Colton Underwood‘s past relationship with Cassie Randolph — and her restraining order against him — resurfaced during his stint on The Traitors, but what actually happened between the exes?
Underwood’s love life became a topic of conversation on The Bachelorette when he joined Becca Kufrin’s season 14 in 2018. He later appeared on season 5 of Bachelor in Paradise before becoming the season 23 Bachelor lead in 2019.
The reality star formed a connection with Randolph that resulted in that iconic fence-jumping scene. Despite ending the show together, the couple didn’t get engaged but remained in a relationship for a year after The Bachelor.
After their split, Us Weekly confirmed in September 2020 that Randolph was granted a restraining order against Underwood. She claimed he was stalking and harassing her. The case was dropped in November 2020, and Underwood came out as gay the following year.
When Did Colton Underwood and Cassie Randolph Meet?
Colton Underwood and Cassie Randolph formed a connection on season 23 of The Bachelor, which premiered in January 2019. Randolph later told Underwood she loved him but wasn’t ready to be engaged, so she chose to leave the show. Underwood, meanwhile, was so upset that he jumped over a fence and tried to leave as well.
During the March 2019 finale, Underwood cut ties with the other women and went to Randolph’s hotel room to reconcile.
How Long Did Colton Underwood and Cassie Randolph Date?
After their time on The Bachelor came to an end, Colton Underwood and Cassie Randolph dated for over a year.
“It was a lot of changes, for sure, because we went from these more simple, more normal lives and then all of a sudden, we film a show and then you’re thrown into craziness where everyone is very hyperaware of everything that goes on in your life and your relationship,” Randolph told Us in October 2019 about adjusting to a romance in the public eye. “It was a little bit of a struggle at first, I think — like adjusting to everything. But I feel like now we’ve kind of gotten used to it and learned to balance everything a lot more.”
Underwood pointed out that the show helped them grow their relationship.
“I think you learn to communicate too,” he explained. “Just with whether it’s tabloids or someone speculating a certain thing or people reading into your body language, you know. You just learn how to communicate with each other and you’ll be on the same page with everything going on. … Nobody could ever prepare you for what life is like after that. Like, you can have people tell you all you want, like, ‘Oh, wait for this, wait for this.’ But until you’re in it, you don’t really get the full magnitude of it.”
When Did Colton Underwood and Cassie Randolph Break Up?
Colton Underwood and Cassie Randolph revealed via Instagram in May 2020 that they had decided to call it quits.
“Colton and I have broken up, but have decided to remain a part of each others lives. With all that we have gone through, we have a special bond that will always be there,” Randolph wrote at the time. “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 Cassie Randolph Request a Restraining Order Against Colton Underwood?
Following some public back-and-forth in the wake of their split, news broke in September 2020 that Cassie Randolph filed a restraining order against Colton Underwood, claiming he had planted a tracking device in her car, harassed her via text message and showed up uninvited to her apartment and her parents’ house after their breakup.
The order was granted, forcing Underwood to stay at least 100 yards away from Randolph. He was also ordered not to contact her.
Two months later, Underwood revealed that the case had been settled privately, and the restraining order was dropped.
How Did Colton Underwood Address the Scandal?
Colton Underwood broke his silence about his personal life when he came out on Good Morning America in April 2021. He claimed that he was previously very much in love with Cassie Randolph, which caused confusion and led to a tumultuous breakup.
“I’m sorry for any pain and emotional stress I caused,” he said. “I wish that it wouldn’t have happened the way that it did. I wish that I had been courageous enough to fix myself before I broke anybody else.”
Later that year, Underwood addressed the legal drama again on his Netflix docuseries, Coming Out Colton.
“I think that [the restraining order] was sort of a huge wake-up call. I’m sad that it even got to that point to where that had to be my wake-up call, and me affecting other people in my life was sort of the moment that I realized I had to come out,” he told Us in December 2021. “Obviously, I wish I would have had the courage to come out without having to be pushed.”
Randolph was asked to be part of the series, but she declined.
