20 Years of Survivor

The 20 Most Hilariously Awkward Survivor Moments

A whole lotta cringe…

Photo: CBS

In celebration of Survivor’s 20th anniversary, over the next couple of months, Inside Survivor is publishing a series of articles looking back at the show’s history, best moments, and most memorable characters. 

Survivor can be a lot of things—emotional, shocking, thrilling. It can also be toe-curlingly cringey at times. You know, those moments where you want to just dig a hole—not unlike Rupert’s underground shelter—and bury yourself in it? The kind of moments that turn your face beet red out of second-hand embarrassment. And yet, they can also be side-splittingly funny. 

Seriously, there have been so many hilariously awkward Survivor moments over the years that I could have made a top hundred list. Narrowing them down to a top twenty was extremely tough, and I’m sure I’m missing some absolute cringe-worthy classics. Also, it should be noted that I’ve tried to keep things light—I avoided genuinely uncomfortable moments like the Varner/Zeke situation and Brandon’s meltdown.

20. Angie Wants Cookies (Philippines)

Matsing was a hot mess of a tribe, and let’s face it, cookies could probably have been more useful than Russell Swan. Still, that doesn’t make Angie’s answer to Jeff’s, “What’s one thing you wish you could change about this tribe?” any less awkward. What’s even funnier is Malcolm hopelessly trying to defend Angie’s answer, as if it’s not one of the most ridiculous things he’s ever heard. 

19. Shane’s Red Testicles (Panama)

I could have made an entire list of awkward moments just from Panama alone. But this particular scene has a bit of everything—embarrassment, public nudity, and hilarious commentary. Cirie diagnosing Shane’s chafed testicles through tears of laughter is just straight-up television gold. “Shane’s like a cartoon character,” comments Cirie. “And now he’s a nude cartoon character.” 

18. “Sister, Sister!” (Philippines)

Survivor loved ones visits are a cornucopia of cringe, and this small moment of Lisa reuniting with her brother Justice in Philippines is a prime example. “Sister, sister…” Justice exclaims as if he’s a character in a bad soap-opera delivering relationship exposition. Maybe he was just trying to keep his famous sister’s identity secret in case she hadn’t told everyone her real name? Still, though, you can’t deny the facts (of life) that it was awkward as hell. 

17. Heidi Wants A Different Answer (The Amazon)

Who deserved to win The Amazon? If you didn’t say “Heidi,” then I’m going to need you to think about it properly and answer again. Heidi desperately trying to get Jenna and Matt to tell her she deserves to be sitting in the final two is hard to watch… but so damn funny. “Is that the only person?” she asks after both finalists say Rob deserves the spot. “I think they covered it,” Probst interjects as the rest of the jury watch through their fingers.

16. Brian’s “Foxy Wife” Sends A Video (Thailand)

I don’t know what is more awkward in Brian’s video from home scene. Is it the MTV Cribs-style tour through his mansion-sized house, complete with a grand piano and a garage full of new cars? Is it his wife doing a sexy dance and Clay visibly salivating over her? Or is it Brian’s snide remarks about his own wife (“Why don’t you clean up?”)? It’s like something from a lost episode of The Office

15. Rupert’s Waterlogged Cabin (All-Stars)

“Digging into the sand is the dumbest idea I’ve ever had in my life,” says Rupert after a storm turns his makeshift shelter into an outdoor swimming pool. And that’s coming from a guy who unashamedly wears tie-dye on national television. “It’s now underwater; we are homeless.” The process of building the structure is awkward enough, but the appraisal from shelter-expert Rafa tips it into comedic brilliance. The look of confusion and disgust on this man’s face as Rupert tries to explain the shelter’s guttering system is pure hilarity. 

14. Amanda And Danielle Fight For A Clue (Heroes vs. Villains)

Spare a thought for the curator working at the Robert Louis Stevenson museum the day Survivor paid a visit. One minute your presenting literature exhibitions, the next minute, there are two women in their underwear fighting over a scrap of paper while a man sits on a bed eating a bowl of popcorn. Awkward doesn’t even do it justice—and I’m not talking about Lisa Whelchel’s brother. And all poor Colby wanted to do was just watch Treasure Island in peace. 

