12 Most Memorable Romances In The History Of The Challenge

In the immortal words of Johnny "Bananas" Devenanzio: "All is fair in love, war, and challenges." 

"The Challenge" is MTV's longest-running series which sees individuals face off in a "grueling physical and mental" competition at their chance to win prize money and the bragging rights that come along with being a "Challenge" champion. In a game that can be compared to no other, the challengers are made up of multi-dimensional athletes who need to have the ability to strategize on the fly.

When the contestants aren't falling from 20 feet in the air or eating live cockroaches, much of the game is actually played within the confines of the "Challenge" house. Amidst the bruises, the politics, and the drama of "The Challenge," new romances can bloom ... or should we say showmances. Whether it's a case of true love or simply just "polidicking," every move you make affects your outcome in the game ... and usually not in a good way. Over the nearly 40 seasons and multiple spin-offs, there are a ton of iconic "Challenge" relationships that fans will never forget. Read on for our list of the most memorable romances in the history of "The Challenge."

"The Challenge" has featured many memorable relationships over its long history, but nothing will ever top the heart-wrenching love story between CT and Diem Brown. Although Chris Tamburello is technically behind Johnny Bananas in total challenge wins, he arguably remains the most iconic and well-rounded player in the history of "The Challenge." Not only is he a beast at physical, mental, and eating challenges, but he also managed to find true love in the franchise.

The relationship kicked off during Season 13, "The Duel." Diem had previously been diagnosed with ovarian cancer and was grappling with hair loss from chemotherapy. She wore wigs for the first few episodes of this season, and CT was one of the first people to make her feel beautiful without hair, calling her "GI Jane, lookin' like a little sexy supermodel secret agent." Despite fans always rooting for these two, they had an on-again off-again relationship for years, but never stopped caring for each other.

During "Battle of the Exes II," they were paired together and managed to rekindle their close friendship. "Having a partner like CT with me gives me some sort of weird relief that somebody is in my corner ⁠— and that feels comforting," Diem said. However, soon after the season began, Diem was medically disqualified due to health complications, and CT left the season to be by her side. Only a few short weeks later, on November 14, 2014, Diem passed away (via People). Thankfully, CT was able to see her in her final days, proving their love really was life-changing.

Tori Deal entered her rookie season, "Dirty Thirty," with her then-boyfriend, Derrick. However, Derrick was soon eliminated, and Tori had to continue the remainder of the season without him, making it all the way through the final. Despite their infatuation and their plans to start a family together during the beginning of the season, Tori began to grow closer to Jordan Wiseley after Derrick's departure, with Tori calling Derrick to break up the moment the season ended. Although they both deny any cross-over during filming, Derrick still vehemently maintains that she cheated on him with Jordan.

Despite their rocky start, Jordan and Tori went on to have a very public, years-long relationship. Tori even posted YouTube videos about their journey of moving in together. Only a few years later, during "War of the Worlds 2," Jordan left fans speechless when he got down on one knee and proposed to Tori following an elimination win. Unfortunately, in late 2020, they each took to Instagram to announce the end of their engagement, with Jordan sharing that his time with Tori was the "best and most beautiful time" of his life. On the "Chicks in the Office" podcast, Tori shared that COVID-19 was "really hard" on them and caused them to fight constantly, leading to the breakup. As filming for Season 38 has just recently come to an end, there have been rumors swirling about a possible reconciliation between the two — but only time will tell.

Some pretty interesting characters have graced "The Challenge," but Abram Boise is undoubtedly one of the most explosive contestants the series has ever seen. Cara Maria Sorbello and Abram's relationship began when they met in 2010, during Season 20, "Cutthroat," but it was anything but smooth sailing. The couple spent years in a toxic on-again off-again relationship, sharing many aggressive public fights.

Abram once compared Cara Maria to a cat, saying, "When you try to chase a cat it just runs away and then you turn around and go sit down and the cat shows back up at your leg" (via Us Weekly). However, in one of the most legendary moments in "Challenge" history, Cara Maria got frisky with Thomas Buell in the hopes of using him for political reasons during "Battle of the Bloodlines." In an unforgettable twist, Abram then showed up to participate on the season, bringing with him an uncomfortable amount of tension in the house, ultimately leading to their final breakup.

When asked about their turbulent relationship, Cara Maria shared, "He's so passionate and so intense that sometimes you just need to get away" (via Us Weekly). In fact, the word "passion" is one they've used often to describe their volatile relationship. "Any public fights or anything along those lines, any of the wild things, those are all things that have erupted from an enormous amount of passion between the two of us," Abram said in an interview with Ifelicious.

Cara Maria has had many memorable relationships during her time on reality television. But arguably, the most iconic was her relationship with Kyle Christie. Although we've loved to see his unserious sense of humor over the years, Kyle's name has indisputably become synonymous with the term "polidicking." The two met and sparked up a romance during Season 31, "Vendettas." Cara Maria even frustratingly chose Kyle for the last spot in the final on his rookie season, instead of choosing "Challenge" veteran and friend Leroy Garrett.

