Awkward Kimberly Guilfoyle & Trump Jr. Pics That Should've Stayed In The Camera Roll

Kimberly Guilfoyle and Donald Trump Jr. were MAGA's hot new it couple when they burst on the scene in 2018. They racked up the column inches as they took their love show on the road, performing at rallies all across the USA, stumping hard for Donald Trump. It was clear right off the bat that they #Donberly had an unquenchable thirst for publicity and that they'd never met a camera they didn't like. So, it's puzzling why so many of their photos together totally verge on the awkward and the cringe.

There are a lot of weird things about Guilfoyle and Don Jr.'s relationship that everyone ignores. But it's hard to turn a blind eye when they're laid out on social media for everyone to see. That said, Guilfoyle's Instagram vs. reality moments are few and far between, often making it difficult to ascertain what's an authentic couple's trainwreck and what's not. Then, there are the countless times that Guilfoyle has taken Photoshopping her pics too far, making for some decidedly uncomfortable and awkward photos.

The former Fox News host's social media is packed with pictures of her and Don Jr. living their very best (heavily filtered) lives. However, no amount of manipulation can make the photos appear natural and relaxed. From dead deer to getting down with the Kid to a Halloween horror, there are some awkward Guilfoyle and Don Jr. photos that most definitely should have stayed in the camera roll.

Kimberly Guilfoyle and Donald Trump Jr. really brought the awks with the carousel of Memorial Day weekend pics she posted on Instagram in May 2019. "Truly a beautiful and blessed Memorial Day weekend. Giving thanks to the men and women that serve this country faithfully and for the sacrifices that their families make each and every day," Guilfoyle wrote in the caption. She added a "live simply" hashtag, which would seem a little out of place given that she was dolled up to the nines and looked like she was heading out for a night on the town rather than a wilderness weekend.

The photos documented the couple's fun time being at one with nature. Trump seemed to be especially enjoying himself as he leaned over his fiancée's shoulder, thrusting a selection of dead fish at the camera with a feral look in his eyes. In one of the photos, Guilfoyle, hair in pigtails, is captured pretending that she's having a great time as she stands hip-deep in water, brandishing a fishing rod. In another, she poses with a pal, hand on hip, and grinning at the camera.

Detractors lit up the Insta comments. "A trout holding a fish," one wrote. "Don't look like Kim s cup of tea lol," another observed. Will you be accompanying this creep to Africa when he slaughters endangered species again?" a third asked.

Few things look more awkward than a bunch of middle-aged white people pretending like they're down with the kids — even if they are hanging out with an actual kid: well, Kid Rock anyway. Still, Kimberly Guilfoyle and Donald Trump Jr. gave it their very best shot in December 2022. Their efforts were captured on camera, and the resulting pic was appropriately cringe.

In the shot, Rock is crouched in a kind of rapper pose, showing off his giant diamond and gold ring, while Guilfoyle is full-on jazz hands. However, a pursed-lip Trump steals the show as he clutches a fat cigar and busts out with his best baller shapes. Because nothing screams "gangsta!" like a pink shirt tucked into waist-high brown belted chinos, camo slip-ons, and.... Kid Rock. "Blessed evening at our home for our 2nd annual Marines Toys for Tots Christmas Boat Parade Party. Thank you to all of our friends and community who generously gave toys and much needed funds filling 3 boats of happiness and love for children in need," Guilfoyle captioned a selection of photos from the big night.

"Kid rock is the best you can do," a commenter mocked. "Daaaaaad the kids are at it again," another joked. "Noone is cooler than Kid Rock!!" a third claimed, seemingly without even a hint of irony.

Donald Trump Jr. went all out to celebrate his dating anniversary with Kimberly Guilfoyle in April 2024. "Happy 6 year anniversary @kimberlyguilfoyle thanks for always being there no matter what the haters are throwing our way. I love you," he declared on Instagram. It was short and sweet, but what Don Jr. lacked in word count, he more than made up for in photos. He posted a carousel of awkward pics featuring himself and Guilfoyle, encapsulating their heady romance.

They included a selection of stiff, formal shots mixed with the thrusting dead fish pic and a gun-toting 'copter shot. Firearms are clearly an integral part of the couple's relationship, and Don Jr. went all out in honor of their big day, wielding a semi-automatic FN PS90 — presumably because the even deadlier FN P90 sub-machine gun isn't available for civilian use — yet.

Meanwhile, Guilfoyle stood awkwardly by her fiancé's side, clasping a pair of aviators and grinning proudly. It makes for a decidedly strange couple's photo, even by Trump family standards. "I don't get these two. She's like a lot older sister," a commenter wrote. "What an uncomfortable looking couple," another opined. "You two deserve each other. Both of you are unpleasant to look at," a third chimed in.

Donald Trump Jr. and Kimberly Guilfoyle's 2019 Halloween pic really puts the A in awkward. Don Jr. pretty much dialed it in, clad in his usual weekend attire of choice: a camo cap, suit, and sneakers, paired with an oversized deadly weapon (although, in this instance, he swapped the semi-automatic for a Hoyt Carbon defiant turbo crossbow). Meanwhile, Guilfoyle stopped by the Dollar Store on her way back from work to buy a cheap witch costume, complete with a pointy hat, for the night.

Guilfoyle sticks out her ample chest in the couple's shot while Don Jr. brings up the rear, grinning sheepishly and fiddling with his bow. "Happy Halloween," she captioned the photo on Instagram and geo-tagged "The Swamp." Guilfoyle used the opportunity to promote Don Jr.'s book "Triggered," and in case anybody was confused by their get-up, she added #witchhunt. Guilfoyle also included #KAG2020 in honor of Donald Trump's short-lived campaign chant, "Keep America Great." Don Jr. posted even cringier pics on his account.

"Witch Hunt!!! Happy Halloween folks! With all the b******t the Democrats are throwing out there we just couldn't resist," he captioned it. Ever the freebie opportunist, Don Jr. tagged the manufacturers of his sporting gear in the pic. "Daddy's little man loves to play dress up. You look f*****g ridiculous," a hater wrote. "Fake t**s. Fake lips. Fake relationship," another sniped. "Oh look terrorist and the Wicked Witch of the West," a third commented.

One of the significant themes in Kimberly Guilfoyle and Donald Trump Jr.'s album of awkward pics is camo wear, firearms, and an inordinate number of slaughtered animals, proving that the couple who hunt together stay together (or not, if rumors are to be believed). This is showcased in a January 2023 photo that captures the couple crouched down, grinning proudly with a dead buck deer — and Erik Trump.

In the heavily filtered image, Guilfoyle, with full makeup and blown-out hair flowing in the breeze, is sandwiched between the two bros as Don Jr. holds up the dead animal's head, resulting in a pic fit for the Trump dynasty album. "Wishing @erictrump the happiest of birthdays! You are a wonderful father to Luke and Carolina, husband to @laraleatrump, brother and friend to all who know and love you! Here's to the absolute best 2023!" Guilfoyle captioned a carousel of images, including the hunting shot, assorted family images, and a photo of her, Don Jr., Erik, and Lara Trump crowding around a decidedly "over it" looking Santa Claus.

Sadly, not all of Guilfoyle's followers were filled with the Christmas spirit. "You should all be ashamed of yourselves, for so many reasons," one wrote. "Talk about a disturbing group of really bad people! This is the true crime syndicate!" another charged. "Just plain wrong to kill and pose with this beautiful animal!" a third declared.