13. Jeff’s Invasive Reunion Show (China)

Survivor reunion shows are another hot-bed for awkwardness, but Jeff was on rare form at the China reunion. Firstly, he pries into Jamie and Eric’s dating life and asks if Eric is still a virgin, like a jock teasing a nerd in high school. Then, he asks Courtney if she has an eating disorder before informing everyone that she actually weighs more now than when she started the show. “Jeff Probst just called me fat,” Courtney quips. “I could have phrased that better,” Jeff admits. 

12. Kathy Pees On John (Marquesas)

“I need somebody who can pee on my hand!” is one of the weirder requests heard on Survivor, or at least a close tie with Angie’s wish for cookies. I talked in the greatest duos list about those instantly iconic Survivor images, well, Kathy squatting over John’s hand as she pees on his sea urchin sting is definitely one. What makes it even funnier is how Paschal gets camera shy and can’t go in the moment. “Finally, when I was pulling up my pants, I got very embarrassed,” says Kathy sounding like she just had a regretful, drunken one night stand. 

11. JT Writes Russell A Letter (Heroes vs. Villains)

From JT’s perspective, I can understand his gambit to send a note to Russell, offering him his idol. From the audience’s point of view, knowing all the facts, it’s hard not to feel second-hand embarrassment as he pens this heartfelt letter to the enemy. And it only gets more cringe-tastic as Parvati and Russell mockingly read the letter aloud like a couple of bullies who just found their friend’s secret childhood diary. XoXo. 

10. Becky And Sundra Try To Make Fire (Cook Islands)

Do we truly know if Becky and Sundra ever stopped trying to make fire? Seriously, this fire-making challenge should be in the Guinness Book of World Records. It’s like one of those long-winded jokes that start funny then get repetitive then come all the way back round to funny again because it’s so ridiculous. The challenge goes so long that they run out of flint, and Jeff has to give them matches! And it still goes on for what seems like another hour! And Sundra runs out of matches! 

9. Adam’s Podium Idol (Winners At War) / Randy Plays Fake Idol (Gabon)

Yes, I’ve cheated and shoved two entries into one. I couldn’t pick one over the other, and they are enough similarities that it makes sense to combine them. 

We’d seen fake idols before Gabon, Yau-Man started the trend, Ozzy one-upped it with his carved stick, but it was Bob that really perfected the art of the fake idol. Bob’s trinket is so convincing that it completely snows Randy (at least if you believe the edit) into playing it at Tribal. All the while, his tribemates struggle to hold in their laughter. It’s actually kind of cruel—but undeniably awkward.

Adam’s blunder is less mean-spirited, as it’s a gambit he takes on his own, hoping the fleur de lis within Jeff’s podium is an idol. It only becomes cringey the more Jeff encourages Adam to keep going, leading to the podium itself being played as an idol. Spoiler alert: it wasn’t an idol. 

8. Russell Offers To Buy Natalie’s Title (Samoa)

Desperation is never a good look, especially not when you’re on live television wearing a fedora and guyliner. Russell offering Natalie $10,000 to give him the title of Sole Survivor at the Samoa reunion is so butt-clenchingly awkward. “I want it on paper, written down, that I am the Sole Survivor,” he begs as a bemused Natalie looks on. “I’m not interested,” Natalie responds. “In order to be Sole Survivor, you need to get the majority of the votes from the jury.” I couldn’t have said it any better myself.

7. Greg’s Sister (Borneo)

As I mentioned earlier, Survivor loved ones provide some of the best awkward moments, and still, to this day, Greg’s home video from his sister sits in a class of its own. The coochy coos and kissing noises and mimed humping, it’s a psychiatrist’s wet dream. “At least we know he’s not the only screwball in his family, maybe it’s a genetic trait over there,” says Sean in confessional.

Then Greg makes it even weirder in his video back to her. “We feel like we could feel you, and we felt you, some of us felt you, and others just imagined what it’s like to feel you,” he says, leading to an all-time classic Rudy confessional. “It sounded like Greg was talking maybe… incest, that’s the way it sounded to me.” Even funnier is Rudy’s recorded message, “We gotta put up with this for about two more weeks, then we might kill him, is that doing you a favor?”

