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."

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.

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."

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.

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.

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.

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.