Coming Out Colton follows Underwood as he embraces “his place in the LGBTQ community” and addresses his past, including his at-times-ugly breakup with ex-girlfriend Cassie Randolph, who he met on his season of The Bachelor. (She sought a restraining order against him after their split.) “I think there’s a real fear for me that people are going to say that I’m coming out to try to save my image and that I’m coming out to bury the drama that I had with Cassie,” Underwood says in the series, according to Page Six. However, “that’s the furthest thing from the truth,” Underwood declared. “If anything, the reason I’m coming out is because I’m ashamed and I’m sort of mortified of what got me to this position in the first place. I knew that I couldn’t hide it anymore because I didn’t want to affect or harm anybody else in my life.” Now that Coming Out Colton has premiered on Netflix, take a look back at Colton Underwood’s relationship with Cassie Randolph, plus some of the other famous faces he was once linked to.
How did Colton Underwood and Cassie Randolph meet?
The former couple met on Season 23 of The Bachelor, which premiered in January 2019.
Were Colton Underwood and Cassie Randolph ever engaged?
Underwood’s season did not end with a proposal. Randolph decided to leave the ABC show during their fantasy suite date in Portugal. “I love you so much, like so much, but I couldn’t after today, like I’m not in love,” she told Underwood. “I don’t know why after today, I’m not… I feel like I’m having doubts about it, and I don’t know.” Randolph explained that she was not leaving because she didn’t care about Underwood, but rather she said, “I don’t know if I can get there with you.” “I don’t care if you’re about to leave, I’m not gonna to stop fighting for you,” he told her. She said in response, “I want you to be with someone who’s like insanely in love with you. The thought… I’m not sure if I can get there… absolutely terrifies me and I can’t be here because of it. I can’t. I can’t. I can’t do that to you.”
What happened after Colton jumped the fence?
Underwood famously jumped a fence after Randolph’s exit and later decided to send the remaining two contestants, Tayshia Adams and Hannah Godwin, home. With the other women gone, the Season 23 lead went to Randolph’s hotel room to ask for a second chance. “I’m not sitting here asking for marriage at the end of this, I’m sitting here asking for a second chance to take it day by day and figure it out,” he said. With Randolph back in, the pair went on to meet Underwood’s family and have a fantasy suite date, during which she told the former football player that she wanted “to be all in.” Although the season didn’t end with an engagement, Underwood did hand out his final rose to Cassie (in front of then-host Chris Harrison and a live audience). “I know we started this with 30 roses, and I’m looking forward to spending a lifetime of happiness with you,” he said.
When did Colton and Cassie break up?
The TV stars announced in May 2020 that they were ending their relationship. “It’s been a crazy few months to say the least, Cass and I have been doing a lot of self-reflecting,” Underwood said, per E! Online. “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.” Although they decided to split, Randolph noted in her announcement that she and Underwood had “decided to remain a part of each other’s lives.” She continued, “With all that we have gone through, we have a special bond that will always be there. 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.”
What happened after Colton Underwood and Cassie Randolph ended their relationship?
Months after their split, Randolph filed for a restraining order against Underwood. According to court documents obtained by TMZ, Randolph claimed that her ex had been stalking and harassing her with unsettling text messages and that he planted a tracking device on her car. She also claimed that Underwood had been showing up uninvited to her apartment, as well as her parents’ home. It was reported in November 2020 that Randolph was dropping the restraining order. “Today, Cassie asked the court to dismiss the temporary restraining order against me. The two of us were able to reach a private agreement to address any of Cassie’s concerns,” Underwood said in a statement to PEOPLE. “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.” The Coming Out Colton star admits in his new Netflix series that he held on to their “relationship out of fear of being a gay man.” He said (via Page Six), “I did things that were messed up. I was paranoid. I was scared. I was terrified of myself. I was terrified of who I was going to become.”
When did Colton Underwood come out as gay?
Less than a year after his split from Randolph, Underwood came out as gay. “I’ve ran from myself for a long time. I’ve hated myself for a long time,” he confessed in an interview with Good Morning America’s Robin Roberts in April 2021. “And I’m gay. And I came to terms with that earlier this year and have been processing it. And the next step in all of this was sort of letting people know. Still nervous but yeah, it’s been a journey for sure.” https://m.youtube.com/watch?v=e4essSCicV8
What did Cassie Randolph say after Colton Underwood came out?
