The Challenge’s Cara Maria Sorbello and Paulie Calafiore’s Ups and Downs: A Timeline

Credit: Cara Maria

The Challenge's Cara Maria Sorbello and Paulie Calafiore's Ups and Downs: A Timeline

Sometimes drama leads to a happy ending. That is the case for The Challenge's Cara Maria Sorbello and Paulie Calafiore, who have had their fair share of ups and downs since meeting in 2018. The duo, who first connected on The Challenge: Final Reckoning, had a rough start as they met when he was in a relationship with Bachelorette alum Danielle Maltby. Although they didn't hook up during the show, Sorbello and Calafiore created a bond afterward — before he called things off with Maltby — leading to a very public and messy split. While the Challenge costars continued their romance, the drama didn't end there, as Maltby and Sorbello later realized that he was still talking to them both. “I made a mistake. I f—ked up. I did that, I can own that," he admitted during a December 2018 episode of the "Watch With Us" podcast. At the time, Sorbello added through tears, "I don’t want any of it to be true because I know how I feel about him and I know how we were together. I want all of that to be real so bad." Still — they found their way through it. After driving across the country to try and win the Champs vs Pros winner back, Sorbello and Calafiore started fresh and began dating again months later. [sendtonews type="float" key="7cCXbaiEGD-2836316-14453"] They chose to take a break from Challenges after War of the Worlds 2, telling Us in December 2019 that it was better for their mental health and their relationship. “You can’t put a price tag on happiness. For so long, I was, like, you know the money is so good. I can’t say no. I needed a little break for my own sanity and my own happiness, just finding what makes me me again and get my light back,” she shared with Us. “I’m freakin’ fantastic, so I’m gonna have a little break so they can make someone else the bad guy this next season because I’m not going to be on it!" In October 2021, they opened up exclusively to Us about their status, and why having an "unconventional" relationship really works for them. "I know without a fraction of a doubt in my mind that this man loves me,” she shared at the said. "We are honest with each other. We’re open about what our interests are. A lot of people will hide sexual fetishes or things they like to do because they’re afraid of scaring their partner off. ... This is my person." Scroll down for a full timeline of all their ups and downs through the years: [podcast_block]

Credit: Cara Maria

The Challenge's Cara Maria Sorbello and Paulie Calafiore's Ups and Downs: A Timeline

Sometimes drama leads to a happy ending. That is the case for The Challenge's Cara Maria Sorbello and Paulie Calafiore, who have had their fair share of ups and downs since meeting in 2018. The duo, who first connected on The Challenge: Final Reckoning, had a rough start as they met when he was in a relationship with Bachelorette alum Danielle Maltby. Although they didn't hook up during the show, Sorbello and Calafiore created a bond afterward — before he called things off with Maltby — leading to a very public and messy split. While the Challenge costars continued their romance, the drama didn't end there, as Maltby and Sorbello later realized that he was still talking to them both. “I made a mistake. I f—ked up. I did that, I can own that," he admitted during a December 2018 episode of the "Watch With Us" podcast. At the time, Sorbello added through tears, "I don’t want any of it to be true because I know how I feel about him and I know how we were together. I want all of that to be real so bad." Still — they found their way through it. After driving across the country to try and win the Champs vs Pros winner back, Sorbello and Calafiore started fresh and began dating again months later. [sendtonews type="float" key="7cCXbaiEGD-2836316-14453"] They chose to take a break from Challenges after War of the Worlds 2, telling Us in December 2019 that it was better for their mental health and their relationship. “You can’t put a price tag on happiness. For so long, I was, like, you know the money is so good. I can’t say no. I needed a little break for my own sanity and my own happiness, just finding what makes me me again and get my light back,” she shared with Us. “I’m freakin’ fantastic, so I’m gonna have a little break so they can make someone else the bad guy this next season because I’m not going to be on it!" In October 2021, they opened up exclusively to Us about their status, and why having an "unconventional" relationship really works for them. "I know without a fraction of a doubt in my mind that this man loves me,” she shared at the said. "We are honest with each other. We’re open about what our interests are. A lot of people will hide sexual fetishes or things they like to do because they’re afraid of scaring their partner off. ... This is my person." Scroll down for a full timeline of all their ups and downs through the years: [podcast_block]

Credit: MTV

March 2018

The duo met in March 2018 when they began filming The Challenge: Final Reckoning. At the time, he was dating Maltby, but Sorbello made it known she was very interested in pursuing him.

Credit: Courtesy of MTV(2); Courtesy of CBS

June 2018

After the show wrapped, photos surfaced of Sorbello and Calafiore at an event. In June 2018, Maltby released a statement through her publicist staying that she was "devastated" by the rumors. Four days later, he went on a Twitter rant, stating that he has "tried" to be monogamous but it "doesn't work," writing, "I love women, I have a lot of female friends and sometimes I fall for multiple at a time for different reasons whether it’s the sex or the energy shared between the two of us. I try to be faithful but I can’t."

