Unforgettable and Chaotic Love Connections on The Challenge: A Rollercoaster of Passion and Drama!

The Real World/Road Rules Challenge initially started as a rivalry between two TV shows but has evolved into something much greater over time, with the romances standing out as one of the most memorable aspects. Cara Maria Sorbello's experience with love falls into both categories - true love has blossomed for some, while things have become quite complicated for others.

Paulie Calafiore, speaking exclusively to us after the conclusion of War of the Worlds, expressed his desire to fight for the love of his life, Cara. Following a complicated love triangle involving his ex, Danielle Maltby, Paulie took responsibility for his actions and has now reconciled with Cara. Their relationship has progressed to the point where they are planning to move in together in Montana. In February 2019, Cara acknowledged Paulie's relentless efforts to prove his true intentions and feelings, stating that she is cautiously moving forward with an open mind and heart.

However, they are not the first couple to have a tumultuous romance on the MTV reality show. Whether they crossed paths on The Real World or Road Rules – we acknowledge you, Wes Bergmann – or formed a deep connection and got married after a season together on The Challenge – like Tori Hall and Brad Fiorenza – We is presenting a roundup of the most unforgettable relationships in Challenge history. Take a look at the gallery for more.

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

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

Some have found true love, while others have faced complications. Cara Maria Sorbello falls into both categories.

Paulie Calafiore expressed his desire to fight for the woman he considers the love of his life. After being caught in a love triangle with Cara and his ex Danielle Maltby during the filming of War of the Worlds, Paulie admitted his mistakes and reconciled with Cara. The couple, who initially met on Final Reckoning and exchanged "I love you's" on How Far Is Tattoo Far?, are now back together and planning to move in together in Montana.

"He has gone to great lengths, continuously, to prove his intentions and feelings," she shared on Instagram in February 2019. "With one foot out the door and one foot in, I am moving forward while remaining receptive and open-hearted."

However, they are not the first couple to experience a tumultuous romance on the MTV reality show. Whether they met on The Real World or Road Rules – we can't forget about Wes Bergmann – or fell in love and got married after a season on The Challenge – like Tori Hall and Brad Fiorenza – We are recapping some of the most memorable relationships in Challenge history.

Scroll through the gallery for more.

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Credit: Courtesy of Morgan Willett/Instagram

Johnny ‘Bananas’ Devenanzio and Morgan Willett

In September 2021, it was confirmed by Willett that her relationship with Johnny "Bananas" ended. They initially met in 2018 while filming The Challenge: War of the Worlds, and their romantic involvement was later confirmed to Us the following year.

“I’ve always strived to be transparent, but with the countless rumors circulating on the internet, I felt the need to inform you all that Johnny and I have decided to part ways,” stated Willett on September 27. “Though my heart aches with this newfound reality, I appreciate knowing the truth. Johnny was someone I deeply cared for and admired, thus I will take the necessary time to heal and process my emotions. I truly appreciate the support from everyone, and when I am ready to divulge more, I promise to do so. Currently, my priority lies in spending quality time with my loved ones."

Credit: Courtesy of Jenna Compono/Instagram

Jenna Compono and Zach Nichols

Zach has had complicated relationships in the past on The Challenge with Ashley Kelsey, Jonna Mannion, and others. However, it seemed like he changed his behavior after meeting Jenna on Exes II. Unfortunately, he cheated on her while she was filming Battle of the Bloodlines. Despite this, he has apologized and the two have continued to participate in multiple seasons together. In 2019, Jenna shared with Us that she was moving to Michigan to live with Zach. The couple got engaged in December 2019 when Zach proposed to Jenna in front of the Christmas tree in Rockefeller Center in New York City.

They made the exciting announcement in February 2021 that they were expecting their first child, and just a month later, they got married. Jenna gave birth to their son Anthony in September 2021. Less than a year later, they discovered she was pregnant again, and their daughter Liliana was born in December 2022. Their third baby is expected to arrive in February 2024.

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

Britni Thornton / Brad Fiorenza / Tori Hall

Tori and Brad's love story began on The Gauntlet III in 2008, leading to their marriage and the blessing of two children. However, their union came to an end in 2017, when Brad found new love during season 31 of The Challenge with Britni. Although they maintain a friendship, Britni and Brad's romantic relationship ultimately wasn't meant to last.

Credit: Courtesy of Tori Deal/Instagram

Jordan Wiseley and Tori Deal

Tori initially joined Dirty 30 with her boyfriend Derrick Henry by her side, but their relationship took a turn when he got eliminated. It was during this time that she grew closer to Jordan. In the finale of Dirty 30 in 2017, Derrick made a claim that Tori and Jordan had been involved while she was still with him. However, despite the controversy, Tori and the former cast member of Real World: Portland are currently residing together in Los Angeles. In August 2019, we were the first to report that they became 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

Royalty CT and Diem crossed paths on The Duel in 2006 and embarked on a tumultuous romance that endured many ups and downs throughout the years. Together, they made appearances on The Duel II and Battle of the Exes II. CT stood firmly by Diem's side as she faced several harrowing battles against cancer. Unfortunately, she tragically succumbed to the disease in November 2014.

Credit: MTV

Cara Maria Sorbello and Abram Boise

Cara and Abe instantly connected in 2010 after meeting on Cutthroat. However, their relationship had its highs and lows over the years and came to an end in 2015 when Cara unexpectedly 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 formed a strong bond and confessed to engaging in a romantic relationship at the conclusion of the season, despite Paulie being involved with Danielle at the time. Subsequently, Paulie and Danielle ended their relationship, and he embarked on an open partnership with Cara during the filming of The Challenge: War of the Worlds. Following their return from filming, Cara discovered that Paulie was still involved with Danielle, prompting her to terminate their relationship. In January 2019, the couple reconciled, leading Paulie to relocate to Montana shortly afterward in order to be with Cara.

Credit: MTV

Jemmye Carroll and Ryan Knight

During The Real World: New Orleans, Jemmye and Knight embarked on a tumultuous yet endearing romance. Their relationship had its ups and downs as they appeared together on various reality shows such as Battle of the Seasons, Rivals II, and Battle of the Exes II. Tragically, he passed away in November 2014 due to an overdose, shortly after the completion of filming.

Credit: Getty Images(3)

Wes Bermann / Johanna Botta / Kenny Santucci

Wes and Johanna crossed paths for the first time on The Real World: Austin and soon after, they embarked on a romantic journey. Their love story continued as they participated in Fresh Meat, entering as a couple. They eventually made the commitment to get engaged and even bought a house together. However, their relationship came to an end two years later. In 2008, Johanna found a connection with Kenny Santucci during their time on The Island. The following year, both Kenny and Johanna, along with Wes and his then-girlfriend KellyAnne Judd, all took part in the competitive reality show, The Ruins.

Credit: Evan Agostini/Getty Images

Danny Jamieson and Melinda Stolp

Another Real World: Austin duo! Danny and Melinda fell in love during their participation in the 2005 season of The Real World. Following the conclusion of the show, Melinda relocated to Boston and they officially got engaged during the reunion show. They exchanged vows in 2008; however, their marriage took a turn when Melinda disclosed their decision to divorce while on Cutthroat in 2010. Interestingly, in 2016, Melinda found love once again and remarried.

Credit: MTV

Robin Hibbard and Mark Long

Challenge competitors Robin and Mark, known for their formidable skills, first sparked a romantic connection during the Battle of the Sexes II in 2004. Although there were rumors of them residing together, Mark denies this claim. Eventually, their relationship came to an end. Nonetheless, they showcased their unwavering competitive spirit when they formed a formidable team in the 2012 edition of Battle of the Exes.