Has Cassie Randolph Said Anything About the Legal Drama?
Cassie Randolph, who has been married to Brighton Reinhardt since 2025, has remained largely tight-lipped about what happened with Colton Underwood. She made a rare comment in March 2022 on Kaitlyn Bristowe’s “Off the Vine” podcast, saying, “I haven’t talked about it, so it’s really hard for me to talk about it at all, or even know the right thing to say when addressing it. I feel so much pressure when asked about it that I would love to be able to be open and candid about things, but I’m just not there yet. I’m sure I will one day want to speak on it because there’s just a lot there.”
Randolph also claimed that her ex didn’t give her a heads-up that he was planning to come out on national TV. “I found out the same way that everyone else did,” she recalled. “I was actually in Mexico on vacation with friends. … But yeah, I found out, I think, through Snapchat on GMA. It was horrible. It was just, like, a shocking kind of feeling. ”
Later that year, Randolph issued a message to Underwood.
“I’m very happy that he is … at peace with himself and not carrying that burden anymore, of course,” Randolph said on an October 2022 episode of the “Ben and Ashley I Almost Famous” podcast. “It was a very, just, overall hard time for me, so I feel like there was just one thing after another and I was just extremely overwhelmed with everything going on.”
Why Was Colton Underwood’s Past With Cassie Randolph Revisited?
Colton Underwood appeared on season 4 of The Traitors in early 2026, which led to backlash from viewers who knew about his issues with Cassie Randolph.
“I met with production. I met with Peacock. I was like, ‘I’m down to do this.’ Because this show is about strategy. It is about the game. It is about traitors. It is not personal,” he explained to Vanity Fair in February 2026 about trying to keep the narrative off the show. “My only ask is, like, if I do this, I don’t want people to bring up anything outside of the game. I have a family now, right? I’m … so far past what happened six years ago.”
Underwood addressed what happened with Randolph at the reunion after not discussing it during the season.
“I think what I can understand from people viewing me back on television, if you didn’t follow my story and what I went through, and you watched me as the Bachelor in 2019, and then, all of a sudden, you’re tuning in in 2026,” he said. “I had an incredibly difficult couple of years, and I’ve grown, I’ve changed. I’ve put in so much work into myself and to my family. I never really thought the way that I would show up and play Traitors would be linked to one of the darkest and most horrible moments of my life.”
Have Colton Underwood and Cassie Randolph Spoken Since the Restraining Order Was Dropped?
“I have no contact. If she ever did reach out or want to reach out, I would be open to answering any questions that her or her family would have for me,” Colton Underwood told Vanity Fair in February 2026. “That is something I’ve always offered. I’m in no position to really say much more than that or reach out. There’s been no part of me that would. I would always be up for it. It’s all on her terms.”
Underwood reflected on what led to the messy breakup.
“It was 2020. It was, as people remember, COVID. I was fully convinced that she was gonna be my last straight … like, I was going to have to either kill myself or come out. That’s just transparently, like, where my mindset was,” he elaborated. “I don’t know if this is the right phrase, but it was somewhat of the perfect storm of me hitting rock bottom, of me really trying to navigate, ‘Am I gonna kill myself or am I gonna come out?’ That’s just where I was at.”
Underwood, who is now married to husband Jordan C. Brown, also revealed he was being blackmailed about his sexuality at the time and was “struggling with Xanax and prescription medications.”
“It was a pretty intense moment in my life where I made some really, really poor decisions. The difficult part now is seeing the people who have a lot to say about what happened six years ago,” he noted. “It’s lacking a lot of the context of where our world was at, but also where I was at, the state of mind that I was in.”
Underwood continued: “The pressures and the threats that I was going through. I will always take accountability. I will always own mistakes that I made. But everything that you’re seeing on social media — these videos, these people who have a lot to say — is not correct.”
If you or someone you know is experiencing domestic violence, please call the National Domestic Violence Hotline at 1-800-799-7233 for confidential support. If you or someone you know is struggling or in crisis, help is available. Call or text 988 or chat at 988lifeline.org.
