Awkward Chip & Joanna Gaines Moments We Can't Ignore

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Chip and Joanna Gaines are arguably HGTV's biggest success story. Don't believe us? Chip and Joanna Gaines are worth a ton today thanks to their growing business empire, but that's not to say they haven't had some seriously awkward moments along the way. Far from keeping the deets of those hidden, however, the couple has been very open about them, speaking openly about the cringey moments in the early days of their relationship, showcasing some of their less polished moments on their shows and even admitting to embarrassing moments with other stars on talk shows. Gotta love some candidness!

To paraphrase "The Sound of Music," we'll start at the very beginning — of Chip and Joanna's relationship, that is. Despite having a strong foundation today — Chip and Joanna Gaines have five kids to boot — the early days of their courtship weren't exactly the stuff of fairytales. Joanna recounted their very first meeting on "The Tonight Show starring Jimmy Fallon" in 2023, recalling that she'd been working at her dad's tire shop when her colleagues tried to set her up with an attractive customer who was in the waiting room. Unfortunately, the young Joanna was very shy, and after making eye contact with the man — referred to as "Hot John" — she pretended she needed to walk out of the store. Luckily, it turned out that Hot John was Chip's roommate, and Chip had gone to fetch him from the shop. 

"She walked right past Hot John, thankfully, right into [my] loving arms," Chip joked, though Joanna added that even that was fairly awkward. Either way, he said, "Before you know it, the love was in the air." Talk about a sweet turnaround to a cringey moment. However, Chip wasn't being entirely truthful when he said, "Love was in the air," and the awkwardness for the couple was only just beginning.

Despite their initial meet-cute, Joanna Gaines acknowledged that her first date with future husband Chip Gaines wasn't the most romantic night of her life. In fact, she wrote in the couple's 2016 memoir "The Magnolia Story" that she'd been unimpressed by his tardiness. For reference, Chip wasn't 20 minutes behind schedule. Au contraire, as Joanna recalled in "The Magnolia Story," he was "a full ninety minutes late." 

It was so bad that after he finally knocked on the door, Joanna whispered to her friends to lie low and pretend they were out. She also wrote that she'd announced, "I don't want to go anywhere with this idiot." Her friends wanted to see him, though, and after he met her squad, Joanna was convinced to go out with him. The date went fine, and both of them admitted in "The Magnolia Story" to having been intrigued by one another (Chip believed she was a "local superstar" thanks to having starred in a commercial for her dad's tire shop, while Joanna said her intuition told her she and Chip Gaines destined for marriage).

However, Chip's bizarre antics after that date could easily have derailed things. The star has long admitted to playing mind games with Joanna — including a gag both he and Hot John decided to do to see whose love interest would cave first and call them. Unfortunately for Chip Gaines, Joanna was unmoved, and he nearly never got a second date with his now-wife. Instead of calling him first, she moved on with her life when she didn't hear back. "I picked the wrong girl to play this game with, I will say that," he admitted in a 2022 episode of "The Drew Barrymore Show," prompting the talk show host to face palm. Same, Drew. Same.

Ending off the relationship segment of Chip Gaines and Joanna Gaines most awkward moments, it bears mentioning that Chip wasn't the only one making awkward missteps early on in his courtship with the woman he'd later marry. Sure, his antics slowed things down a touch, but Chip and Joanna Gaines did go on their second date a few months after their first. A few months after that, he also said those three little words ... but was met with crickets.

Okay, so "crickets" may not be completely accurate, because as Joanna Gaines clarified to People in 2023, she did say something back. However, she told the outlet, "I was like, 'Oh, thank you.' That made him a little upset." Seems the HGTV star was understating things in that particular interview, because her recollection in "The Magnolia Story" was slightly different. Noting that they'd been playing basketball at the time, she wrote that after her snub, "He grabbed his basketball from under my arm and went storming off with it like a four-year-old." A four-year-old with a truck, that is; Joanna added that he'd driven off so dramatically that his tires actually squealed. Duh-rama!

As for Chip, he explained in "The Magnolia Story" that he'd questioned whether his then-girlfriend was "an emotionless cyborg." Thankfully, the two made up soon after, and about a year after they'd started seeing each other, Chip proposed. Granted, even that was a little on the awkward side, and Joanna shared in an early-2026 episode of "Shark Tank" that while his laidback marriage proposal had been romantic, he'd also gotten stuck in his coat while he was on one knee, and she "thought he was having a heart attack." Luckily, he was just fine, and the two have been together ever since.

