Top 10 Weirdest Challenge Hookups

Sometimes on the Challenge you have the hookups and showmances that make sense immediately. For example: Dario Medrano and Ashley Kelsey began what would become a year-long relationship on Invasion of the Champions. The two wallpaper characters just made so much sense together that you’d have expected to them to have met hanging up in the aisles of Home Depot. Then you have the showmances and hookups that make you go “what?” My focus will be on the “what(s)?” This list breaks down the top 10 weirdest hookups and showmances that were on the Challenge.

The great part about this list is there is definitely more that I am missing. I am honestly more excited to read in the comments which I’m missing so I can fondly remember them.

10 CT and Anastasia — Rivals 2

The funniest thing about this hookup is Anastasia’s confessionals through the first two episodes. They make you wonder if Anastasia had ever watched an episode of the show before. She was seemingly unaware of CT and Diem’s almost decade long history, and I guess she thought CT was just a quirky guy. Regardless, they banged in the Thai jungle and throughout the house.

In the end, Anastasia ended her fling with CT by mauling him in the house before getting eliminated in the jungle the following night. I wonder if CT would even remember her name if shown her photo.

9 Sarah and Alton — Battle of the Seasons

The Sarah and Alton mini showmance is weird because it’s almost like a fun fact. When you think about the two competitors and the time periods they competed in, you are almost surprised to see that they appeared on a season together, let alone had a bit of a fling.

At Challenge Mania live in Los Angeles, Alton revealed one of the reasons he and Sarah bonded was because they both woke up early and would clean the house/wash the dishes.

8 Nany and Marlon — Rivals 2

Nany and Marlon are two beautiful, sexually active people. However, when people think of Marlon’s sexual exploits on Rivals 2, they remember him and Derek hooking up in the first episode and it being revealed later. Likewise, when you think of Nany and all her hookups, so many people come to mind that Marlon gets lost in the mix, including Bananas, Hunter, Cohutta, Johnny Reilly, Adam Royer (RW), Heather Marter (RW), and heavily rumored CT.

These two had no relationship storyline after their one episode fling either! It’s such a throwaway showmance in the big picture.

Sidenote: Nany is kind of into short/average height men (not Marlon).

7 Big Easy and Devyn — Battle of the Seasons

The visual of Big Easy and Devyn was funky. The pageant queen and future Television host paired with the crude party-guy Big Easy. You ever hear someone tell you that your aura has a certain color? Big Easy’s Aura is a McDonald’s red, and you can see it from a mile away. How is that relevant to the article? It isn’t, but I’ve been waiting all week to use that line.

On Battle of the Seasons, Big Easy made his sixth Challenge appearance and Devyn was on her rookie season. The two bonded as they both were able to have normal conversations among a house of children and crazy people. Big Easy actually comes from wealth as his family was apparently successful pig farmers. He actually runs a very successful travel agency that focuses on Spring Break related parties. However, once these two got outside of a Challenge house, they quickly realized that being able to have regular conversation doesn’t mean you’re actually in love with each other. Devyn is all over the place, working on the Wendy Williams show, being a dating coach, getting married herself, and everything in-between.

This duo’s time on the Challenge was ended in the most extreme of ways when facing off against one another in elimination where Big Easy famously quit, enraging Camila and TJ. Devyn was there to console him after the elimination was over.

6 Landon and Tonya — Inferno 2

Wait, what? When people think of Landon, they think of the guy who was a competitive beast and a genuinely nice guy. On a spiciness level, Landon is about a 2 out of 10. Meanwhile, Tonya was problematic to say the least, and she had a spiciness level where you’d have to sign a waiver in order for the restaurant to be able to serve you a dish of Tonya.

Well, on the Inferno 2, after a drunken night, Landon found himself in bed with Tonya. Which, I do not blame him, Tonya had an amazing body. However, you could tell that Landon immediately regretted it the next night. Landon lost his Challenge virginity and didn’t even remember it. It is such a weird hookup in the bigger picture of Landon and Tonya’s dramatically different Challenge careers.

5 Paula and Mike — Rivals 1

Part of me thinks Paula was bored when she decided to make Mike Ross her showmance on Rivals 1. Paula had her fair share of hookups, so by the time she was on her eight season of the Challenge, she either had been there before or knew she had no interest in certain people. After having a deeply enigmatic relationship where she was often way more into Dunbar than he was into her, Paula saw a cute little puppy named Mike Mike and decided to take him for a ride.

