Cringey Moments Of PDA Between Kimberly Guilfoyle & Don Trump Jr.

The couple that stumps together stays together. At least, that appears to be the case with Kimberly Guilfoyle and Donald Trump Jr., who continue to pile on the cringey PDAs as they traipse around the USA on the Donald Trump 2024 presidential campaign trail.

Their love of locking lips makes for some decidedly awkward moments between Guilfoyle and Don Jr. Although it has to be said, you really have to go some to beat their cringe December 2020 Christmas message, where the unfortunate camera angle made it appear Don Jr. had a giant noggin' and Guilfoyle a pinhead. "I'm reasonably thankful for Kimberly," he quipped as she burst out with a high-pitched hyena laugh. "Maybe not, not so much. I don't wanna; I've managed to maintain a very low bar with Kimberly. I don't want her to get too big of an ego."

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Don Jr. and Kimberly Guilfoyle want to wish you a merry Christmas

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After Don Jr.'s engagement to Guilfoyle in November 2020, speculation that wedding bells were around the corner was rife. However, nearly four years on, a date has yet to be set, sparking reports of trouble in paradise. Guilfoyle's been working overtime in a desperate attempt to squash the split rumors. Still, their uncomfortable interactions and seemingly cold embraces have done little to help her case. We're checking out five of Guilfoyle and Don Jr.'s most cringey PDAs.

Kimberly Guilfoyle and Donald Trump Jr. were a relatively new couple when they kissed onstage at a Turning Point USA event in October 2018. So, you could be forgiven for thinking they hadn't quite got the hang of things yet, which is why it looked more like a collision of heads than a meeting of lips. Guilfoyle hung onto the sides of Don Jr.'s face for dear life while he appeared to be struggling to breathe, making for a cringey PDA.

It's unknown exactly when they met, but Guilfoyle and Don Jr. were photographed together in November 2007, along with his then-wife, Vanessa Trump, and some mutual friends. Vanessa filed for divorce in March 2018, and two months later, her estranged husband and Guilfoyle were a couple. "Don Jr. and Kimberly are seeing each other and are having a great time," a source told Page Six in May 2018. "While he wants to respect the privacy of his family, he is getting divorced, and he enjoys Kimberly's company."

They went Instagram official in June 2018, posing for a pic with Poison frontman Brett Michaels. By August, Don Jr. and Guilfoyle had coined cutesy nicknames for each other. According to Page Six, his was "Junior Mint," and hers was "Pooh Bear." They also created a joint nickname. "Hashtag, Donberly," Guilfoyle announced to the Turning Point crowd. "Here's the thing with celebrity nicknames; you can't just come up with your own," James Corden decreed.

Donald Trump Jr. looked like he wasn't feeling it when Kimberly Guilfoyle planted one on him at the October 2019 Sportsmen for Trump panel discussion in San Antonio, Texas. Guilfoyle pulled him in for a smooch, holding onto his shoulder, but he looked like he couldn't get it over with quickly enough as he touched her elbow lightly.

That month, Don Jr. and Guilfoyle sat down with The Daily Caller to discuss life on the campaign trail. "I love it, it's been a really exhilarating experience, I feel super passionate about it," Guilfoyle said. "I'm excited when I wake up in the morning, I go to bed at night, about just the incredible experiences.

"From 2016 on, it's been amazing," Don Jr. said. "But ultimately, I do this because I see the results. I'm not making any money off of it." As is often the case, his claim is somewhat dubious. After his father, Donald Trump took office, Don Jr. became hot property on the speaking circuit, earning up to $100,000 for domestic and overseas gigs, which was potentially problematic. "The paid speeches do not break any laws, but create a risk of Trump's children getting unethical benefits from their father's role as president," Noah Bookbinder, the executive director of Citizens for Responsibility and Ethics in Washington, told NBC News in October 2017. "They also open the possibility of foreign governments using access to Trump's children as a way to influence U.S. policy."

Kimberly Guilfoyle and Donald Trump Jr. were still on the campaign trail in January 2021, joining Donald Trump at a Republican National Committee Victory Rally at Dalton Regional Airport in Georgia. The couple was still bringing the cringey moments of PDA, too. Guilfoyle was all in as she pulled Don Jr. in for a romantic on-stage kiss, but his mind was clearly on something else as he looked over her shoulder, eyes wide open.

Their awkward interaction didn't exactly scream love's young dream. Still, Guilfoyle and Don Jr. gushed about their amazing romance in an interview with "Extra" in December 2020. They dodged questions about wedding plans but insisted they were in it for the long run. "Committed in our hearts forever for life, which is very sweet," Guilfoyle said. "We've been a little focused," Don Jr. explained.

Meanwhile, they explained their often crazed and impassioned speeches. "We're both very fired up, we're high energy," Guilfoyle shared. "I'm a proud American. I love this country, and I wanted to put it all out there." Well, she certainly didn't disappoint with her high-decibel, ranting, and raving speech at the Republican National Convention in August 2020. "By the way, this is who I had to be with in quarantine for four months," Don Jr. interjected as Guilfoyle laughed maniacally. "We like the passion, and she brings the heat."

Kimberly Guilfoyle looked like she was trying to suck the chrome off a car bumper when she clung on tightly to Donald Trump Jr.'s arms and pulled him for a kiss at the Orlando, Florida, Conservative Political Action Conference in February 2021.

Some couples would tire of being together 24/7, let alone doing it while traveling from one city to another. Melania Trump is rarely, if ever, seen by Donald Trump's side as he speaks at campaign stops around the country. But Don Jr. and Guilfoyle thrive on it. They share a passion for his father and for getting the word out, something he really appreciates about her.

"She was the first person to be like, 'Hey, I'm all in on Trump.' You know, before even the biggest names and the biggest pundits that are now the biggest Trump boosters out there, she was there before all of them were. She got it; she knew what my father was about, she knew what the family was about, and she's been out there and just does an incredible job," Don Jr. told AM 1450 KMMS in October 2018. "No one has more energy, no one has more fire."

Perhaps the most cringey moment of PDA between Kimberly Guilfoyle and Donald Trump Jr. was their interaction at the Republican National Convention in July 2024. She posted a GIF on Instagram (complete with drawn-on love hearts) showing her and Don Jr. hugging onstage behind Donald Trump. He looked like a kid being hugged by his grandma rather than his fiancée, lightly patting her back while she enveloped him. The overall impression was that he's just not into her.

So, is Donberly's love dimming? We spoke to an expert to get their opinion. "It is so common for that hot and heavy PDA to wane after the start of the relationship, but a more comfortable and loving PDA takes its place," Susan Trombetti, matchmaker and CEO of Exclusive Matchmaking, told Nicki Swift. "It goes from can't keep your hands off someone in a passionate way to handholding."

"In the beginning, it might be just having to constantly touch the other in small ways, in the same way you mention their name in every conversation when you are smitten with someone in the initial phases of a relationship," Trombetti explained to us. "Over time, PDA wanes, and more loving touches that are the everyday intimate connection and threads of a relationship start happening. It's more quiet but just as constant and wonderful."