Colton Underwood Went Through ‘Excruciating Pain’ After Cassie Randolph Split and More Revealed in New ‘The First Time’ Chapter

Credit: Scott Kirkland/Shutterstock; Michael Simon/startraksphoto.com (inset)

Colton Underwood Went Through 'Excruciating Pain' After Cassie Randolph Split and More Revealed in New 'The First Time' Chapter

Telling the full story. On Tuesday, January 26, Colton Underwood released the paperback version of The First Time: Finding Myself and Looking for Love on Reality TV. The memoir, released in March 2020, chronicled his time on The Bachelorette, Bachelor in Paradise and The Bachelor, where he met and fell in love with Cassie Randolph. The paperback version includes a new chapter, titled "The Next Chapter," which the former NFL player, 29, wrote in July 2020. The following month, he revealed that Randolph, 25, signed off the new pages, which detail his battle with coronavirus and their breakup, which they revealed via Instagram in May 2020. "It's been a crazy few months to say the least, Cass and I have been doing a lot of self-reflecting. Sometimes people are just meant to be friends — and that's okay. We both have grown immensely and been through so much together — so this isn't the end of our story, it's the start of a whole new chapter for us," the season 23 Bachelor wrote via Instagram at the time. She echoed the statement, noting that "neither" of them were ready to share their split news but felt that they needed to. [jwplayer pisLAt7X] "Colton and I have broken up, but have decided to remain a part of each other's lives. With all that we have gone through, we have a special bond that will always be there," the California native wrote. "I love Colton very much and have an enormous amount of respect for him. We have both learned and grown so much these past couple years, and will always have each other's back. Always." However, the process of posting that statement was much more emotional that it seemed, he explained in the new chapter. Scroll through the gallery for everything Underwood revealed in "The Next Chapter." Hear the Us Weekly editors break down the most surprising celebrity births during the pandemic in under 2 minutes!

Credit: Scott Kirkland/Shutterstock; Michael Simon/startraksphoto.com (inset)

Colton Underwood Went Through 'Excruciating Pain' After Cassie Randolph Split and More Revealed in New 'The First Time' Chapter

Telling the full story. On Tuesday, January 26, Colton Underwood released the paperback version of The First Time: Finding Myself and Looking for Love on Reality TV. The memoir, released in March 2020, chronicled his time on The Bachelorette, Bachelor in Paradise and The Bachelor, where he met and fell in love with Cassie Randolph. The paperback version includes a new chapter, titled "The Next Chapter," which the former NFL player, 29, wrote in July 2020. The following month, he revealed that Randolph, 25, signed off the new pages, which detail his battle with coronavirus and their breakup, which they revealed via Instagram in May 2020. "It's been a crazy few months to say the least, Cass and I have been doing a lot of self-reflecting. Sometimes people are just meant to be friends — and that's okay. We both have grown immensely and been through so much together — so this isn't the end of our story, it's the start of a whole new chapter for us," the season 23 Bachelor wrote via Instagram at the time. She echoed the statement, noting that "neither" of them were ready to share their split news but felt that they needed to. [jwplayer pisLAt7X] "Colton and I have broken up, but have decided to remain a part of each other's lives. With all that we have gone through, we have a special bond that will always be there," the California native wrote. "I love Colton very much and have an enormous amount of respect for him. We have both learned and grown so much these past couple years, and will always have each other's back. Always." However, the process of posting that statement was much more emotional that it seemed, he explained in the new chapter. Scroll through the gallery for everything Underwood revealed in "The Next Chapter." Hear the Us Weekly editors break down the most surprising celebrity births during the pandemic in under 2 minutes!

Credit: Courtesy Cassie Randolph/Instagram

His COVID-19 Battle Put Stress on Their Relationship

"The situation was unfortunate, impossible to predict, incredibly trying, and surreal. And while I won’t say it led to our breakup, it did subject our relationship to extraordinary stress and strain, as it did to so many people’s lives," Underwood wrote in the new chapter. He added that after a week of remaining in the guest bedroom of Randolph's family home with a fever, he finally was able to come downstairs. "I regret that I was sometimes more stupid than smart when it came to always wearing a mask and going to extreme lengths to ensure I kept my germs far away from Cass’s family," he wrote. "Michelle [Randolph] said she couldn’t be around me—and the virus — anymore and booked it back to Los Angeles to be with her boyfriend. I heard similar tension in Cass’s voice. “'It’s hard to explain what this is doing to everyone,' she said."

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Cassie Initiated the Breakup Months Before They Posted

Shortly after he recovered, he was blindsided by Cassie saying that she was struggling with their relationship. They tried to spend time together and get back to normal but it didn't work. In April, he moved the rest of his stuff out of her house.

"Her birthday was a few days later. I felt sad about missing it even though we were broken up, and I drove down there at the last minute, had dinner, celebrated with her family and friends, and then returned to LA. Two days later, I drove to Colorado. I wanted to be with my family and put some distance between me and Cass so I didn’t feel the temptation to be near her," the athlete wrote, adding that they talked frequently while he was there "making some progress, talking through issues [and] agreeing to disagree," but she still wanted to post the split statement via social media.

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They Cried Over FaceTime While Posting Their Split Statement

Eventually, he gave in. "I suppose I was the kid on the high dive who needed a push. Otherwise he’d never jump. You don’t need to be a therapist to understand why I was so resistant. I didn’t want to break up. I didn’t want to accept that Cass wanted to break up with me. I didn’t want it to be over. I didn’t want any of this to be real," he shared. Still, on May 29, they posted at the same time while on FaceTime with each other and cried.

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They Spent the Night Together Post-Split

After time passed, the reality star called Cassie for dinner and they met up in L.A. "We hit it off like none of the past five months had ever happened. Afterward, she came back to my place, where we had a few drinks, hung out, and we were Colton and Cass again the rest of that night. Then, when we woke up the next morning, I could tell everything was different," he recalled. "I had the urge to say I love you before she walked out the door, and I sensed she did, too. No door shut that softly has ever made a louder sound."

Credit: Stewart Cook/Shutterstock; Sara De Boer/startraksphoto.com

The Breakup Was 'Excruciating'

The split hit Underwood hard, he admitted in the chapter. "Falling in love is like open-heart surgery. Breaking up is like seeing your heart in someone else’s hands and realizing the anesthesia has worn off. Geez, it hurt," he wrote. "The pain was excruciating. But not nearly as bad as it would have been if I’d never had that relationship with Cass."

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He'll Always Love Her

Despite the split, he believes that they were both in love and "now that time has passed, I believe both of us have remained in love with each other and always will be."

He added, "I know Cass famously said on television that she loved me but wasn’t in love with me, and in retrospect that is so Cassie: true, conflicted, confused, not wanting to hurt, trying to avoid being hurt, and in the end following her heart. She followed her heart to me. I have no doubt she was in love with me just as I was in love with her."

In September 2020, Cassie filed a restraining order against Underwood, also claiming in the documents that he had placed a tracking device on her car. The following month, the restraining order was dropped.