Of course, Greg knew he was pushing buttons, that’s just what Greg liked to do. “Sexual allusions towards my sister? WHAT’S GOING TO HAPPEN?!” That doesn’t stop it from being hilariously uncomfortable.  

6. David Murphy’s Proposal (Redemption Island)

At the All-Stars reunion, Boston Rob dropped to his knee and proposed to Amber. It was a beautiful moment of happiness serenaded with the applause of a jam-packed Madison Square Garden. Seven years later, Boston Rob is in attendance for another Survivor proposal, as his Redemption Island castmate David Murphy surprises his girlfriend, Tocantins castaway, Carolina. This is not a beautiful moment of happiness.

Everything about this is shuddersome. The pre-proposal patter between David and Jeff is stilted and strange. Then the proposal itself, oh lord. Firstly, Carolina does NOT look happy. She’s only been dating David for a few months. At one point, she even tells him to “shut it down, right now.” That’s when she’s not burying her face in her hands out of embarrassment. The poor woman has nowhere to hide as all the cameras point at her. Just to add to the awkward hilarity, Amber is sitting in the seat in front and turns to stare as Carolina rapidly thinks, ‘how do I get out of this?’ She can’t. She has to say yes. “Yes, oh my god, yes… oh god.” 

Spoiler alert: They never got married and broke up a few months later.

Somehow, David found a way to out awkward anything that happened on the season. And this season featured Phillip Sheppard! 

5. Neleh’s Half-Eaten Mint (Marquesas)

Ther have been plenty of awkward moments revolving around food on Survivor. Banana etiquette, anyone? But Neleh’s post-reward offering in Marquesas takes the cake, or, should I say, takes the half-sucked mint candy? Even the lead-up to it is cringe-inducing, as Neleh goes into great detail of all the reward perks, including the array of food and how she scrubbed herself silly with a loofah. 

“The only thing I have left to share is this mint that I shoved in my mouth really fast, so if everyone wants to take a little nibble,” she tells her hungry tribemates. “You’re offering seven starving adults a piece of candy out of your mouth,” Sean comments in confessional. “Keep your mint candy, man. That’s like saying, ‘Anyone want this piece of doo-doo?'”

It’s seriously one of those scenes that I have to watch with gritted teeth every time I see it. Like, maybe this time she won’t offer the tribe a half-eaten mint from her mouth…? Oh, no, she did, I didn’t just imagine it.

4. Coach’s Amazing Amazon Adventure (Tocantins)

Much like with Panama, I could write a whole list solely comprised of Coach moments. Trying to pick just one was difficult. It could have been his Exile epic, his many denied hugs, his assistant coach, and so on. But it felt the most right picking one of the classic Coach stories, specifically, his near-death experience in The Amazon. 

The story itself is incredible, there is a drop-off by military helicopter, an 18-foot kayak, being captured by four-foot tribesmen with bow-and-arrows. It’s like the synopsis of the next Dwayne “The Rock” Johnson movie. But it’s the silent reactions from his fellow tribemates that up the awkward factor. Eventually, the silence is broken by the most important question from a confused Brendan, “How much does it cost to get a military copter to drop you in?” That would be “free,” obviously. “I believe Coach once went kayaking,” comments Stephen, “that part is definitely true for sure.”

It gets even wilder at Tribal Council when the group brings up the story, and Coach reveals he was holding back! “I try to tone it down because if I told them the tribe was looking in my ass and talking about eating my ass…” he says. “When I tell these stories, I try to give them the PG-13 version.” 

The craziest part about all this, though? Coach DID have many kayak adventures, the LA Times even wrote about them, and so, could, maybe, just maybe, the Amazon story be true? I sure hope so. 

3. “Natalie, can I have your jacket?” (David vs. Goliath)

From our 2018 Funniest Moment write-up: “Not since Holly Hoffman filled Dan Lembo’s $1600 alligator shoes with sand has an item of clothing caused so much drama on Survivor. Jacket-Gate was the perfect comedy of errors. Angelina wanted to vote out Lyrsa, but she also wanted her “Members Only” jacket, and so, she sent Natalie to do her bidding like some sort of cartoon henchman. 

