Colton Underwood and Cassie Randolph’s Messy Split: Everything We Know

Credit: Broadimage/Shutterstock

Colton Underwood and Cassie Randolph’s Messy Split: Everything We Know

It didn’t take long for Colton Underwood and Cassie Randolph’s split to turn into a battle of he said, she said. Underwood and Randolph met while filming season 23 of The Bachelor, which aired in 2019. While the graduate student quit the show during the final weeks, telling Underwood that she wasn’t ready to get engaged, he attempted to stop her from leaving by breaking up with the remaining women, Hannah Godwin and Tayshia Adams. The twosome subsequently reunited and ended the show as a couple. After the show wrapped, Randolph told  Us Weekly that they didn’t “have a timeline” to get engaged. “We’ve definitely talked about it, but we’re just enjoying right now and not worrying about it,” she said at the time. In Underwood’s 2020 book, The First Time, he revealed that the pair briefly called it quits in August 2019. After their brief hiatus, they celebrated their first anniversary that November. “I thought it was important to share and shed light that you know, real things,” Underwood told Us in April 2020 about including the split in the memoir. “Our circle was violated, about information, getting out that we didn’t know how it got out and how it became public. But I think that’s in itself [became] a battle within our relationship. … And I thought it was important to share just because it shows that we are we still real people with real emotions in this relationship, and we’re trying to figure out what to do with everybody else sort of, in always in our business.” [jwplayer pxjkjYSN-l3ahXupL] A month later, Underwood and Randolph announced they were going their separate ways. "Colton and I have broken up, but have decided to remain a part of each others lives,” she wrote via Instagram at the time. “With all that we have gone through, we have a special bond that will always be there," she 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." Why did Colton Underwood have to stay 100 yards away from Cassie Randolph? Hear the alleged crazy texts he sent her that earned him a restraining order. In under 2 minutes! Underwood, who battled the coronavirus in March 2020, noted it’s “been a crazy few months” for the twosome. “Cass and I have been doing a lot of self-reflecting,” he wrote on Instagram at the time. “Sometimes people are just meant to be friends – and that’s OK. 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.” Scroll through for all of the details of the drama that followed their split:

Credit: Broadimage/Shutterstock

Colton Underwood and Cassie Randolph’s Messy Split: Everything We Know

It didn’t take long for Colton Underwood and Cassie Randolph’s split to turn into a battle of he said, she said. Underwood and Randolph met while filming season 23 of The Bachelor, which aired in 2019. While the graduate student quit the show during the final weeks, telling Underwood that she wasn’t ready to get engaged, he attempted to stop her from leaving by breaking up with the remaining women, Hannah Godwin and Tayshia Adams. The twosome subsequently reunited and ended the show as a couple. After the show wrapped, Randolph told  Us Weekly that they didn’t “have a timeline” to get engaged. “We’ve definitely talked about it, but we’re just enjoying right now and not worrying about it,” she said at the time. In Underwood’s 2020 book, The First Time, he revealed that the pair briefly called it quits in August 2019. After their brief hiatus, they celebrated their first anniversary that November. “I thought it was important to share and shed light that you know, real things,” Underwood told Us in April 2020 about including the split in the memoir. “Our circle was violated, about information, getting out that we didn’t know how it got out and how it became public. But I think that’s in itself [became] a battle within our relationship. … And I thought it was important to share just because it shows that we are we still real people with real emotions in this relationship, and we’re trying to figure out what to do with everybody else sort of, in always in our business.” [jwplayer pxjkjYSN-l3ahXupL] A month later, Underwood and Randolph announced they were going their separate ways. "Colton and I have broken up, but have decided to remain a part of each others lives,” she wrote via Instagram at the time. “With all that we have gone through, we have a special bond that will always be there," she 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." Why did Colton Underwood have to stay 100 yards away from Cassie Randolph? Hear the alleged crazy texts he sent her that earned him a restraining order. In under 2 minutes! Underwood, who battled the coronavirus in March 2020, noted it’s “been a crazy few months” for the twosome. “Cass and I have been doing a lot of self-reflecting,” he wrote on Instagram at the time. “Sometimes people are just meant to be friends – and that’s OK. 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.” Scroll through for all of the details of the drama that followed their split:

Credit: Danny Moloshok/Invision/AP/Shutterstock

The Split

According to Randolph’s court documents, the twosome went their separate ways in mid-April. They announced their breakup on May 29, 2020.

“Breaking up was not an easy decision for Colton and Cassie, but they believe it was the right decision at the end of the day,” a source told Us at the time. “It was not something they did lightly. They had a number of conversations about their future beforehand. Now that all is said and done, they are starting a new chapter as friends.”

Credit: ABC

The ‘Bachelor: GOAT’ Drama

Less than two months after their split news went public, Randolph filmed an interview with Chris Harrison for an episode of The Bachelor — The Greatest Seasons Ever! While she played coy about the reason for their split, Underwood made it clear he wasn’t happy with her decision.

