Colton Underwood‘s previous relationship with Cassie Randolph — and her restraining order in opposition to him — resurfaced throughout his stint on The Traitors, however what truly occurred between the exes?
Underwood’s love life grew to become a subject of dialog on The Bachelorette when he joined Becca Kufrin’s season 14 in 2018. He later appeared on season 5 of Bachelor in Paradise earlier than turning into the season 23 Bachelor lead in 2019.
The truth star fashioned a reference to Randolph that resulted in that iconic fence-jumping scene. Regardless of ending the present collectively, the couple didn’t get engaged however remained in a relationship for a 12 months after The Bachelor.
After their cut up, Us Weekly confirmed in September 2020 that Randolph was granted a restraining order in opposition to Underwood. She claimed he was stalking and harassing her. The case was dropped in November 2020, and Underwood got here out as homosexual the next 12 months.
Colton Underwood’s relationships made headlines earlier than and after he joined Bachelor Nation. Underwood fell quick for Olympian Aly Raisman after being arrange by a good friend. “Aly was straightforward to speak to. She was open, humorous, brilliant, sincere, and inquisitive. She laughed simply and had a smile that I’d’ve been pleased to easily gaze (…)
When Did Colton Underwood and Cassie Randolph Meet?
Colton Underwood and Cassie Randolph fashioned a connection on season 23 of The Bachelor, which premiered in January 2019. Randolph later informed Underwood she beloved him however wasn’t able to be engaged, so she selected to depart the present. Underwood, in the meantime, was so upset that he jumped over a fence and tried to depart as properly.
Throughout the March 2019 finale, Underwood reduce ties with the opposite girls and went to Randolph’s lodge room to reconcile.
How Lengthy Did Colton Underwood and Cassie Randolph Date?
After their time on The Bachelor got here to an finish, Colton Underwood and Cassie Randolph dated for over a 12 months.
“It was numerous adjustments, for positive, as a result of we went from these extra easy, extra regular lives after which hastily, we movie a present and you then’re thrown into craziness the place everybody could be very hyperaware of all the things that goes on in your life and your relationship,” Randolph informed Us in October 2019 about adjusting to a romance within the public eye. “It was a little bit little bit of a wrestle at first, I feel — like adjusting to all the things. However I really feel like now we’ve form of gotten used to it and realized to stability all the things much more.”
Underwood identified that the present helped them develop their relationship.
“I feel you study to speak too,” he defined. “Simply with whether or not it’s tabloids or somebody speculating a sure factor or individuals studying into your physique language, . You simply discover ways to talk with one another and also you’ll be on the identical web page with all the things occurring. … No one may ever put together you for what life is like after that. Like, you may have individuals let you know all you need, like, ‘Oh, watch for this, watch for this.’ However till you’re in it, you don’t actually get the complete magnitude of it.”
When Did Colton Underwood and Cassie Randolph Break Up?
Colton Underwood and Cassie Randolph revealed through Instagram in Could 2020 that they’d determined to name it quits.
“Colton and I’ve damaged up, however have determined to stay part of every others lives. With all that now we have gone by way of, now we have a particular bond that may all the time be there,” Randolph wrote on the time. “I like Colton very a lot and have an infinite quantity of respect for him. We now have each realized and grown a lot these previous couple years, and can all the time have one another’s again. At all times.”
Why Did Cassie Randolph Request a Restraining Order Towards Colton Underwood?
Following some public back-and-forth within the wake of their cut up, information broke in September 2020 that Cassie Randolph filed a restraining order in opposition to Colton Underwood, claiming he had planted a monitoring system in her automobile, harassed her through textual content message and confirmed up uninvited to her residence and her dad and mom’ home after their breakup.
The order was granted, forcing Underwood to remain at the very least 100 yards away from Randolph. He was additionally ordered to not contact her.
Two months later, Underwood revealed that the case had been settled privately, and the restraining order was dropped.
How Did Colton Underwood Deal with the Scandal?
Colton Underwood broke his silence about his private life when he got here out on Good Morning America in April 2021. He claimed that he was beforehand very a lot in love with Cassie Randolph, which brought on confusion and led to a tumultuous breakup.
“I’m sorry for any ache and emotional stress I brought on,” he mentioned. “I want that it wouldn’t have occurred the way in which that it did. I want that I had been brave sufficient to repair myself earlier than I broke anyone else.”
Later that 12 months, Underwood addressed the authorized drama once more on his Netflix docuseries, Coming Out Colton.
“I feel that (the restraining order) was kind of an enormous wake-up name. I’m unhappy that it even bought to that time to the place that needed to be my wake-up name, and me affecting different individuals in my life was kind of the second that I spotted I needed to come out,” he informed Us in December 2021. “Clearly, I want I’d have had the braveness to come back out with out having to be pushed.”