The failed jacket heist became a major topic of conversation at Tribal Council, with Angelina deflecting and Natalie hilariously repeating the refrain “I’m in sales,” as if that was a valid defense of her actions. In the end, Natalie had her torch snuffed, and Angelina’s pleas for warm clothing echoed into the night. The moment was so iconic that Lyrsa commemorated it by having it tattooed on her arm.”

2. “It’s A F***ing Stick!” (Micronesia)

“Don’t worry, baby,”—the immortal last words before monumental humiliation. It’s an all-time classic Survivor moment that builds beautifully to an iconic punchline. Seriously, outside of Jeff’s catchphrases, “it’s a f***ing stick” might be the most memorable quote in Survivor history. Every time I watch Jason’s world crumbling before his eyes, I cringe on his behalf, as Eliza tells him point-blank, THIS IS NOT THE IDOL! 

What makes it so funny is that it’s not even a convincing fake. It’s not like Bob’s idol, where you could understand why Randy might believe it’s genuine. It is literally a stick with a smiley face carved into it. And yet Jason just gullibly accepts it with no second thought. He proudly tells Eliza about it, and she’s so excited to have found a saving grace, only to look in her bag and find this toddler’s arts-and-craft reject. Even when Eliza tells him there is no way it’s real, Jason still desperately clings onto the belief. “It has a face on it, don’t worry,” he says as if that is encouraging in any way. 

1. Billy Falls In Love (Cook Islands)

We’ve all had a crush on someone before. We’ve all probably misread romantic signals at one time or another. Luckily, for the majority of us, those things don’t happen on a prime-time TV show. But god bless Billy for giving us this moment that will forever live in Survivor infamy. Of all the hilariously awkward Survivor moments, this is the one that always comes to mind first above all else. 

Candice just wanted to offer a worried Billy her tribe’s support. But suddenly, her platonic “we love you” got filtered through Billy’s mind into a declaration of everlasting love. However, it isn’t Billy’s heartfelt, “I love you too,” that is the most awkward part of all this. It’s his speech at Tribal Council about finding something more important than the million dollars. “My prize was that I fell in love in this game, love at first sight, her name is Candice,” he says in complete earnestness. 

Probst’s wide-eyed, leg slapping reaction is glorious, as are the stunned faces and eye-rolls from the rest of the tribe. “I want to be respectful, but what would she base feeling the same way you feel on?” asks a perplexed Jeff. Err, haven’t you seen that fetching skull-covered t-shirt he’s wearing, Probst?! What lady wouldn’t be swooning at such a finely dressed young gentlemen? Sadly, much like Carolina and David, the feelings only went one way. Billy and Candice did not sail off into the sunset and live happily ever after, but they will always have this awkward moment in the sun. 

Honorable Mentions: Colby & his mom (The Australian Outback), Sean rides a horse (Thailand), Erik licks chocolate off Cirie’s fingers (Micronesia), JP is strip-searched (HvHvH), Vince hugs Jenn (Worlds Apart), Vytas does yoga (Cambodia). 

Stay tuned to Inside Survivor for more 20 Years of Survivor content over the coming weeks.

Written by

Martin Holmes

Martin is a freelance writer from England. He’s represented by Berlin Associates for comedy writing and writes about TV and entertainment, currently for TV Insider and Vulture, previously Digital Spy, ET Canada, and Yahoo. A finalist for the Shortlist Sitcom Search in 2012 for “Siblings,” Martin received his BA in English with Creative Writing from The University of Hull. Martin is the owner and editor-in-chief of Insider Survivor.

6 responses to “The 20 Most Hilariously Awkward Survivor Moments”

  1. Next time, please include video clips instead of photos so we can all relive these moments.

  2. Hi Martin, in your honorable mentions here, I believe it was JP who was strip searched in HvHvH. Great article, thanks for posting!

  3. Others worthy of mention:

    Jerri fantasizes about ‘aint no Hershey bar’ Colby
    Grindgate – Thailand
    Rich rubs Sue with his junk – All Stars
    Brandon Hantz melts down – Caramoan

    • He said he wouldn’t be including genuinely uncomfortable moments, so I don’t think that your last 3 were in the running. They were definitely all awkward and cringe-worthy though.

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