Awkward Kimberly Guilfoyle Moments That Were Captured By Millions

Even though she's not an official member of the Trump family yet, Kimberly Guilfoyle has made her allegiance known, even if it meant embarrassing herself for life. "There's one solution to fixing the Biden-caused disasters and getting this country back on track," Guilfoyle firmly penned under a heavily edited photo of herself and Donald Trump on Instagram. Donald Trump Jr.'s fiancée appears to have a penchant for generating quite the buzz online and in real life, going hand-in-hand with the trademark campaigning style we usually see with the Trumps.

Prior to her association with the Trump family (she's known Trump Jr. since 2007 and has been in a public relationship with him since 2018), Guilfoyle enjoyed an impressive legal career, serving as a prosecuting attorney in San Francisco and Los Angeles, before rising to mainstream fame as a Fox News personality. While she's no stranger to sharing controversial opinions openly, such as suggesting the United States would fare better under a leader like Vladimir Putin, many of Guilfoyle's most cringe-inducing moments came about — you guessed it — after her association with the Trumps.

As one of the key players in both of Donald Trump's presidential campaigns, Guilfoyle had no problem adopting a Trump-esque approach to public appearances. Unfortunately, that has resulted in a number of awkward moments seen by millions, prompting us to recount some that are simply unforgettable.

When Kimberly Guilfoyle still co-hosted Fox News' "The Five," which could be described as a politically contentious rendition of "The View," she admitted she'd love to have a tough guy run the United States. However, she wasn't talking about physical fitness. In 2014, the panel discussed then-President Barack Obama's reaction to the growing threat of ISIS, which they felt was not intense enough. After fiercely blasting the terrorist organization, Guilfoyle turned up the heat on Obama's directive against them, awkwardly stating, "Can we get like [Benjamin] Netanyahu or like [Vladimir] Putin in for 48 hours, you know, head of the United States?" (via Media Matters for America). She continued, "I just want somebody to get in here and get it done right so that Americans don't have to worry and wake up in the morning fearful of a group that's murderous and horrific like ISIS."

Implying that any human being can single-handedly put a stop to an extremist group like ISIS, which, in 2014, had control over almost half of Syria and Iraq, is farfetched, to say the least. Additionally, awkwardly calling for a polarizing political figure like Putin, whose leadership style has been repeatedly critiqued for authoritarian tendencies, to govern a democratic nation reflects poorly on Guilfoyle's political judgment. Having conservative values is one thing, but this stance was a clear indication Guilfoyle was ripe to be taken off the air, even by Fox News.

In 2020, following the GOP's annual Republican National Convention (RNC), everybody talked about Kimberly Guilfoyle's speech, though not necessarily for the reasons the Trump family may have hoped. Guilfoyle delivered most of her lines screaming, which may have been a success in a space filled with Republicans excited to hear them. However, as the RNC was taking place at the height of the coronavirus pandemic, Guilfoyle had to pretend she was rallying up a crowd while speaking to an empty room, resulting in a cringeworthy spectacle.

Much of Guilfoyle's speech focused on criticizing others in order to laud Donald Trump. From mischaracterizing her Puerto Rican mother as an immigrant despite Puerto Ricans being natural-born U.S. citizens to accusing Democrats of pursuing Orwellian control over the American public, it undoubtedly marked one of the most awkward moments of Guilfoyle's career, if not the ultimate one.

Guilfoyle's passionate delivery made waves online, with many late-night comics taking a jab at her enthusiasm. "God, I'm glad we already had our kids because I think if I was too close to the TV, I might have been sterilized by that," Stephen Colbert quipped on "The Late Show," while "The Daily Show" host Trevor Noah joked that Guilfoyle's speech was "so loud that Canada called the cops."

Another one of Kimberly Guilfoyle's awkward public moments had close ties to terrorism — and her glaring lack of knowledge. In 2022, Guilfoyle was interrogated about the notorious January 6 Capitol riot, and her meeting with the House Select Committee did not go as planned. According to a report from The Independent, she was a key figure in organizing the rally, which ultimately turned into a full-fledged rampage of the White House, but that was not the worst takeaway from her testimony.

When questioned about her ties to Ali Alexander, a far-right activist who initiated the "Stop the Seal" campaign in an attempt to reinstate Donald Trump instead of President-elect Joe Biden, Guilfoyle thought Alexander's full name was a terrorist motto. The interviewer asked Guilfoyle whether she knew "somebody named Ali Akbar," using Alexander's birth name, which Guilfoyle had clearly never heard of. Instead of simply denying, Guilfoyle replied: "No. Isn't that what terrorists yell?"

Guilfoyle was thinking of "Allahu Akbar," a common Arabic phrase translating to "God is great" or "God is [the] greatest." While it is indeed often associated with extremism, Muslims have used the phrase in their daily prayers for hundreds of years. Even though religious extremists have distorted "Allahu Akbar" into a symbol of violence, leading many Westerners to associate it with terrorism, it was disappointing to see Guilfoyle among those vilifying it. Given her legal and political background, her lack of awareness was painfully embarrassing to even read about.

Donald Trump's recurrent efforts to evade legal consequences seem to run in the family. While Kimberly Guilfoyle has had her fair share of moments sucking up to Trump, she's no stranger to publicly standing up for Donald Trump Jr., her longtime fiancé, too, no matter how embarrassing the situation.

During a conversation with Alina Habba, Trump's attorney, in a 2023 episode of "The Kimberly Guilfoyle Show," Guilfoyle made a seemingly humorous request in the midst of the Trump family's legal woes. "Just a little favor here, if you can. Please get my fiancé and his brother off! I'd really appreciate it," said Guilfoyle, to which Habba responded with a smile and two thumbs up (via X, formerly Twitter). "[I] really don't want to have to support Junior for the rest of his life," she quipped before noticing a firework effect going off on Habba's screen. Despite Habba's explanation that it was an automated response to a thumbs-up gesture, the timing of the effect alongside the wording of Guilfoyle's request garnered heaps of laughs on social media.

Numerous X users pointed out how inappropriate Guilfoyle's phrasing was, as well as the fact that she was publicly asking a lawyer to not do their job. "Off what? I thought they hadn't done anything wrong. They really need to get their narrative straight," said one user, while another person asked, "Do they not know that we are watching them?"

Donald Trump Jr. and Kimberly Guilfoyle have been engaged since 2020, prompting many to start guessing when the two could tie the knot. The narrative even got air time in 2023 during Guilfoyle's Newsmax interview with host Greg Kelly, as reported by The Independent. As Kelly was introducing the topic they were slated to discuss, which was the Georgia election interference accusation against Donald Trump, he called Trump Guilfoyle's "potential father-in-law." Guilfoyle, visibly taken aback, laser-focused on Kelly's choice of words, responding: "Potential? Future father-in-law. Jesus."

Likely not expecting her to fixate on that particular part of his question, Kelly awkwardly admitted he didn't know about the engagement and brought up the couple's wedding plans, asking Guilfoyle whether they had a date set. "Uh, not that I'm sharing on the air," she responded. Despite Kelly's attempt to rectify the situation, Guilfoyle turned up her sarcasm meter. "We've been engaged, babe, for two years, but we'll take this breaking news alert. That's hysterical."

Judging by her reaction, the topic evidently struck a nerve with Guilfoyle, whose awkward meltdown made her look desperate to position herself as a part of the controversial family. "We need more Trumps," she made sure to tell Kelly before finally moving on to the indictment. As of this writing, Trump Jr. and Guilfoyle are the only unwed couple in the immediate Trump clan.