“When our relationship ended we agreed to handle things as privately as possible as we attempted to navigate our new relationship as friends,” he wrote on July 9, 2020, via Instagram. “I chose to do that since we were living in this interim period, but obviously a lot changed this week.”

Randolph took to Instagram to fire back.

“I want to show appreciation. I didn’t see any harm in doing the interview, as I wasn’t going to dish out details about our relationship to them,” she wrote. ”It seems you are subtly engaging in a tactic that peppers in aggressive comments such as ‘that obviously changed this week’ in order to make me look like the bad one. I would also like to ask that you don’t cloud our great, 1 1/2 year relationship with a messy breakup.”

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The Book Debacle

Amid the Bachelor: GOAT drama, Randolph also accused Underwood of trying to make money off their breakup through a new chapter of his book, The First Time.

“You informed me you intend to monetize our breakup by writing a new chapter to discuss your experience with COVID (where you stayed in my family’s house during your recovery and about our breakup),” she wrote. “You have also refused to give me any sort of approval on the chapter you will be writing, which will heavily feature me … This seems a bit unfair to me. Colton, you can do what you want, but please do not have a double standard.”

A rep for Underwood subsequently told Us that Randolph’s claims were “simply not true.” The former football player later claimed during an August 2020 appearance on Reality Steve’s podcast that the two exes came together to work on the new chapter of his book, which is set to be released in January 2021.

“I have nothing but good things and love and well-wishes and friendship with Cassie right now. I love the girl and miss the girl dearly … What bugged me on [The Bachelor: GOAT] was the fact that that show took advantage of her, ” he said on August 13, 2020. “The chapter is part our breakup and part me having COVID. We go into the details that we’re comfortable sharing in that chapter and we both went over it together. … Honestly, I think her being a part of it made it even better.”

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The Unfollowing

In late August 2020, fans noticed Randolph and several members of her family unfollowed Underwood on Instagram. He subsequently stopped keeping up with her on the social media app. By that September, Randolph wiped Underwood from her account.

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Cassie’s Claims

News broke on September 11, 2020, that Randolph was seeking a restraining order against Underwood, citing Domestic Violence Prevention. In the court documents obtained by Us, Randolph accused her ex of “stalking and harassing her,” sending “unsettling text messages” and placing “a tracking device on her vehicle.” She also alleged that he took “obsessive” walks to her Huntington Beach, California, family home and apartment, claiming her family and friends have spotted him outside her properties at all hours of the night.

Us confirmed on September 14, 2020, that Underwood was ordered stay at least 100 yards away from Randolph, her house, her car and workplace. He was also instructed not make “contact, either directly or indirectly, in any way” with his ex.

Credit: Michael LeBrecht/ABC

The Text Messages

Randolph provided a series of text messages between her and Underwood in her court docs. “It’s crazy to think we used to be in a position of love,” Underwood wrote to Randolph in June 2020, calling her “shady” and accusing her of lying about spending time with an ex-boyfriend.

One message read, “I ask myself all the time how someone who I loved and loved me could do the things they do and say the things they do.”

In July, Underwood wrote that he had “a million questions” that he didn’t know if he wanted the answers to. “My heart hurts a lot right now and I miss my best friend, my lover and the one person I never expected to lose,” he texted her.

Randolph also accused Underwood of texting her via “alias phone numbers” and claimed he confessed to doing so. She provided examples. One series of messages read, “You like playing games huh? Let’s play some games then,” one of the anonymous texts Randolph received read. “Let’s just say we used to be family friends … Have your good time. .. you’ll have nothing but regrets later with how you treat people  … Totally seems like you’re growing up. Lolz Living at home still.”

Credit: Josh Vertucci/ABC

Colton’s Initial Response

“As this is a legal matter, we cannot provide any comment at this time,” a rep for Underwood told Us after the details of the restraining order were made public.

Credit: Courtesy of Instagram/Colton Underwood

The Reality Show

A source confirmed to Us that Randolph and Underwood had been in production on a reality series during the summer of 2020. They have both since pulled out of the project.

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The Police Report

The night before their court date, the speech pathologist filed a police report against Underwood over the tracking device in her car. “It was her intention to first try and work through this process privately in a manner that gives both her and Colton safety, security and respect,” her attorney, Bryan Freedman, said. “We are confident this is possible.”

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Dropped

Three days before Underwood and Randolph’s scheduled November 6 court date, he broke his silence, telling Us that she filed to dismiss the order against him.

“Today Cassie asked the court to dismiss the temporary restraining order against me,” Underwood told Us in a statement on November 3, 2020. “The two of us were able to reach a private agreement to address any of Cassie’s concerns. I do not believe Cassie did anything wrong in filing for the restraining orders and also believe she acted in good faith. I appreciate everyone’s respect for privacy regarding this matter.”

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Coming Out

In April 2021, Underwood came out as gay during an interview on Good Morning America. During the interview, he said he was in love with Randolph and apologized for the messy breakup.

"I loved everything about her, and it’s hard for me to articulate exactly what my emotions were in going through that relationship with her was because I obviously had an internal fight going on,” he said at the time. “I would just say that I’m sorry from the bottom of my heart."