after she spoke. 

Then there was Don Jr's. speech, which had great content, but as Late Show host Stephen Colbert put it, his "sweaty face and wet, bloodshot eyes" kind of took away from the message. "Either he's high, or that's what happens when you live in the splash zone of Screamin' Guilfoyle. Just bring a poncho," joked Colbert. Actress Debra Messing also commented on Don Jr.'s performance on Twitter, writing, "WOW. @DonaldJTrumpJr you should have held back a little there. And one word: Visine. #DonnieDrugs."

Don Jr. called the comments "pretty ridiculous" In an interview with Fox and Friends host Steve Doocy, adding that, "When they can't attack the delivery, when they can't attack the substance, they gotta attack something," (via HuffPost).

It's no secret that Donald Trump Jr. is an avid gun enthusiast, enjoys hunting, and is passionate about his American right to bear arms. What you may not know is that he and Kimberly Guilfoyle almost didn't buy the Hamptons home they now own because it didn't have a gun room in it, according to the New York Post. A source told the outlet, "One of the first questions Don Jr. asked was where he could store his guns." We can't help but wonder how common a "gun room" is on people's must-have house hunting lists?

Nevertheless, the couple wound up going under contract for the 9,200 Bridgehampton home anyway with a plan to add a custom gun room later, according to the same source. A source told the outlet that the property's 25-acre kettle pond helped "seal the deal" on the $4.5 million property.

When you dig into it, the property sounds like it's worth every bit of the $4.5 million they paid for it (especially since it's in a prime Bridgehampton location). The house sits on 3.9 acres, is in a gated community, has a pool with a waterfall, and is close to the beach and shopping, according to Realtor.