Kimberly Guilfoyle And Donald Trump Jr. Moments That Made Us Cringe

Every relationship has oddities, but when it comes to Kimberly Guilfoyle and Donald Trump Jr., these quirks can be downright cringe-worthy. From uncomfortable interviews to over-edited social media posts, this duo seems determined to make each squirmish moment worse than the previous. Let's take things back to 2018 when Kimberly Guilfoyle and Donald Trump Jr. began their romantic relationship. Don Jr. was fresh off his divorce from his ex-wife Vanessa Trump, whom he allegedly cheated on with Aubrey O'Day.

Guilfoyle, on the other hand, had been married twice already and seemed to be way more excited about Don Jr. than he was about her. Admittedly, public appearances don't always capture the true dynamic of a relationship, but Don Jr. certainly doesn't help the whispers by sharing slightly demeaning jokes about his boo. Remember when he called her a "broad" and claimed it was an inside joke (via Instagram)? Or when he said that traveling with her was a "sacrifice?" Don Jr. has often defended these comments, but we wonder why he doesn't save the teasing for their private moments and protect Guilfoyle from the internet's meanness. Unfortunately, these are only a few of the uncomfortable moments the couple has forced on us. Case in point: those cringy public pet names.

Donald Trump Jr.'s and Kimberly Guilfoyle's nicknames for each other are another awkward bit of TMI that no one asked for. During a Turning Point USA Campus rally in 2018, Guilfoyle openly called Don "Junior Mints" and promoted their self-designed ship name, "Donberly." A few months later, Page Six reported that Don's nickname for Guilfoyle was less thoughtful and a lot more squicky: "Pooh Bear."

One theory is that Don's choice references sleazy antagonist Warner Huntington III from "Legally Blonde," who called Elle Woods "Pooh Bear." "Junior Mints," on the other hand, is said to be more heartfelt. A friend of the couple reportedly told Page Six that Guilfoyle often says that Don Jr. is sweet, like Junior Mints candy. Donberly, we're certainly not judging your lovey-dovey pet names, but sharing them with us was a bit unnecessary, thank you.

Without a doubt, this image of Kimberly Guilfoyle and Donald Trump Jr., taken at the 2023 Conservative Political Action Conference (CPAC), is a strong contender for the cringest photo ever! We're unsettled by their weird hand clasp, uncomfortable postures, and strained facial expressions. Don Jr.'s entire body language seems stiff, and he almost seems to be holding a breath and pushing his chest out. Guilfoyle, sadly, doesn't look any better. And although we'd like to imagine that this image was a bad attempt at merging two separate photos, the image is real and was taken on the first day of the CPAC.

Worse still, these pictures were not the only embarrassing occurrence of the day. Don Jr. also tried to give Willy Wonka a run for his money. At one point during his speech, the former first son said to the crowd, "Alright, so little surprise for all of you. Uh, check under your seats. If there happens to be a gold chocolate bar underneath there, that's a VIP ticket to my father's reception tomorrow at CPAC" (via C-SPAN). We're unsure what his inspiration and goals for this little act were, but if he was trying to be mortifying, he certainly nailed it.

Unlike other arguments on "The View" that unexpectedly went too far, everyone could predict that Donald Trump Jr. and Kimberly Guilfoyle's visit on the talk show in 2019 would go south. The pair was scheduled to discuss Don's new book, "Triggered," but the different political stances of the guests and hosts soon caused multiple arguments. At one point, Meghan McCain gently but directly tore into Don Jr. for his father's brutish way of speaking to gold star families, fellow politicians, and even her father, John McCain, who had passed away.

Don Jr. responded that his father had been attacked more than any other president and was merely fighting fire with fire. But given Trump Sr.'s attacks at the gold star families, this answer clearly didn't satisfy McCain and her co-hosts. However, Guilfoyle was quick to come to her man's defense, explaining that she had also lost her parents and understood Meghan's pain.

"I understand your loss," she said. "Yesterday was the anniversary of my mother's passing. [Don Jr.] woke me up with a kiss and said, 'Princess, I know this is a hard day for you.'" She went on to explain that the Trumps were the real victims because their family was frequently attacked. Expectedly, the hosts weren't having it, and Whoopi Goldberg responded, "Part of being president is having a pair that can take whatever heat comes towards you" (via YouTube). 

Everyone's guilty of a little photoshop now and then, but Kimberly Guilfoyle and Donald Trump Jr. have taken it too far. A few months after going public with their relationship, Guilfoyle uploaded a picture of her and Don to Instagram. Right away, it was clear that the image had been badly over-edited. It had been airbrushed so much that there were no human-like features on either Don or Guilfoyle.

They had no pores or expression lines, and Don Jr. seemed to have an artificial sparkle in his eyes. The photo seemed so glossy and unnatural that it quickly became an internet meme. Even Chrissy Teigen took a shot at the couple on X (formerly Twitter) by reposting their picture and captioning it: "Hello, we are robots beedoo boop smiling is opening your lips and exposing your teeth until you feel a light tension on the outer corners of your mouth." Donberly might try to deny using Photoshop, but a photo editor tells The List that someone is definitely overusing the airbrush tool on their other photos.

We imagine that Kimberly Guilfoyle and Don Jr.'s shared political beliefs are a strong pillar of their relationship. However, their seeming inability to have politics-free interests is annoying and cringy, to say the least. During Halloween 2019, the couple decided to use the holiday to point out that Donald Trump Sr. was being witch-hunted. Given that he is now the first ex-president to become a felon and was found liable for E. Jean Caroll's abuse, it's clear that Trump Sr. was being hunted for valid reasons.

However, Kimberly Guilfoyle chose to dress up as a witch and Don Jr. as the hunter, using hashtags like MAGA and WitchHunt. Not only were the photos embarrassing, they were not very flattering. It's also sad that they seem unable to enjoy a simple holiday without making a political statement. It's not the first time the couple has tried to hijack Halloween for Daddy Donald either. Don Jr. also made a joke about taxing his daughter's Halloween candy to teach her about socialism in an attempt to shade Democrats. We wonder if Don Jr. and Kimberly Guilfoyle pillow talk or if they just play a tape of MAGA campaign rallies and call it a day.