Honestly, Mike Ross lived the dream of every single Challenge fan. He woke up, got on a plane, competed in daily challenges where he performed well most days, got to party with the cast members, got into a fight with other cast members, hooked up, and made it to the final. The Rivals 1 final is one of the hardest in Challenge history, and the fact Mike got through 95% of it is fucking nuts in retrospect. I’m glad he never came back so we only remember him positively. Paula would go on to have another weird hookup the following season, Ty, while she had a boyfriend at home.

4 Evelyn and Brooke — Gauntlet 3

The best part about the Evelyn and Brooke showmance from Gauntlet 3 is that the feelings are not mutual. Evelyn is gaga over Brooke, while Brooke sort of tells Evelyn that she is not into women, and would prefer Evelyn if she had a penis. It was weird as hell. Especially after Brooke got eliminated and Evelyn was in tears. Coral’s commentary on the situation where she mentions “I don’t even think she’s really a lesbian.”

At the reunion, even Evelyn is at terms with that fact. Yet, they were so into each other until they weren’t. I wish Brooke was decent at the Challenge because she was reality TV gold.

3 Tony and Ashley — Rivals 3

This is another hookup where when you see it, you’re like, wait, when did this happen? On Rivals 3, Ashley chose to spend her early days in the game hooking up with Jamie. They banged in the shower where the entire house watched. Ashley cared about Jamie enough to have a hysterical breakdown about him potentially making out with Nicole Ramos. She also fat shamed him, because that encapsulates the Ashley Mitchell experience.

Tony came on after recovering from a ruptured spleen and chose to spend his time in bed with Jessica Mccain. Not sure if he and Jess did anything more than make-out as Jess famously made a burly 6'4 dude sleep on a small couch during Real World Portland. Regardless, following Jessica’s elimination loss, Ashley made a move into Tony’s bed. They played it off as nothing more than kissing, but is quite clear in the video that undergarments, and I’m not a doctor, but something more happened there.

Ironically, Ashley has gone on to live Tony’s dream. She is a 2x Challenge Champion, has won over a million dollars, and is one of the faces of the franchise.

2 Jay and Jonna — Exes 2

Jay has at the very least made out with Jenna, Jemmye, Jessica, and Jonna. So many dudes hate Jay because of the way he quit the Exes 2 final, and they definitely hate him more knowing that he has hooked up with so many reality television girls. His relationship with Jonna was a circumstance where they saw their two exes hooking up, and decided, well “let’s get back at them.” I’d honestly argue that Jay was the biggest winner in this equation. He had no leverage, and now he had the beautiful Jonna (who even though Zach was awful, still had trace feelings for him).

Everyone watching the show at home simply had a perplexed “why?” look on their faces any time these two interacted. They had no chemistry, did not look cute together, and Jonna probably regretted it when all was said and done.

1 Tyrie and Jasmine — Rivals 1

There is so much to unpack with the showmance of Tyrie and Jasmine. For starters, Jasmine had a boyfriend at home. Within a day or two of being on the show, she is grinding up on and making out with Tyrie. Despite her doing confessionals about wanting to be faithful, she is now all-in with Tyrie.

Second, they hookup, and in order to hookup, Tyrie takes a couple of Tyler’s XL condoms. Good for Tyler and Tyrie. However, if they wanted to keep it on the DL, taking someone’s condoms is not the way. I also think Tyler mentioned that XL condoms were expensive, which they’re not really, it’s just that they’re sparse, and probably hard to come by when in a Challenge house (unless production gives them condoms).

Third, after hooking up, Jasmine refers to Tyrie as a big brother. That’s super fucking weird. Also, the size difference was amazing to watch. Jasmine was like 90 lbs, while Tyrie was built like a line-man.

These two would go on to carry the entertainment of Exes 1 by being a hilariously dysfunctional pair. Their fight in the second episode is one of my favorites. Tyrie yelling “oh damn Tyrie got sent home the first week, not like that’s ever happened before!” is one of my favorite moments in Challenge history as the self-awareness level is through the roof. Jasmine recently got married, while Tyrie has gotten in great shape and is a personal trainer for Equinox.