Their sporadic situationship spanned multiple seasons and culminated in name-calling, love triangles, and lots of jealousy — eventually leading to the relationship between Cara Maria and Paulie Calafiore (more on that next). Despite sleeping with multiple other girls in front of Cara Maria during filming of "Final Reckoning," Kyle's intense jealousy caused him and Paulie to target each other for seasons to come. Cara Maria and Kyle remain on bad terms, with Cara Maria having called him a long list of insults. The "Challenge" champ joked with Betches that Kyle's name would come up "if you look up the word f***boy in the dictionary."

Are you sensing a bit of a theme here? Cara Maria and Paulie Calafiore met during filming of Season 32, "Final Reckoning," and sparked up a relationship despite Paulie having a girlfriend at home. Their relationship began when she wanted to use Paulie to make Kyle jealous as he continued shoving his conquests in her face. The couple continued making headlines following the season, due to the complicated love triangle between Paulie, Cara Maria, and his ex, Danielle Maltby ("The Bachelor"). However, they confirmed their open relationship and that they are very much in love on Us Weekly's podcast, "Watch With Us."

Unfortunately, the pair would later end up on viewers' and contestants' bad sides during the airing of "War of the Worlds 2," with fellow challenger Nany González admitting, "The Cara Maria that I saw last season is not the Cara Maria that I want to have in my life" (via People). Cara Maria would prioritize Paulie over her fellow veterans that she'd been working alongside for so many years. Paulie's unapologetic (and unearned) cockiness made him an easy target for the vets. The pair's tunnel vision and overconfidence led them to weasel their way into a final that Paulie wasn't fully equipped for, resulting in a devastating and humiliating loss. Neither Cara Maria nor Paulie have returned for a season since, citing their need for personal time. But, according to their social media, their relationship appears to be stronger than ever.

Nicole Zanatta has proven herself as a bit of a player in the world of MTV reality shows, dating her fair share of women across a variety of different shows. Laurel Stucky, on the other hand, had a few "Challenge" showmances with male challengers, but was never romantically linked to any women ... until Nicole. During Season 29, "Invasion of the Champions," the two women met, and Laurel began forming real feelings for Nicole. Unfortunately, at the time Nicole was pursuing both Laurel and Cara Maria. This spurred one of the most ruthless quotes from Nicole during Episode 9: "Laurel you look good, Cara you look better." Hard to believe the relationship didn't last ...

Cara Maria ended up using this to her advantage in the game as long as she could, much to the disdain of Laurel. The couple continued to go back and forth throughout the season, as Laurel grappled with coming out about her attraction to women, out of fears that it would change the way she was perceived. She eventually came to terms with this and the women continued their relationship without cameras. The relationship didn't last, however, with Laurel sharing that allegations of Nicole's infidelity played into their eventual split. Laurel later showed up during Nicole's season of "Ex On The Beach," where they seemed to have reconciled, even if just for a short time.

There are only a handful of reality television relationships that are able to survive the test of time, and one of them (shockingly) is Jenna Compono and Zach Nichols. They were each recruited to participate in "Battle of the Exes II," where they were sharing a house with each of their exes. Their attraction to one another was instant and they began their roller coaster of a relationship. Jenna and Zach continued their on-again off-again entanglement for five years, with their relationship problems being aired out for the world to see. "He completely dogged her on national television, blocked her phone number, and then completely dropped her, and all she did was love him," explained Laurel, during Episode 6 of "Invasion of the Champions."

Despite the toxicity, it was always clear that neither of them were ready to completely let the relationship go. Zach even joked that he "can't get rid of her" no matter what he does. Even through countless breakups, cheating scandals, and ghostings, Jenna and Zach were almost always involved in each other's lives. After many years of back and forth, the couple finally got back together for good and announced their engagement following "War of the Worlds." Surprisingly, the couple has been going strong ever since. Jenna and Zach got married in a small ceremony in 2021 and are currently expecting their second child.

One of the few healthy relationships that has come out of "The Challenge" is that of Leroy Garrett and Kam Williams — but in reality TV land, there is never a shortage of drama. While Leroy has been involved with "The Challenge" since 2011, Kam didn't join the series until Season 31, but managed to make a name for herself as "Killa Kam" in no time at all. Fans don't know the exact time they began their relationship, but from their first meeting it was clear they would get along well.

Spanning several seasons, Kam and Leroy went back and forth between being romantically involved and just maintaining a friendship. During filming of the "War of the Worlds" reunion, Leroy admitted that his "biggest regret" was sleeping with Kam, because it ruined their friendship (per CheatSheet). However, the two seemed to have worked through a lot of their issues outside of "The Challenge" house, returned for Season 34, and became a much stronger couple from it. When they returned for Season 36, "Double Agents," their joint social game paved the way for Leroy to have arguably his best season of his entire time on the franchise, landing third place. The couple moved in together after, and have since welcomed their first child together.

