Bachelor Nation first met the former NFL player when he competed on Becca Kufrin’s season 14 of The Bachelorette in 2018. After failing to form a lasting connection with the Minnesota native, Underwood moved on to season 5 of Bachelor in Paradise but again left the show single. He ultimately got his opportunity to hand out the roses when he starred as the Bachelor during season 23, which aired in 2019.
Underwood fell for Cassie Randolph on the show, and the two decided to date after the season wrapped instead of getting engaged. However, they announced their split in May 2020. Although they vowed to remain friends, things quickly turned messy.
Randolph was granted a restraining order against the Indiana native in September 2020 after she accused him of “stalking and harassing her.” He told Us Weekly in a November 2020 statement that his ex filed to dismiss the order after they reached “a private agreement to address any of Cassie’s concerns.”
Months after the drama, Underwood came out as gay in an April 2021 Good Morning America interview. “I’ve ran from myself for a long time, I’ve hated myself for a long time,” he said. “I’m gay. I came to terms with that earlier this year, and the next step in all of this was sort of letting people know. … I’m the happiest and healthiest I’ve ever been in my life. That means the world to me.”
The Coming Out Colton star hoped to form an “emotional connection” with a man in the future. “I’ve never allowed myself to,” he shared. “It’s never been, sort of, in my cards to let myself get there and I want to more than anything. … I’m looking for someone who can push me and challenge me in all the great ways.”
Us confirmed in September 2021 that Underwood is dating Brown. Three months later, the TV personality explained why his show Coming Out Colton did not include his relationship.
“I have been through that. I have done that,” he told Us of documenting his dating life. “Even going into the show, that was one of the conversations with the production company. … I’m not in a space right now to really, like, put myself out there like that. I had a lot of self-discovery to do.”
Underwood has not ruled out documenting his romance with Brown on a reality show, though. “I don’t want to speak in definitives right now because as I learned, I’m growing and I want to give myself space to really explore new things at the moment. I’ve definitely drawn boundaries on that. Having a public relationship, for me, was not healthy,” he said. “I just think right now I’m really sort of protecting and guarding what I have.”
Scroll through the gallery below to revisit the couple’s relationship timeline: