Colton Underwood’s relationships made headlines before and after he joined Bachelor Nation.
Underwood fell fast for Olympian Aly Raisman after being set up by a friend. “Aly was easy to talk to. She was open, funny, bright, honest, and inquisitive. She laughed easily and had a smile that I would’ve been happy to simply gaze at for the rest of the night, no further conversation necessary,” he wrote in his 2020 memoir, The First Time: Finding Myself and Looking for Love on Reality TV.
Two weeks after she told him she loved him, she ended the relationship over FaceTime.
After competing on Becca Kufrin’s season of The Bachelorette in 2018, Underwood went on to lead season 23 of The Bachelor the following year. He found love on the show with Cassie Randolph. They twosome had a very messy breakup when they called it quits in 2020.
Underwood came out as gay in 2021 and began dating his now-husband, Jordan C. Brown, that same year.
Scroll through the gallery below to look back at his dating history:
