Kimberly Guilfoyle & Donald Trump Jr.'s Most Awkward Comments About Their Romance

Kimberly Guilfoyle and Donald Trump Jr. made headlines back in 2018 when they were spotted attending parties and enjoying nights out on the town together. While Trump Jr. was freshly divorced from his then-wife and mother of his five children, Vanessa Haydon, Guilfoyle was already twice divorced as well, having been previously betrothed to politician and eventual California governor Gavin Newsom and businessman Eric Villency, respectively. 

Since then, the couple has seemingly enjoyed many wonderful times together. In 2020, Guilfoyle subtly announced they were engaged to be married. "Tonight was extra special celebrating @donaldjtrumpjr's birthday. Don, you are strong, smart, courageous, funny and the love of my life. I can't wait to spend the rest of our lives together. Love you," Guilfoyle penned in a revelatory Instagram post along with a photo of the couple smiling ear to ear while she donned a large and in charge sparkler on her left hand. Alas, the famous fiancees have raised a few eyebrows over the years for their awkward comments about one another, adding to the long list of strange things about Guilfoyle and Trump Jr.'s relationship.

Let's start off with addressing the elephant in the room that is Donald Trump Jr.'s nickname for Kimberly Guilfoyle. During a rather disastrous appearance on ABC's "The View" in 2019, Guilfoyle hinted that Trump affectionally refers to her as "Mamacita." During a heated debate about Trump's decision to tweet out the name of an alleged whistleblower, Guilfoyle worked overtime to keep everything cordial. "Okay, it wasn't the most prudent decision to retweet an article," she admitted (via the Washington Post). "I did come out of the bathroom and say, 'I left you alone for 10 minutes; what happens when 'Mamacita' is gone?'" she revealed. Could this have been the one, rare moment the ladies of "The View" were rendered speechless?

But that's not all. It appears Trump has another nickname for Guilfoyle and she has one for him too. As reported by Page Six in 2018, Trump also refers to his future wife as Pooh Bear, while she refers to him as Junior Mint. "She said something like, 'Don, you're so sweet,' and then sent a picture of Junior Mints," a source told the publication about the saccharine sobriquet.

Haters gonna hate. On April 24, Donald Trump Jr. and Kimberly Guilfoyle took to Instagram to relish their six-year dating anniversary, with their posts proving they live on different planets. While Guilfoyle's tribute was more thoughtful, Donald Jr. instead gave their supposed haters a nod. "Happy 6 year anniversary @kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way," he penned. "I love you."

As one can imagine, many Instagram users had a field day in the comments section with Trump Jr.'s uncanny ability to take what should be a sentimental tribute and find a way to seamlessly slide in a jab at the couple's naysayers. "'The haters'? @donaldjtrumpjr No one spews more hatred than you, Junior. (Well, maybe your daddy.)" one user wrote. Still, another seemingly sympathized with Trump Jr.'s plight. "CONGRATULATIONS, I KNOW IT'S NOT EASY WITH THE HATERS, THAT'S HOW I ENDED UP DIVORCED!" the user penned. Yikes! Alexa, play "Another One Bites the Dust" by Queen.

Potential father-in-law, future father-in-law. Potato, po-ta-to. In an awkward made-for-TV moment, Kimberly Guilfoyle went head to head with television host Greg Kelly during a 2023 appearance on Newsmax (via The Independent). Right out of the gate, Guilfoyle seemingly took offense to Kelly's use of the term "potential father-in-law," when referring to her fiance's father, former president, Donald J. Trump. "Potential? Future father-in-law. Jesus," she sneered. Nevertheless, Kelly persisted. "Is it sealed? Do we have a date?" he pressed to which Guilfoyle replied, "Uh, not that I'm sharing on the air." And, scene!

It should be noted, however, that this isn't the first time someone has questioned Guilfoyle and Trump Jr.'s intent to make good on their engagement and tie the knot once and for all. "Just wondering when Don Jr. is going to marry his 'fiance' Kim Guilfoyle. I guess getting just the right caterer sometimes requires a long wait in line, one Twitter user quipped about the lengthy engagement.

Donald Trump Jr. is just happy that Kimberly Guilfoyle puts up with him. No, really. On April 24, 2022, the businessman and chip off the ol' block took to his Instagram to commemorate his four-year dating anniversary with Kimberly Guilfoyle. "Can't believe she put up with me for 4 years folks. Happy anniversary KG I love you," he penned. But that's not all. Like clockwork, one year later, on April 24, 2023 he penned an eerily similar celebratory post. "Happy 5 year anniversary to my my love @kimberlyguilfoyle... what a ride, and if you can put up with my a** for that long with everything they've thrown at us 5 years is just the start of it. I love you," he wrote. 

Fortunately for Trump Jr., it appears that Guilfoyle not only puts up with him, she loves doting on him. "I go out of my way to make sure he has everything he needs — making coffee in the morning, cooking our favorite meals, doing our families laundry, and caring for our home," she revealed during a December 2022 interview with Metropolitan Luxury Magazine. "He appreciates this about who I am, and I respect him, his strength, loyalty, and his undaunted courage."

Donald Trump Jr. playfully called Kimberly Guilfoyle a broad during what was meant to be celebratory birthday post. "Happy birthday to the best broad ever @kimberlyguilfoyle (inside joke but she knows that's the highest form of compliment ever!) so relax Karens. 29 only comes once or twice so enjoy it princess. I love you." Suddenly, "Mamacita" and "Pooh Bear" don't sound so bad... 

All joking aside, the post probably reminded all of the so-called Karens about Trump Jr.'s famous father's infamous "Access Hollywood" tape scandal wherein he was caught boasting about grabbing women's private parts without their permission. At the time, Trump Jr. had chalked his father's unsavory remarks up to merely a "fact of life." He added, "Obviously he's not happy about that, but I think we all probably know guys who have had conversations with guys who go a little bit in that direction" (via CNN).