Brad Fiorenza is good at many aspects of "The Challenge," one of which is finding love. Not only did he meet his now ex-wife and mother of his children during "The Gauntlet III," but he was also notably linked to Britni Thornton since "Vendettas." Rather quickly, they became inseparable. Due to the 10-year age difference and the recency of his divorce, Brad's fellow competitors likened the relationship to a mid-life crisis, but the couple seemed unbothered by outside opinions. 

Their relationship seemed to be going strong when they returned together to compete in Season 32, where challengers were paired with their biggest rivals. Britni was paired with her toxic ex-boyfriend, Chuck, and they each landed in the redemption house not long after the season started. After many drunken outbursts and prolonged sexual tension, Paulie Calafiore spread the lie that Britni and her ex slept together in the redemption house, sending Brad into a tailspin. Britni later announced their breakup in an episode of the "Challenge Mania" podcast, pointing to timing and "loose-ends" he had to tie up with his ex-wife as reasons for their split. 

Brad confirmed to Us Weekly that the events between Britni and Chuck were not the sole reason for their split, but that they definitely made him "uncomfortable." In true "Challenge" fashion, Britni put Brad on blast during the "Final Reckoning" reunion by revealing that he broke up with her as he was dropping her off at the airport after an intimate weekend together (via Hollywood Life).

You remember Jemmye — the girl with a literal fear of ketchup? Back in 2010, Jemmye Carroll and Ryan Knight sparked up a relationship on "The Real World: New Orleans." They later capitalized on their "Real World" fame by entering into "The Challenge," where viewers were shown the on-again off-again nature of their relationship. During his time on MTV, Ryan was always very transparent about his addiction to painkillers and eventual recovery following a hockey injury.

Sadly, on Thanksgiving of 2014, he was found dead after a night of partying. It was reported that the autopsy showed that he died of "accidental acute mixed drug and alcohol intoxication" (via TMZ). Ryan's final season of the series was "Battle of the Exes II," where he was paired with Jemmye. However, the former hockey player passed away before the season aired. Jemmye paid her respects to Ryan in a heartbreaking tweet filled with photos of them looking happy and loved up. She continues to celebrate him any chance she gets and aims to continue sharing his story. Jemmye has spoken out several times about the difficulty of coming to terms with the death of someone so close to her, calling her grief "so overwhelming," and sharing a reminder that "it's ok to not always be ok," in a since-expired Instagram story (via Heavy). 

If you or someone you know is dealing with substance abuse, you can call the Substance Abuse and Mental Health Services Administration (SAMHSA) at 1-800-662-4357. You can also find more information, resources, and support at their website.

Johnny Bananas has had a long list of showmances during his decade-long run on "The Challenge." In the wise words of the "Challenge" champ himself, "There are few things in life that are constants: death, taxes, and Johnny Bananas ..." hooking up with a rookie, that is. When the Banana man showed up for Season 31, he was single for the first time in years, calling himself "single and naked as the day I was born." The flirting began almost instantly between Johnny and Natalie Negrotti, who struck up a fling for most of the season. To most onlookers, the showmance seemed to be mainly for political gain, as Banatalie made their way into the top three several times during the season.

Ultimately, drama plagued the situationship, as one of the challengers in the house dropped the bomb that Bananas actually had a secret hookup with fellow challenger, Kayleigh, in the early days of the season. This resulted in most of the women in the house making Kayleigh their prime target and causing her to leave the competition due to bullying. Johnny and Natalie's relationship turned sour for the remainder of the season, and during "Final Reckoning" and "War of the Worlds." Between seasons, they went through bouts of blocking and unblocking one another. As of publication, the two still don't seem to be have any type of friendship. Natalie told Hollywood Life that their relationship is a "very messed up dysfunctional thing."

Unlike most of the other showmances, Rogan O'Connor and Dee Nguyen's was fairly short-lived, but no less explosive. Their relationship began during "War of the Worlds 2," but was never meant to be serious, despite Dee forming real feelings for him. Near the end of the season, Rogan began conspiring to get Dee thrown into elimination, as he didn't want to have to "drag" her to the final alongside him. Yes, the guy who never saw a single elimination himself and didn't even last one episode during "Vendettas" was worried about dragging someone else to the final ... hard to believe it all went wrong.

This led to the pair going their separate ways, until they each returned for the filming of "Total Madness." While Rogan was attempting to move on with another woman in the house, Dee still had her sights set on him. However, during the airing of "Total Madness" and the height of the Black Lives Matter movement, Dee got caught up in some racism controversy that led MTV and "The Challenge" to completely sever ties with her, editing her out of the remainder of the season. Rogan was also caught in the crossfire around the same time, and ultimately issued an apology for some racist tweets that had resurfaced (via Us Weekly). The two might have only been on "The Challenge" for a short time, but they sure left their mark.