The Challenge’s Most Memorable (and Messiest!) Relationships

Credit: Barry King/WireImage; Courtesy of Cara Maria/Instagram

The Challenge’s Most Memorable (and Messiest!) Relationships

While The Real World/Road Rules Challenge began as just that – a competition between two rivaling TV shows, it developed into so much more over the years, and one of the most memorable components is the romances. For some – true love have formed, while others … things have gotten pretty messy. For Cara Maria Sorbello, both apply. “All I want is to fight for the girl who I consider the love of my life. I just want to fight to get Cara back,” Paulie Calafiore told Us Weekly exclusively after War of the Worlds wrapped filming and he was caught up in a love triangle with Cara and his ex Danielle Maltby. He owned up to his mistakes almost immediately and the two – who met on Final Reckoning and exchanged “I love you’s” for the first time on How Far Is Tattoo Far? – are now back together. In fact, they’re moving in together in Montana. “No one will fully know the lengths this man has gone (and the things he continues to do) on his own to prove his intentions and his feelings,” she revealed in February 2019 on Instagram. “So, with one foot out the door, and one foot in, I am moving forward with an open ear and an open heart.” However, they’re not the first couple to have a shaky romance on the MTV reality show. Whether they met on The Real World or Road Rules – we see you, Wes Bergmann – or fell in love and tied the knot after a Challenge season together – a la Tori Hall and Brad Fiorenza – Us Weekly is running down some of the most memorable relationships in Challenge history. Scroll through the gallery for more. [podcast_block]

Credit: Courtesy of Morgan Willett/Instagram

Johnny ‘Bananas’ Devenanzio and Morgan Willett

Willett confirmed to Us Weekly in September 2021 that she and Johnny “Bananas” split. The couple first met in 2018 on The Challenge: War of the Worlds and later confirmed their relationship to Us the following year.

“I’ve always tried my best to be an open book and after seeing everything circulate over the internet, I felt like I should let you all know that Johnny and I are no longer together,” Willett said in a statement on September 27. “While I feel heartbroken, I’m thankful to know the truth. Johnny is someone I loved & respected very much and so I will be taking some time to heal and process it all. Thank you to everyone for the support and when I’m ready to share more, I will. For now, I’m just focused on spending time with my family.”

Credit: Courtesy of Jenna Compono/Instagram

Jenna Compono and Zach Nichols

Although Zach has had his fair share of complicated relationships on The Challenge (Ashley Kelsey, Jonna Mannion, etc.) it appeared like he changed his ways after he met Jenna on Exes II. He then cheated on her when she was away shooting Battle of the Bloodlines. BUT, he’s since apologized and the two have appeared on multiple seasons since; in 2019, Jenna revealed to Us she was moving to Michigan to live with him. In December 2019, the twosome got engaged after Zach proposed to Jenna in front of the Christmas tree in Rockefeller Center in New York City. 

The pair announced they were expecting their first baby in February 2021, one month before they tied the knot. Jenna gave birth to son Anthony in September 2021 and, less than a year later, they found out she was pregnant again. Daughter Liliana arrived in December 2022. They are expecting their third baby in February 2024.

Credit: Courtesy of Britni Thornton/Instagram; Courtesy of Tori Hall/Instagram

Britni Thornton / Brad Fiorenza / Tori Hall

After meeting on The Gauntlet III in 2008, Tori and Brad fell in love, got married and had two kids. However, they called it quits in 2017 and he moved on during season 31 of The Challenge with Britni. While they remain friends, Britni and Brad’s relationship didn’t last.

Credit: Courtesy of Tori Deal/Instagram

Jordan Wiseley and Tori Deal

Tori entered Dirty 30 in a relationship with Derrick Henry, but after he was eliminated, she grew closer to Jordan. During the 2017 Dirty 30 finale, Derrick claimed Jordan and Tori hooked up before she had ended her relationship with him. Regardless, Tori and the Real World: Portland alum are living together in Los Angeles. Us Weekly broke the news in August 2019 that the pair got engaged while filming War of the Worlds 2.

In November 2020, the duo announced that they had called it quits and ended their engagement.

Credit: Mike Coppola/Getty Images

CT Tamburello and Diem Brown

Challenge royalty CT and Diem met on The Duel in 2006 and had an on-off relationship for years. They appeared together on The Duel II and on Battle of the Exes II. He stayed by her side during multiple battles with cancer; she succumbed to the disease in November 2014. 

Credit: MTV

Cara Maria Sorbello and Abram Boise

Cara and Abe clicked immediately in 2010 when meeting on Cutthroat. However, they had their ups and downs through the years and split for good in 2015 when Cara kissed Thomas Buell during Battle of the Bloodlines.

Credit: Courtesy of Cara Maria/Instagram

Cara Maria Sorbello and Paulie Calafiore

During Final Reckoning, Cara Maria and Paulie grew extremely close and admitted to hooking up at the end of the season, despite his relationship with Danielle. He and Danielle parted ways and he was in an open relationship with Cara throughout filming of The Challenge: War of the Worlds. When they returned from filming, Cara found out he was still seeing Danielle and called off their relationship. In January 2019, the two got back together and he moved to Montana shortly after to be with her.

Credit: MTV

Jemmye Carroll and Ryan Knight

During The Real World: New Orleans, Jemmye and Knight entered a messy yet sweet relationship. The two had an on-off relationship over the years, appearing on Battle of the Seasons, Rivals II, and Battle of the Exes II. Shortly after the last wrapped filming, he died of an overdose in November 2014.

Credit: Getty Images(3)

Wes Bermann / Johanna Botta / Kenny Santucci

Wes and Johanna first met on The Real World: Austin and began a relationship shortly after it wrapped. They then both joined Fresh Meat, as a couple. They got engaged and bought a house together but broke up two years later. In 2008, she hooked up with Kenny Santucci on The Island. The following year, Kenny, Johanna, Wes and his then-girlfriend KellyAnne Judd, all competed on The Ruins.

Credit: Evan Agostini/Getty Images

Danny Jamieson and Melinda Stolp

Another Real World: Austin duo! Danny and Melinda fell in love when they joined the 2005 season of The Real World; she moved to Boston after the show wrapped and they were engaged by the reunion show. They tied the knot in 2008, but on Cutthroat in 2010, Melinda revealed they were divorcing. She remarried in 2016.

Credit: MTV

Robin Hibbard and Mark Long

In 2004, Challenge beasts Robin and Mark began dating on Battle of the Sexes II. They reportedly lived together for some time – though he denies that – but eventually called it quits. However, they proved they could still compete when they entered Battle of the Exes as a team in 2012.