Kimberly Guilfoyle's Most Awkward Speeches Of All Time

Kimberly Guilfoyle is quite the, er, character. Once the wife of California Governor Gavin Newsom, Guilfoyle switched political sides after her divorce and eventually became engaged to Donald Trump Jr. (though rumors that Donald Jr. is having an affair are running rampant). Guilfoyle has been an avid Trump supporter for years now, and she showed just how passionate she is about the Republican cause when she delivered a fervent address to an empty room at the 2020 Republican National Convention.

Upon watching Guilfoyle's speech, one would not have guessed the room was empty. She spoke loudly and animatedly about how then-president Donald Trump would save the country if he was reelected. Many listeners, however, spent less time focusing on her speech, which seemed to be written in all caps with an abundance of exclamation marks, and more time covering their ears. "Kimberly Guilfoyle Yells Into the Void," The Cut's headline read. "Donald Trump Jr.'s Girlfriend Kimberly Guilfoyle Shouts Her Endorsement in RNC Speech" People chimed in.

Users on X, formerly known as Twitter, quickly pointed out how mortified they were by the speech. "How embarrassing. She's yelling and shaking her fist. Oh my!" one wrote. "Why is she screaming at me," another asked. Someone else added, "That's weird," while another quipped, "Crickets lmaooooo (so weird without an audience)." "She seems even more unhinged if you watch this clip with the sound off!" someone else joked. Needless to say, Guilfoyle still hasn't lived this speech down, and her speeches that followed in subsequent years haven't exactly been less awkward. On the contrary, some of them have been downright mortifying.

As the countdown to the 2024 presidential race began, Kimberly Guilfoyle's awkward speeches increased in frequency, and even some of Donald Trump's biggest fans didn't seem to care for what she had to say. In a cringe-worthy moment in February 2024, Guiloyle addressed a crowd gathered at Trump's Mar-a-Lago resort. It's clear money can't buy manners, since the gathered crowd didn't bother to stop talking among themselves despite Guilfoyle attempting to deliver a speech.

In video footage shared to X, the rowdy crowd can be heard drowning out Guilfoyle's voice, who eventually addresses it, saying, "Excuse me. If you are talking you're being very bad. You're not being best." The crowd completely ignored Guilfoyle's plea for silence and simply continued talking among themselves. This might have been the perfect occasion for Guilfoyle to use her 2020 RNC shouting voice, but alas, when she continued speaking she remained surprisingly subdued, with the audience continuing to be rowdy.

Pundits quickly took to X to discuss the disastrous speech, with one writing, "C'mon Kim Guilfoyle.... You know how to get their attention" accompanied by a video of Guilfoyle delivering her 2020 RNC speech. "Mar-a-Lago Housewives Episode? Bravo," another added. "She just told a group full of adults that they're being bad?" someone else pointed out, while another commented, "Kimberly can't read her audience. That is their best. Duh."

Kimberly Guilfoyle's unsuccessful speech at Mar-a-Lago wasn't the last of its kind. While making an appearance at the Florida Republican Party annual dinner in September 2024, the crowd was lukewarm at best during her speech. In contrast to her infamous shouting during the 2020 RNC, Guilfoyle spoke in a strange singsong voice at the event. "Americans from all walks of life have had enough of the Democrats' decline. And we are ready, we are willing, and we are able to spark a new era of American exceptionalism," Guilfoyle declared before pausing for applause, which failed to start. Eek! After realizing the audience wasn't reacting the way she'd hoped, Guilfoyle quickly added, "You can clap for that." The audience meekly joined in for some applause.

Soon enough, X was flooded with pundits commenting on the speech. "'You can clap for that' How embarrassing for her," one wrote. "@kimguilfoyle is a legend in her own mind!" someone else chimed in. Another added, "This is so painful to watch." "That was WEIRD.. I think the crowd was asleep too," one user quipped.

Aside from having a hard time getting the audience to clap at the appropriate moments during her speech at the 2024 Florida Republican Party annual dinner, Kimberly Guilfoyle also referred to former president Donald Trump as her father-in-law despite not yet being married to Donald Trump Jr. This may or may not have been a desperate attempt to hide the affair rumors following her fiance around these days.

Near the end of her speech, Guilfoyle appeared to be getting emotional as she urged the audience to "stay in the fight, stay engaged, always keep the faith." Those who paid attention until the end were baffled by what she said next. "I say this on behalf of my father-in-law, God bless you, we thank you for your support, " Guilfoyle proclaimed before concluding her speech. She then took a moment to clap for herself before leaving the stage.

The Mercury News voiced the question on everyone's lips: Did Guilfoyle and Donald Jr. secretly get married? They did keep their engagement under wraps for a year, so anything is possible when it comes to these two.

Back in 2023, Kimberly Guilfoyle weathered another awkward speech when she made an appearance at the Conservative Political Action Conference (CPAC). While her speech itself wasn't necessarily awkward, the circumstances were — when the camera panned to the audience, the auditorium was noticeably empty. The room was only at around 25% capacity during Guilfoyle's speech, and this included the area set out for members of the press. Oof! This stood in stark contrast to attendance of previous years.

Pundits took to X to discuss the meager crowd, with one writing, "Kimberly Guilfoyle at CPAC: 'All of us in this room (all 15 of us) have one message to Joe Biden...'" "First.. You don't have an audiance [sic] @kimguilfoyle," someone else added. "It looks like people were staying away from CPAC in droves!" another noted. "What a crowd!" someone else joked. "I like the tens of people applauding," another quipped, while another user added, "The crowd is yet to come!"

By the time the 2024 Republican National Convention came around, many were yet to forget Kimberly Guilfoyle's impassioned speech at the 2020 convention, so they likely held their breath when she took to the stage, hands ready on the volume button to tone things down if necessary. As expected, Guilfoyle brought her A-game, that is, what some outlets like The Independent have dubbed her "yelling voice." "Kimberly Guilfoyle is yelling again. It's very strange. She did the same thing when she spoke at the 2020 convention," one X user pointed out. "Good grief yes, 3 am and I fumbled with my remote hearing just a sec of it while trying to locate PBS News," one person responded. "I know! I almost jumped out of my seat," another added.

Guilfoyle also made some controversial claims in her speech, heavily criticizing President Joe Biden. "Joe Biden cannot lead America," she said. "He cannot even lead himself off a stage." She then insinuated that Biden was responsible for the turmoil in the world. "We are closer to World War III than any time in my life," Guilfoyle argued before addressing border control and touching on former president Donald Trump's 34 convictions. "Rioters and looters go free. While Biden and the Democrats persecute American heroes like Donald Trump," she said. This part of her speech was pretty ironic, since Guilfoyle thought Biden's age disqualified him from being president, yet touted Trump, a convicted felon, as the perfect candidate. This, of course, is nothing new in the world of politics, just like Guilfoyle's awkward speeches have become an accepted norm.