Credit: Courtesy of Cara Maria Sorbello/Instagram

July 2018

The following month, Final Reckoning premiered and Sorbello told Us exclusively that she is "dating" Calafiore and that she's not seeing other people but has the choice to. "When he’s with me, he’s hands on — holding my hand, telling me I’m beautiful even when I’m disgusting first thing in the morning. You can feel the adrenaline pouring out of his skin when we touch. It is electric," the two-time champ said at the time. "I’ve never been with anybody in the bedroom like him, and I haven’t had anybody treat me like he does, which is amazing. I’m enjoying it, but I still am holding on to that ‘I need to be single’ and I want to be single, but he’s really, really great."

Credit: Courtesy of Cara Maria

July 2018

At the time, the Fresh Meat alum also shared what happened with Maltby. "He told me after the fact, 'I wanted so bad to be able to wait. I wanted to break up with her so that I could be with you.' So, he told me his one regret is not being able to make the call first," Sorbello exclusively told Us. "We did hold off until right before we got our phones back. As soon as he did get his phone back, he did break up with her. It doesn’t make either one of our parts right, but I don’t understand why I’m getting more backlash than the man who did it when it was his relationship."

The pair remained together and left to film The Challenge: War of the Worlds from October to December 2018.

Credit: Courtesy of Danielle Maltby/Instagram

December 2018

The Final Reckoning finale aired on December 4. Later that month, Us confirmed the pair split after she found out he was talking to Maltby again. Though they were in an open relationship, she was under the impression that his relationship with his ex was over — as was Maltby. Both women released text messages to show that he had been talking to both women at the same time.

Credit: MTV (2)

December 2018

The women joined the "Watch With Us" podcast to tell their story together on December 28, both breaking down in tears. Maltby explained that Calafiore FaceTimed and called her after returning from Final Reckoning, telling her he loved her and that he bought her an engagement ring. Sorbello, for her part, said he was sleeping with her in Africa during those messages.

Calafiore joined the podcast following the women's interview, revealing that he had visited Maltby in July in Mexico, where they went to couples counseling, again over Labor Day weekend and another time in October. "I had the opportunity to come clean to Cara and I didn’t until after the articles were out there,” he said. "I was afraid to admit what was going on to Cara because I loved her and she was so free spirited, I thought that she would just leave me. Does that make it right? No. ... 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. I made a mistake. I f—ked up. I did that, I can own that."

Credit: Courtesy of Cara Maria Sorbello

January 2019

The following month, Us confirmed that Calafiore had flown to Montana to visit Sorbello. At the time, a source told Us that she had not "taken him back," but he's working to gain back her trust. "Cara is torn, as every woman would be; she’s still very angry and heartbroken," the insider said. "It’s very tough for her because she wants to be a good example for others, but at the same time, he treated her so well when they were together. She’s torn."

Credit: Courtesy of Cara Maria Sorbello/Instagram

February 2019

The Massachusetts native confirmed the pair were back on the next month, posting multiple Instagram Stories about forgiveness before sharing a pic of them holding hands. 

“And right now… there’s a man out there who patiently adds a new foothold to help him continue to climb no matter how high I build my wall. The harder I push him away, the stronger he holds on to prove why I should let him stay," she wrote at the time. "I regret nothing. How I felt at the time was how I felt. But now, I choose my own happiness. Whatever that means going forward."

Credit: Courtesy of Cara Maria

Summer 2019

From May to July, the duo were both gone filming War of the Worlds 2.

Credit: Courtesy of Cara Maria

August 2019

In August, after filming wrapped, they returned to Montana together and told Us they had "never been happier" at the time. Calafiore noted that after he went to Montana to own up to everything, they hadn't been apart since "A lot has changed. I am now a Montana man,” he shared on the "Watch With Us" podcast, as Sorbello added, "We both made our mistakes but I don’t think I was ever really open and accepting in my own part in it. I just want to get that out there because, everything is falling on you for being the bad guy."

Credit: Courtesy of Cara Maria

October 2021

The couple chose to take time off from The Challenge after the drama and live a quieter life in Montana. In October 2021, they launched their first event for The Ten Escape, a VIP all-inclusive experience, and are in a happy, open relationship. 

"We’re open and people are confused about that. They’re like, ‘Well, they’ve got to be f–king everybody and cheating,'” she told Us at the time. "We’ve come to such a good place. Me, mentally to where I am now and us together. We’ve been with each other through the worst of the worst. We still get excited to see each other. … The sex is good. The love is good. The friendship is good. This is my person.”