Quite the journey. Before Colton Underwood entered Bachelor Nation, he stepped into the limelight with his first relationship. In 2016, he made multiple public appearances with Olympian Aly Raisman.
The pair were set up by a friend and he fell fast, as chronicled in his 2020 memoir, The First Time: Finding Myself and Looking for Love on Reality TV.
“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,” the Indiana native wrote, opening up about the romance publicly for the first time. “It was very late when I dropped her back at her hotel, and when I said I’d had a great time, I meant it. Later that night, Aly texted me a thank-you. Neither of us had expected to get on as well as we did. For a first date, it couldn’t have gone better.”
Two weeks after she told him she loved him, she ended the relationship over FaceTime.
“I pulled over to the side of the road, stunned and unable to comprehend this was happening,” the athlete shared in his memoir. “Aly said she felt overwhelmed, confused, and in need of a break. Afterward, I sat in my car and cried. I was numb for days.”
The relationship with the gymnast was the first of Underwood’s many public relationships. The former NFL player joined Bachelor Nation in 2018, first appearing on Becca Kufrin‘s season of The Bachelorette.
However, he had already been in contact with someone else from Bachelor Nation, spending time in Los Angeles with Tia Booth before vying for Kufrin’s heart on season 14. After leaving The Bachelorette solo and making a brief appearance on Bachelor in Paradise, Underwood became the Bachelor in 2018 and found love once again with Cassie Randolph.
The pair split in May 2020. Nearly one year later, the Colton Underwood Legacy Foundation founder came out as gay during an interview on Good Morning America.
“This year’s been a lot for a lot of people and it’s probably made a lot of people look at themselves in the year and figure out who they are,” he shared at the time. “I’ve ran from myself for a long time, I’ve hated myself for a long time. 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.”
Later that year, Underwood sparked romance rumors with Jordan C. Brown after they were spotted enjoying a tropical getaway together. They made their relationship Instagram official in December 2021.
Two months later, Underwood confirmed that they were engaged.
Scroll through the gallery below to look back at his dating history: