Donald Trump Jr. may have found a potential wifey. After his marriage to Vanessa Trump
went up in smoke in 2018, Don Jr. coupled up with former Fox News host Kimberly Guilfoyle
- and the two have been Instagram official ever since. Think these two are a match made
in heaven? Here's why this pair is a little strange.
Total rebound
You would think that someone who just got divorced might want some alone time before
jumping right back into the dating pool. But not Donald Trump Jr. He wasted no time on
the singles market after Vanessa Trump filed to end their 12-year marriage in March 2018.
The divorce was finalized in less than a year, when Don Jr. was already months into his new
relationship with Fox News host, Kimberly Guilfoyle.
"No pressure."
"No pressure, what could go wrong?"
The couple was first spotted arriving together to a presidential reception, with a source
confirming to Page Six,
"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."
Since way back…
It seems that Don Jr. and Guilfoyle knew each other long before they ever started dating.
While we can't confirm exactly how they made the jump from friends to lovers, the pair
have definitely run in the same circles since at least 2007, according to the Daily Mail.
At one particular event in 2008, Don Jr. appeared with his arm around his then-wife, Vanessa
Trump, while Guilfoyle and her second ex-husband, Eric Villency, stood next to them. We're not
sure whether the foursome went on a double date, or if it was just a random meet up,
but the two couples knew each other well enough to take a snap together.
While it's awkward that Don Jr. and Guilfoyle were photographed alongside their exes, a
possible larger story was revealed thanks to a former photo of Guilfoyle with Vanessa
Trump. In the shot, Vanessa had placed her arm around Guilfoyle, and the two appeared
basically as if they were besties. While this photo was taken long before Guilfoyle moved
on with Vanessa's ex, it still makes us wonder when the sparks really started to fly.
"I guess I'll have some popcorn, saddle up."
"Let's have some snacks."
"We'll get on Twitter and talk some smack and have a little bit of fun with it."
Presidential pass
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, sparking
rumors that she was in talks for a job on Trump's communications team.
Sean Spicer wound up getting the job - but Guilfoyle's name came up for the position
again in 2017. At the time, Guilfoyle told The Mercury News,
"It would be an honor to serve the country."
Fox News didn't seem to want to let her go though, telling the Associated Press that
she was under contract. So what was really going on? According to The Atlantic, Trump
apparently wasn't feeling her vibe. One former aide reportedly told the outlet,
"Even [Trump] 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."
"How much chocolate do you have in there right now?"
"In my mouth?"
"Yeah. Three, four, five?"
"One piece. It's actually really delicious."
But the President obviously didn't think Guilfoyle was too much of an "airhead," 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 source for HuffPost, her chances of getting the job prior to dating
Donald Trump Jr. were, quote, "Less than zero."
Not impressing the in-laws
Just about everyone wants their partner's parents to like them, and Guilfoyle seems
like the poster child for winning over her man's folks. Considering President Trump basically
branded her as the face of his re-election campaign, she appears to be a welcome member
of the fam before she has even scored a ring. But sources say the president wasn't always
thrilled about Guilfoyle dating his son. The Atlantic alleged in 2019,
"The family was friendly to Guilfoyle in person, but there were signs of disapproval."
A source told the outlet that the media coverage that 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 husband Jared Kushner that day, which is, apparently, a no-go. The
outlet reported,
"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."
"We're gonna go down to Mar-a-Lago, we'll be in Palm Beach, with, you know, with my
kids, her kid, my family, my father, it's gonna be interesting."
Spokespeople for Don Jr. and the White House denied the claims. But the Atlantic noted
the President may have had yet another reason for being irked by the relationship, with
a source claiming,
"Over the years, Trump had frequently made suggestive comments about Guilfoyle's attractiveness.
[…] [He has] more than once inquired about who [Guilfoyle] was dating."
Serious threats
While most folks get to fight for legroom and an armrest when they travel commercially,
the rich and famous don't typically have to deal with these types of issues. One perk
of having money is traveling large, so we are not surprised that Guilfoyle and Don Jr.
do just that when they jet around the globe.
According to US Secret Service records, the couple spent over $23,000 on hotel rooms and
roughly $31,000 on air travel for a two-day trip to Paris in 2018. And let's not forget
about the more than $10,000 they spent on renting three vehicles, in which to get around.
As HuffPost reported,
"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 isn't supposed to cost the State Department more than $425
per day - otherwise, it's reportedly considered an indulgence. American taxpayers typically
foot the bill for some of these luxurious trips. But a spokesman, who defended the couple's
reconciled expenses, told HuffPost that Don Jr. needs the extra security due to, quote,
"unhinged conspiracies" created by "left-wing outlets."
"Good luck with that one."
The source added,
"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."
Vanessa speaks out
Regardless of how she really felt about her ex-husband moving on so quickly, Vanessa Trump
was quick to stand up for Guilfoyle when her relationship with Don Jr. was scrutinized
in the press. It all started on June 12th, 2018, when the Daily News suggested that Fox
News should reconsider Guilfoyle's employment at the network if they wanted to be thought
of as a legitimate journalistic outlet. The paper suggested,
"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
[explicit] 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. [She] can't report
on the most powerful family in the country while dating one of them."
In a move that showed nothing but 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 [private] lives."
Don Jr. also came to his girlfriend's defense, retweeting a Mediaite article calling the
Daily News story, quote, "absurd."
The RNC
The 2020 Republican National Convention was all about President Trump, but it also gave
some of his biggest supporters a chance to shine. Most of the invited speakers appropriately
represented the party, albeit virtually, but then there were Trump Jr. and Guilfoyle, who
gave some infamously odd individual performances, which were deeply scrutinized immediately
after.
"We stand for our flag."
Guilfoyle's speech was arguably the loudest; She enthusiastically shouted the entire six-minute
speech to a mostly-empty room. The volume was so awkwardly pitched that memes popped
up all over social media after she spoke, comparing her to a foreign dictator, among
many other scenarios. Then there was Don Jr's. speech, which showcased some considerably
more substantial content, but as Late Show host Stephen Colbert put it,
"Either he's high, or that's what happens when you live in the splash zone of Screamin'
Guilfoyle. Just bring a poncho."
Actress Debra Messing also commented on Don Jr.'s performance, tweeting:
"WOW. [Donald Trump Jr.] you should have held back a little there. And one word: Visine."
"Look to the man who did what the failed Obama/Biden administration never could do and built the
greatest economy our country has ever seen."
Don Jr. called the negative comments, quote, "pretty ridiculous" during an interview with
Fox and Friends, adding,
"When they can't attack the delivery, when they can't attack the substance, they gotta
attack something."
Special request
It's no secret that Don Jr. is an avid gun enthusiast, enjoys hunting, and is passionate
about the Second Amendment right to bear arms.
"The Second Amendment means something to me. I mean, it's the Second Amendment. It wasn't
like it was some sort of crazy afterthought that happened 100 years later. I mean, it's
number two. After the pretty basic rights of freedom of speech."
But what you may not know is that he and Guilfoyle almost didn't buy their $4.5 million Hamptons
home because it didn't come with a gun room, 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."
Nevertheless, the couple wound up going under contract for the 9,200-square-foot home anyway
with a plan to add a custom gun room later. The house sits on 3.9 acres in a gated community,
and features a pool with a waterfall, as well as close proximity to the beach and shopping,
according to Realtor.com.
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