18 hours Ago By Johnni Macke
Kaitlyn Bristowe is a girl’s girl, so she made sure to check in on pal Cassie Randolph before working with her ex-boyfriend Colton Underwood . Bristowe, 39, shared on the Wednesday, April 2, episode of her “ Off the Vine ” podcast that her previously teased project with Underwood, 33, would soon be revealed. She also noted that Underwood’s ex Randolph, 29, who means a lot to Bristowe, had signed off on their collaboration.
“This is a very honest podcast for me. I want to have a lot of integrity with it,” Bristowe explained, pointing out, “I am friends with Cassie, and I know a lot of stuff went down between Colton and Cassie.” The former Bachelorette shared that she’s had “many conversations” with Underwood about “how he feels and what he has done wrong,” some of which pertains to Randolph.
Related: 'Bachelor' Alums Who Came Out As Members of the LGBT+ Community Bristowe went on to say Underwood, who is now married to Jordan C. Brown , is not a mean-spirited person. “He is an actual golden retriever who is so happy in life right now and was so lost at the time,” she continued, referring to Underwood dating Randolph while internally dealing with his sexuality.
(Underwood publicly came out as gay in April 2021, nearly one year after he and Randolph called it quits.) Bristowe told her listeners that she took into account how Randolph might feel about her spending time with Underwood after their complicated past. Related: Colton Underwood Through the Years “When I was getting to work with Colton, it was very important to me to reach out to Cassie and have the conversation with her,” Bristowe recalled, revealing that Randolph was “very gracious and grateful” about everything.
Once Bristowe had Randolph’s OK, she said she “got to move forward” with her and Underwood’s project. When it comes to what the collaboration is, Bristowe teased more details will be available shortly. “For the love of God! I wish this is something where I’m like, ‘How can I still not talk about it?’” the reality star said on the podcast, explaining that she filmed a special something with Underwood back in September 2024.
“I would say hopefully announcing in the next few weeks,” she added. Fans met Underwood during season 14 of The Bachelorette while he was vying for Becca Kufrin ’s heart. He was eliminated after hometown dates but later starred on season 5 of Bachelor in Paradise .
Underwood eventually became the season 23 lead on The Bachelor , where he picked Randolph as his final rose during the 2019 finale. (He famously jumped a fence after Randolph revealed she wanted to leave the show before its end.) The pair didn’t get engaged but they did date for two years before calling it quits in May 2020.
News broke in September 2020 that Randolph filed a restraining order against Underwood, claiming he planted a tracker on her car and was harassing her. Two months later, she dropped the restraining order, and the exes settled their case in private. After Underwood publicly revealed he is gay in April 2021, he apologized to Randolph , claiming he loved her very much when they were together.
“I’m sorry for any pain and emotional stress I caused,” he said on Good Morning America . “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.
” The following year, Randolph said she was “very happy” that Underwood was “at peace with himself” and no longer “carrying that burden.” She confessed on an October 2022 episode of the “Almost Famous” podcast that their split and his coming out journey was “a very overall hard time” for her. Related: Kaitlyn Bristowe’s Dating History: Bachelor Romances, Engagements and More Both Randolph and Underwood have since moved on romantically.
Underwood married Brown, 42, in May 2023 and they welcomed their first child, son Bishop , via surrogate in September 2024. Thank You! You have successfully subscribed. By signing up, I agree to the Terms and Privacy Policy and to receive emails from Us Weekly Check our latest news in Google News Check our latest news in Apple News Randolph, meanwhile, got engaged to Brighton Reinhardt in November 2024 after four years of dating.
Bristowe, for her part, has been part of Bachelor Nation since season 19 of The Bachelor . She became the Bachelorette during season 11, which resulted in an engagement to Shawn Booth . The pair called it quits in November 2018.
The Canada native moved on with another Bachelor Nation favorite Jason Tartick in 2019 and they got engaged in May 2021. Bristowe and Tartick, 36, split in August 2023..