Randolph first broke her silence with a post on her Instagram Story thanking “everyone for all the kind comments and messages.” She added, “It means so much.” Randolph later addressed her ex coming as gay in a vlog on her YouTube channel. “Regarding the topic in the media that brought my name up this week,” she said, “I just wanted to let you know that I’m not gonna be further discussing it or commenting on it for now. There’s a lot of layers to it and I just feel like the best thing for me at this time is to move forward and just focus on going forward. So, If I do decide in the future to say anything or make a comment at all, you guys will be the first to know.”
Who else has Colton dated?
Becca Kufrin
The Legacy Foundation founder was first introduced to Bachelor Nation as a contestant on Becca Kufrin’s season of The Bachelorette (Season 14) in 2018. Underwood, who made it to the final four, was sent home after hometowns.
Tia Booth
Underwood has also been linked to another Bachelor Nation alum: Tia Booth, who competed with Kufrin on Arie Luyendyk Jr.’s season of The Bachelor. “I went to casting weekend for The Bachelorette and after leaving they said, ‘Hey, we’re releasing our girls this weekend. Take a look at them, let us know your top three.’ So I sent my top in three in, which between all three of us was Lauren [Burnham], Becca and Tia. Those were the girls, just off of their head shots. It’s very shallow, just off of physical appearance right off the bat,” Colton previously shared on Ben Higgins and Ashley Iaconetti’s podcast (via Us Weekly). “So I sent those back to the casting and I actually followed all three on Instagram and Tia followed me back. I wasn’t expecting that and I was pretty shy and I wasn’t going to DM her, it just is what is. I was watching Stranger Things about a week later and I put it on my Story and she [direct messaged] me and commented on Stranger Things. So this all started off of her [direct messaging] me about El from Stranger Things and we casually started talking, exchanged numbers, FaceTimed, and the second day that I talked to her, I actually disclosed to her that I was a finalist for the show and I was probably going on the show.” The pair ended up meeting up and had a “great weekend” together. “We went hiking at Runyon Canyon with rescue puppies and we went out to a steak dinner … It was a great date, great weekend, but I just left there knowing that she’s going back to Arkansas and I’m going back to Denver,” he said. “We had somewhat of a spark, somewhat of a connection, but there just wasn’t enough for me to say, ‘Hey, this is my person. I’m closing all my options out.’” While on The Bachelorette, Underwood told Kufrin that he had previously “had a relationship with Tia.” He admitted, “We had a weekend together, we had a good time, but for me, the timing wasn’t right to grow what was a spark into a flame. If my feelings were strong enough, I wouldn’t have come on this.” The Bachelorette alum and Booth reunited in Season 5 of Bachelor in Paradise. Though in the end, Underwood decided to break up with Booth and leave Paradise. It was announced that year that Underwood would be the next Bachelor. Despite things not working out between them, Booth has shown her support for Underwood in the past. After her ex came out as gay in 2021, she wrote on her Instagram Story, “@coltonunderwood knows how I feel. Love who you wanna love. There’s my statement. I am my own PR team gtg bye.”
Lucy Hale
In July 2020, a couple months after his split from Randolph, Underwood “casually dated” Pretty Little Liars star LucyHale. They were first spotted on a hike together in L.A. and apparently went on a few dates after that. TMZ claimed that before she got together with Underwood, Hale once said that Underwood “would make a good Bachelor because he’s ‘wholesome,’ a ‘good guy’ and ‘beautiful to watch.’” After Underwood came out, Hale praised him by writing on her Instagram Story, “I’m really, really happy for you @coltonunderwood. You deserve to be seen, heard, and accepted for exactly who you are. Brave, bold moves and I’m HERE FOR IT.”
Aly Raisman
Prior to joining the Bachelor franchise, Underwood dated Olympian Aly Raisman. The reality star has referred to the Olympic medalist as his “first love.” The pair, who were introduced by football player Andrew East, started dating in late 2016 and split in June 2017. “While it was confusing and hard in the beginning, it also taught me a lot about myself—what I need, what I want, what I can do better in a relationship,” Underwood said on a 2019 episode of the LadyGang podcast (via PEOPLE). “It was a big step for me. It was really tough.” Coming Out Colton is available to stream now on Netflix. Next, facts every Bachelor Nation fan should know!
