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Kim and Penn Holderness Reveal How They Became The Amazing Race's Oldest Ever Winners

Well, they are Gen X. YouTube sensations Kim and Penn Holderness detailed to E! News how they used their map-reading and communication skills to best The Amazing Race competition.

By Sarah Grossbart Mar 04, 2022 11:00 AMTags

Before The Amazing Race champs Kim and Penn Holderness traversed 17 cities in seven countries or even stepped foot on the starting mat in London's Trafalgar Square, they hit the bar. 

"Kim made me go to a map-reading class," Penn told E! News hours after their victorious run aired on the CBS series March 2. "It was at a brewery! It was awesome." And while the REI-hosted session gave them some helpful tips about identifying midway markers and backstops to keep them from going too far, mostly, he said, "A lot of it just came back to us because we're old and we used maps."

Still, the choice to do a brush-up—just a small part of the extensive preparation the YouTube personalities underwent after getting cast on the reality competition's 33rd season—proved particularly wise when they returned from the show's longest pitstop ever and learned that a significant uptick in self-driving was among the many COVID-era protocols put into place.

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How The Amazing Race Returned During COVID

"Eight of the 11 legs, we had to drive ourselves," noted Kim, 45. "And I don't care what anybody says, if you're navigating and driving in a foreign country without GPS, it is panic-inducing. And you could find your way to a spot and they could ask you to tie your shoes and it's going to seem impossible."

Navigation was a particular "strength of ours," she acknowledged. "We always got places first, and it was still just, like, our armpits were sweating the whole time. It was so terrible." Joked Penn, 47, "I'm sweating thinking about it right now." 

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Their proficiency with maps and early-'90s-era MapQuest-style directions gleaned from their days working as local news reporters in Florida and Colorado ("All we did all day was sit in a car with somebody else with a map trying to figure out where to go," recalled Penn) was just one way they used their Gen X status to their advantage en route to becoming the show's oldest winners yet.  

Already fans since the Emmy-amassing series' 2001 debut, the couple went back and rewatched every episode, this time with pens in hand. "We took notes on what decisions people made leading to them to win and leading them to get eliminated," said Kim. Added Penn, "We had spreadsheets on every final episode about the breakdown between roadblocks and route infos."

But one of their more crucial choices was made long before casting directors reached out to the family that's been garnering upwards of a billion views on YouTube and Facebook since their 2013 release "XMAS Jammies," a parody of Will Smith's "Miami" meant to be their digital Christmas card with daughter Lola, now 15, and son Penn Charles, now 12. 

"The best accidental preparation that we did was going to marriage counseling," said Penn of the therapy they used as research for their book, Everybody Fights: So Why Not Get Better At It? Agreed Kim, "That counseling was probably the best training for this experience."

As a result, they were one of just a handful of teams to make it all the way through the famed race around the world without arguing. "It escalated," acknowledged Penn, pointing to a particularly confusing drive through Greece that saw him proclaim, "Okay, I'm going to let Jesus take the wheel. And for right now Jesus is Kim." (As he joked, "I likened you to Jesus. It was a compliment.") 

And then there was that final memory challenge that had Penn questioning if his wife could truly recall the boat she had ridden in while in Portugal. "He kept second-guessing," she griped, before joking, "We're in a fight right now!"

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In the end, though, Kim's insistence that he trust her pages of meticulous notes (plus all those hours the triathletes spent running with backpacks or while holding random, oddly-shaped objects) helped propel them past flight attendants Raquel Moore, 31, and Cayla Platt, 30, and pals Ryan Ferguson, 37, and Dusty Harris, 38, on that final leg in Los Angeles. 

"Everyone was so young and so fit and so strong," Penn said of their initial impression. "And we considered ourselves to be young, fit and strong until we met these other people. And so we looked it up and we're like, 'Oh yeah! Old people don't really win this race very often because it can be a real limiting factor when it comes to the physical toils of getting around in a backpack.' There's a lot more walking and climbing and running than this show has time to show the viewer."

The actual process was "grueling," he continued. "And it was one of the reasons we trained pretty hard physically for the race to get through that and then hope that some of the wisdom that comes with age would actually be an advantage." 

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Of course, nothing could have prepared them for the detour they'd undergo just three legs in. 

The couple, nicknamed "Mom and Dad" by their competitors "because we sit and we watch BBC and we're like, 'What's going on in the world? How's Brexit?'" explained Penn, had, indeed, been tuning into the local news' COVID coverage during their early legs in the United Kingdom. "The fan was on and something was hitting it," he said. "We could tell."

Seconded Kim, "I immediately said, 'We're not going anywhere. We're not finishing this race.'" 

It was a feeling that solidified days later once they made it home to Raleigh, N.C.—after production scrambled to get host Phil Keoghan and show co-creator Bertram van Munster back from the Arctic Circle and the hundreds working on the show safely to the States.

"We landed expecting, like, 'Are they going to test us?' And nobody was even talking about it," recalled Kim of that strange late February 2020 stretch. "There were people on TV calling COVID a hoax. I was like, 'You guys! It's coming!'" 

So when producers reached out about the late 2021 restart, "Our initial reaction was no," shared Penn. "It didn't seem like a responsible, safe way to do things."

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But as they learned about the comprehensive plan being put in place ("Low transmission countries, low transmission areas, proof of vaccination at every point, anyone you came into contact with was already pre-cleared, testing every 48 hours, quarantining in between," detailed Penn) and realized how much they wanted to show their kids the importance of finishing what you begin, they were pulled back to the restart line in Zurich, Switzerland.

Their kids were, after all, the ones who'd urged them to throw on their backpacks in the first place. "Our children, said, 'What are you going to remember? Some random February or the time you went on The Amazing Race?'" recalled Penn. "And they kind of theoretically and literally pushed us out the door."

Plus, it helped that they'd long since formed "this, like, trauma bond," with their fellow racers, noted Kim. "You're like, 'Where were you when the pandemic started?' And we were in Scotland with these people on this game show." Two years in, they're still in constant contact with the entire squad. "I think that's one of the biggest surprises out of this experience for me is that I would come away with real, true friendships," she said. "I love these people."

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And that's who was by their side when the finale aired, fifth place finishers and radio hosts Lulu and Lala Gonzalez having planned a no-detail-left-ignored watch party in Miami, complete with Amazing Race-style clues about each upcoming activity. 

Though, admittedly, Kim and Penn missed the last few minutes of the episode because they were so trained on their kids' reactions to watching them race through the tunnel at California's Dignity Health Sports Park and onto the final mat. 

"Like, a 15-year-old actually being excited about their parents and thinking that they're cool?" joked Penn. "That is the biggest gift there is."

Of course, the duo have a bit more largesse in mind.

While "Uncle Sam is going to get his cut" of the $1 million prize, Kim noted, and a hefty chunk will be set aside for two college educations and "putting some stuff away for aging parents," she said, "we have some plans to share. So that we are going to be talking about real soon." 

Well, the world is waiting...