Awkward Donald Trump Jr. Moments That Made Us Cringe

Donald Trump Jr. wasn't a nationally known political figure before 2016; instead, he was perhaps best known for his appearances on his dad's reality TV show "The Apprentice." With his father's foray into politics, however, Don Jr. has leaned into becoming a conservative firebrand. Don Jr. wrote a book called "Triggered: How the Left Thrives on Hate and Wants to Silence Us" and he has a podcast also called "Triggered." He may have even had a hand in his father picking Ohio senator JD Vance as his running mate — Vance and Don Jr. have become close friends in recent years. 

Like anyone in the public eye, Don Jr. has had his fair share of awkward moments, including some with Kimberly Guilfoyle, his fiancée. That being said, there do seem to be some instances that are particularly cringey because they seem like they could have so easily been avoided. From his awkward posing for an article in The New York Times to oddly rambling speeches and interviews to weird social media posts, these five Don Jr. moments stand out as some of the worst.

In a March 2017 article about Donald Trump Jr. in The New York Times, they used a picture of Don Jr. looking pensive and sad as he gazes into the distance and sits on a tree stump wearing what seems to be a lumberjack-inspired look — a plaid shirt, jeans, and what seem to be new mountaineering boots. He may actually be an avid outdoorsman who likes hunting and fishing, but this particular picture makes it look more like he's cosplaying as someone who's actually comfortable being outside. Our guess is that Don Jr. gave the OK to the photo, and even if he didn't, he made the face, wore the outfit, and held the pose that ended up launching all sorts of memes and plenty of creative criticism of pretty much everything about the picture.

Local Man Once Shook Hands With Eddie Vedder pic.twitter.com/HW1s6DOVWY

— brandonstosuy (@brandonstosuy) March 18, 2017

A lot of people online noted how it looked like Don Jr. didn't really know how to sit. One person wrote on X, formerly known as Twitter, "Tfw your assistant picked you up and carried you to a stump in the woods to not scuff your boots."Another person posted, "Donald Trump Jr. looks like a scarecrow that a bank leaves on a foreclosed farm." Some compared him to the main character at the end of "The Giving Tree" by Shel Silverstein who keeps taking from a tree until all that's left is a withered stump. All in all, the pic got a lot of attention and none of it seemed good.

In 2018, Donald Trump Jr. went to New Delhi, India to help promote sales of Trump-branded luxury condos and apartments in the country. His visit raised questions about the ethics and potential conflicts of interest of the president's son doing business deals in another country. Beyond that issue was the awkward moment that came during an interview with a local TV news channel CNBC-TV 18 where Don Jr. seemed to be trying to pay a compliment to impoverished people in India but succeeded solely in putting his foot in his mount. 

Here's what he said: "I think there is something about the spirit of the Indian people that is unique here to other parts of the emerging world. You go through a town ... and, I don't want to be glib but you can see the poorest of the poor and there is still a smile on a face," via NBC News.

Many saw the comment as particularly patronizing, and showing how out of touch and spoiled Don Jr. really is. One person wrote on X, formerly known as Twitter, "Is he saying that the poor are happy so it is all right to be poor and live in substandard conditions? Maybe Junior should give it a try."

Donald Trump Jr. has been interviewed many times on Fox News, often to speak in praise of his father Donald Trump and/or against Democrats. Don Jr.'s Fox News interview after the second 2020 presidential debate had Don Jr. behaving so strangely that it caught the attention of Jimmy Fallon, and he talked about it on his late-night show. Fallon shared a clip of Don Jr. speaking remarkably quickly during the interview — Don Jr.'s fast talk could be a sign of nerves — and bringing up a conspiracy theory that the FBI is anti-Trump. 

Fallon quipped, "Was he double parked?" in response to Don Jr.'s rapid-fire delivery. "He sounds like a kindergartener who can't wait to tell you about his day," via "The Tonight Show With Jimmy Fallon." Some commenters on the YouTube video thought Don Jr. must have been under the influence to be talking like that. Whatever the reason, it was all a bit too frantic for us, and you hate to keep watching it but you can't look away.

Donald Trump Jr.'s speech at the Conservative Political Action Conference in 2022 had plenty of people confused, including us. It had a couple of standout cringe moments. It started with him making a joke about Hunter Biden's expense related to Hunter's struggles with drug addiction. Then toward the end of the speech, he started shaking hands and high-fiving people in the audience and ended up seemingly going off script. At least, we're hoping that was off-script, because those attacks were awkward to watch.

He started talking about the "consequences" he'd face if he wasn't a Republican: "I'd become an artist and sell my crap for half a million dollars" (via C-SPAN). We're not sure how we follow that line of logic, that being a Republican is what is preventing Don Jr. from pursuing his artistic ambitions; it just seems to be another attack on Hunter, whose paintings have sold for six-figure amounts. Don Jr. went on to say, "I would take a billion dollars from China [...] Crack's not really my thing, but it would be fine if I was on that [Democratic] side." Huh.

Valentine's Day is generally a day when you celebrate the loved ones in your life, and it often leads to lots of lovey-dovey social media posts. Donald Trump Jr. didn't take that route in 2018. Instead, he posted on X, formerly known as Twitter, a promotion of Trump-branded merchandise in the form of a teddy bear wearing a bathrobe perched on top of a Trump plane model with the caption, "When roses just won't cut it ... #ValentinesDay." This was also the same year that Vanessa Trump and Don Jr. got divorced — we're not saying it was a direct cause and effect, but if that was his idea of romance ... yikes.

When roses just won't cut it...#ValentinesDay @TrumpStore https://t.co/aMZ0rkUhA3 pic.twitter.com/KcQFFY6Tzy

— Donald Trump Jr. (@DonaldJTrumpJr) February 7, 2018

Lots of commenters chimed in with derision about Don Jr.'s Valentine's Day suggestion. One person wrote, "Nothing says 'romance' like shoddy Trump merchandise cobbled together by exploited children in Bangladesh. My wife would leave me." Others called him out for marketing Trump products while Donald Trump was president. One critic said, "Glad your "brand" is making $$$$ off the presidency." It does seem pretty tacky whichever way you look at it, whether Don Jr. was actually promoting those as a romantic gift or that he was trying to boost the Trump brand and sell more products.