Colton Underwood’s Dating History: Aly Raisman, Cassie Randolph and More

Credit: Matt Baron/Shutterstock

Colton Underwood's Dating History: Aly Raisman, Cassie Randolph and More

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: [podcast_block]

Credit: Matt Baron/Shutterstock

Colton Underwood's Dating History: Aly Raisman, Cassie Randolph and More

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: [podcast_block]

Credit: Invision/AP/Shutterstock

Aly Raisman

The Olympian was Underwood's first love, and he fell fast after they were set up by Andrew East in 2016. After one month of dating, he told her he loved her. He was heartbroken when she ended the relationship in 2017.

Credit: Shutterstock (2)

Savannah Chrisley

The twosome went to the ACM Awards in 2017 — but felt “no connection.”

“When we met the first time, I knew you were gay. Like, I knew it,” Chrisley said on an episode of her “Unlocked with Savannah Chrisley” podcast with Underwood in 2023. “It was the ACM Awards. …  It was after Luke Kennard and I broke up. I was like, 'All right, screw this.' You know how it goes. You go through a breakup.”

Underwood joked: “When I say, ‘It’s not you, it’s me,’ I truly mean that. And obviously, I’ve proven that at this point.”

Credit: Courtesy of Tia Booth/Instagram

Tia Booth

When Underwood started the casting process for The Bachelorette at the end of 2017, the production asked him which women on the current season (season 22 of The Bachelor) he was interested in. He answered Kufrin, Booth and Lauren Burnham and eventually, began chatting with Booth via Instagram. They spent time texting and FaceTiming non-stop before finally meeting.

After he was chosen for The Bachelorette, Booth was his last call before his phone was taken and she told him, "If you don’t end up with her, I’ll see your ass in Paradise." Kufrin did not choose Underwood and he briefly reunited with Booth on season 5 of Bachelor in Paradise before they decided to go their separate ways. (He went on to become the Bachelor.)

Credit: ABC/Paul Hebert

Becca Kufrin

Underwood made his reality TV debut during Kufrin's season of The Bachelorette, which debuted in May 2018. He fell for her during filming but was ultimately sent home during week eight, coming in fourth. The pair remained friends following their split.

Credit: Danny Moloshok/Invision/AP/Shutterstock

Cassie Randolph

The reality star fell hard for Randolph during his season of The Bachelor in 2018. After she chose to quit the show before the overnight dates, he sent home the remaining contestants and went to the speech pathologist's home and convinced her he wanted to be with her. They dated until May 2020. Although their breakup was amicable at first, she later accused him of placing a tracking device on her car and filed a restraining order against him in September 2020. He denied the allegations. In November, he revealed they settled the matter in private and she dropped the order.

Credit: Courtesy Colton Underwood/Instagram

Jordan C. Brown

In September 2021, Us confirmed that Underwood was dating Brown after they posted photos from a tropical getaway together. Three months later, Underwood made their relationship Instagram official in December 2021.

That same month, the couple bought a house in Sherman Oaks, California. In February 2022, the Bachelor Nation alum announced that he was engaged to Brown.

"I'm extremely happy! 2021 was the most transformative year of my life," Underwood told People in a statement at the time. "Starting 2022 off with my best friend, teammate and now fiancé is something I never thought was going to be possible."

In May 2023, the lovebirds tied the knot in a romantic ceremony in Napa Valley. “The Brown-Underwoods ❤️ May 13th 2023,” they wrote via Instagram at the time alongside photos from the happy day.