Randolph was requested to be a part of the sequence, however she declined.
One other Bachelor Nation love story has come to an finish. Colton Underwood and Cassie Randolph didn’t have the standard romance — and even the standard Bachelor timeline. Nonetheless, from the second they met on the season 23 Bachelor premiere, the pair had been related. Though their onscreen journey wasn’t a straightforward one (the fence leap!), they (…)
Has Cassie Randolph Mentioned Something Concerning the Authorized Drama?
Cassie Randolph, who has been married to Brighton Reinhardt since 2025, has remained largely tight-lipped about what occurred with Colton Underwood. She made a uncommon remark in March 2022 on Kaitlyn Bristowe’s “Off the Vine” podcast, saying, “I haven’t talked about it, so it’s actually laborious for me to speak about it in any respect, and even know the proper factor to say when addressing it. I really feel a lot stress when requested about it that I’d love to have the ability to be open and candid about issues, however I’m simply not there but. I’m positive I’ll someday need to communicate on it as a result of there’s only a lot there.”
Randolph additionally claimed that her ex didn’t give her a heads-up that he was planning to come back out on nationwide TV. “I discovered the identical method that everybody else did,” she recalled. “I used to be truly in Mexico on trip with pals. … However yeah, I discovered, I feel, by way of Snapchat on GMA. It was horrible. It was simply, like, a surprising form of feeling. ”
Later that 12 months, Randolph issued a message to Underwood.
“I’m very pleased that he’s … at peace with himself and never carrying that burden anymore, after all,” Randolph mentioned on an October 2022 episode of the “Ben and Ashley I Nearly Well-known” podcast. “It was a really, simply, total laborious time for me, so I really feel like there was only one factor after one other and I used to be simply extraordinarily overwhelmed with all the things occurring.”
Why Was Colton Underwood’s Previous 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 points with Cassie Randolph.
“I met with manufacturing. I met with Peacock. I used to be like, ‘I’m down to do that.’ As a result of this present is about technique. It’s concerning the recreation. It’s about traitors. It’s not private,” he defined to Vainness Honest in February 2026 about attempting to maintain the narrative off the present. “My solely ask is, like, if I do that, I don’t need individuals to carry up something exterior of the sport. I’ve a household now, proper? I’m … up to now previous what occurred six years in the past.”
Underwood addressed what occurred with Randolph on the reunion after not discussing it through the season.
“I feel what I can perceive from individuals viewing me again on tv, should you didn’t observe my story and what I went by way of, and also you watched me because the Bachelor in 2019, after which, hastily, you’re tuning in in 2026,” he mentioned. “I had an extremely troublesome couple of years, and I’ve grown, I’ve modified. I’ve put in a lot work into myself and to my household. I by no means actually thought the way in which that I’d present up and play Traitors could be linked to one of many darkest and most horrible moments of my life.”
Have Colton Underwood and Cassie Randolph Spoken For the reason that Restraining Order Was Dropped?
“I’ve no contact. If she ever did attain out or need to attain out, I’d be open to answering any questions that her or her household would have for me,” Colton Underwood informed Vainness Honest in February 2026. “That’s one thing I’ve all the time provided. I’m in no place to actually say far more than that or attain out. There’s been no a part of me that might. I’d all the time be up for it. It’s all on her phrases.”
Underwood mirrored on what led to the messy breakup.
“It was 2020. It was, as individuals bear in mind, COVID. I used to be absolutely satisfied that she was gonna be my final straight … like, I used to be going to need to both kill myself or come out. That’s simply transparently, like, the place my mindset was,” he elaborated. “I don’t know if that is the proper phrase, but it surely was considerably of the proper storm of me hitting all-time low, of me actually attempting to navigate, ‘Am I gonna kill myself or am I gonna come out?’ That’s simply the place I used to be at.”
Underwood, who’s now married to husband Jordan C. Brownadditionally revealed he was being blackmailed about his sexuality on the time and was “battling Xanax and prescription drugs.”
“It was a reasonably intense second in my life the place I made some actually, actually poor choices. The troublesome half now could be seeing the individuals who have quite a bit to say about what occurred six years in the past,” he famous. “It’s missing numerous the context of the place our world was at, but in addition the place I used to be at, the way of thinking that I used to be in.”
Underwood continued: “The pressures and the threats that I used to be going by way of. I’ll all the time take accountability. I’ll all the time personal errors that I made. However all the things that you just’re seeing on social media — these movies, these individuals who have quite a bit to say — just isn’t appropriate.”
If you happen to or somebody is experiencing home violence, please name the Nationwide Home Violence Hotline at 1-800-799-7233 for confidential assist. If you happen to or somebody is struggling or in disaster, assist is out there. Name or textual content 988 or chat at 988lifeline.org.