On to awkward moments on air: As "Fixer Upper" fans will no doubt know, Chip Gaines has quite the penchant for performing stunts. Unfortunately for Chip, however, things haven't always panned out all that well for him (and we're not just talking about the time he swung from a stair opening straight into a camera, crotch first).

For one, there was the time he decided to take advantage of a wall being taken down and embrace his inner Chuck Norris. Chip did his best impression of the action star, flying through the wall, and we have to say we were impressed. However, his landing wasn't what we'd term "graceful," and after a brief moment of grimacing on the floor, his wife asked, "Chip, did you just break your stupid arm?" Ultimately, he shook it off, and Joanna Gaines quickly congratulated him, cheering, "You should be a stunt double!"

Perhaps Joanna should have gone slightly less hard on the enthusiasm, because Chip would continue to try his hand at stunt work in the years that followed — and in an episode of "Fixer Upper: Welcome Home," she pointed out that some of her husband's antics weren't always clearly thought through. Case in point: stilt walking. "Any project Chip is in, it's like there's something in the air that makes him want to do something really stupid," Joanna narrated as he stumbled around on the stilts. Sure enough, Chip acknowledged that he had bad ankles ... shortly before collapsing in front of his wife. Thankfully, there weren't any real injuries, and the couple quickly dissolved into a fit of giggles.

Pivoting to an awkward moment Chip Gaines and Joanna Gaines had at a Hollywood hangout, some may be surprised to know the HGTV couple had a super embarrassing moment with Taylor Swift at the 2019 Time 100 Gala. 

Speaking about their cringeworthy moment with the pop star in a 2023 episode of "The Tonight Show Starring Jimmy Fallon," Chip explained that they had thought they'd made the list of 100 influential people in their region. As such, they were already surprised to be in the same room as someone like Dwayne "The Rock" Johnson. However, things ramped up several notches when, as Chip recalled, "You're sitting next to The Rock, and you see him gasp about this amazing creature. ... We were just like, 'Who in the world? Who? Who came in?'" Of course, it was Swift, who then made eye contact with the couple and made a heart sign with her hands. Suffice it to say, the couple didn't quite know how to act. "We thought it's, for sure, someone behind us ... like idiots," Joanna recounted, the twosome both looking over their shoulders to demonstrate their reaction. 

Unfortunately for the Gaineses, the awkwardness didn't stop there, and despite both of them reminding Fallon that he had been with them on that night, it took several minutes for him to recall any of it. Chip made light of that, though, chirping, "Whenever Timberlake says something, you know exactly what he's talking about. But if I mention some bro moment, you have no idea what I'm talking about." Fallon ultimately did seem to remember the evening, but Chip poked fun of that as well, chiming sarcastically, "Oh, of course, like it was yesterday."

By the time Chip Gaines and Joanna Gaines joked about their mishap with Taylor Swift on "The Tonight Show Starring Jimmy Fallon," they were fairly seasoned at talk show appearances. However, in 2018, that was not the case — and Chip didn't exactly hide the fact that he felt a little out of his depth. Far from it, while Fallon was introducing the couple, Chip started pointing to the show's band, The Roots, prompting Joanna to laugh, "He's so nervous." 

In fairness to Chip, he wasn't the only one with some jitters. Joanna also had a slightly awkward live interview moment, sharing, "I'm touching your desk. ... I've always wanted to touch the desk." Cue Chip, also leaning across to touch the desk, prompting Fallon to laugh, "Oh, stop it, please. It's a normal desk." Chip then nicked a Sharpie on Fallon's desk, after which the talk show host began offering up other souvenirs. Joanna laughed along, joking that she would be leaving with a mug ... though evidently, a tissue box was a step too far. "Chip, stop," she scolded, taking the box away from him as he tried to hide it in his blazer. 

The awkwardness didn't end with that, either, because Chip began jumping up for applause at random. Luckily, his antics were thoroughly enjoyed by the audience, which Chip very un-subtly pointed out to his wife. "Babe, they love us," he quipped. A few more jumps up for applause later (one of which saw Joanna whack him on the leg, and two of which saw even Fallon begging him to sit), the host joked that they would nonetheless be invited back on the show. If ever there was a couple who exemplified "all's well that ends well," it'd be these two.