Times Kimberly Guilfoyle And Donald Jr.'s PDA Gave Us Secondhand Embarrassment
Despite all the affair rumors floating about, Donald Trump Jr. and Kimberly Guilfoyle's relationship is still a go as far as anyone knows. The MAGA power couple, together since 2018, became engaged two years later (though they kept the ring under wraps till 2022). Yet despite their longevity, the two haven't quite gotten the hang of showing their affection for each other. When they pose for official photos, they tend to stand stiffly side by side, showing no indication they've been living together for years. On the occasions they do get cozy for the camera, the shots still seem staged. Is it just that they're not comfortable showing PDA in public? Or is the clumsy cuddling an indication of the true nature of their relationship? They're certainly not telling.
Take a look at these representative pics — from both professional photo agencies and Guilfoyle's own Instagram account — and judge for yourself. Is it true love, or truly cringe?
The CPAC hand-hold was hard to handle
At a 2023 Conservative Political Action Committee event, Donald Trump Jr. and Kimberly Guilfoyle tried to present a united front by walking onstage with their clasped hands raised in the air. But the physical distance between them not only spoiled the loving-couple effect, but it also made it difficult for Kimberly to keep up. The moment shown here illustrates the weirdness. Don Jr. looks as though he's pulling his fiancée toward him, and she appears unprepared to get that close. Neither of them looks especially happy, either. A far more natural technique would have been to hold hands with their arms down, then raise them after reaching center stage.
Their kiss wasn't convincing
One of the (many) memorable lines from "The Princess Bride" describes the final embrace between Westley and Buttercup: "Since the invention of the kiss, there have been five kisses rated the most passionate, the most pure." We never learn exactly which historical kisses made that list, but we're confident one of them wasn't this moment between Don Jr. and Kimberly at an unnamed event. Granted a political rally isn't the appropriate place for a blazing-hot smooch, but this peck ranks right up there with the awkward cheek-kiss moment between Donald and Melania Trump during his October 2024 rally at Madison Square Garden. Their arm placement also seems telling; rather than a full-fledged hug, the former Fox News host and the former first son maintained a respectful distance with her hand on his elbow. In all, it wasn't what one would expect from a smitten woman and the man she once called "my sweetheart...my best friend and my soulmate" in an Instagram post.
Catch of the day?
Guilfoyle shared a set of photos in early July 2023 showing "a fun getaway" to the Bahamas with her intended, plus a fishing expedition with some of their children. (Guilfoyle has one son with ex-husband Eric Villency, while Donald Trump Jr. has three sons and two daughters by ex-wife Vanessa Trump.) The pic here was apparently taken during a romantic dinner date, yet once again, the couple's stance is stagey, and their smiles forced. It's the kind of image you might expect from a bride and groom who've already posed for a hundred photos and are anxious to get to the reception. By contrast, Don Jr. seemed happier posing with the barracuda they caught — and held it more lovingly, as well.
They shared a risky fist-bump exchange
In the summer of 2020, a jittery world was learning to adjust to masking, social distancing, shuttered businesses, and open-air dining in the restaurants that weren't closed. Yet there was still a presidential race to be run, and Donald Trump's family wasn't about to let a pandemic stop them from stumping for their patriarch. Donald Trump Jr. and Kimberly Guilfoyle were regulars on the campaign trail, with Guilfoyle acting as the National Chair of the Trump Campaign Finance Committee.
But this moment from the Republican National Convention was particularly awkward. Poor Guilfoyle had to bend over and hold onto the podium in order to share a moment of support from her beloved without falling off her stilettos. Why set up this awkward encounter in the first place? If Don Jr. couldn't join her onstage for a minute, at least he could have waited until she walked off to meet her. And the fist bump itself was a strange choice. It's not as though they were limiting physical contact for their health's sake. The couple was photographed cozily posing on many occasions during the pandemic, even after Guilfoyle tested positive for COVID. Whatever the reason, it lacked something in the romance department.
The time they got too close for comfort
Um...remember all that ranting about Don Jr. and Kimberly not seeming intimate enough? Forget everything we said. This 2023 pic shared by Guilfoyle on Instagram, taken at a charity dinner benefitting pediatric cancer research, takes it to the other extreme. Yes, the happy couple finally got closer than they usually do, but check out their positioning. Don is propping his right leg on an unseen object, pressing Kim right up to his crotch. (One commenter wondered if she was "[straddling] his leg," but a closer look reveals she isn't.) The unfortunate pose also makes it appear as if Don is restraining his fiancée from moving. Considering all the sexual misconduct allegations against dad Donald Sr., the optics are super cringey. And yet again, the two just don't seem genuinely happy together. There are plenty of rumors Kimberly might leave Don Jr. if Trump loses the election; looking at this gallery of problematic PDA, we can't help wondering if they might be true.