Bachelor Nation first met the former NFL player when he competed on Becca Kufrin’s season 14 of The Bachelorette in 2018 before moving on to season 5 of Bachelor in Paradise. After leaving both shows 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. They ultimately split in May 2020, one year before Underwood came out as gay in an April 2021 Good Morning America interview.
Us Weekly confirmed in September 2021 that Underwood was dating Brown. Underwood and the political strategist got married in May 2023.
Scroll through the gallery below to revisit the couple’s relationship timeline: