Colton Underwood's Relationship Journey: From Aly Raisman to Cassie Randolph and Beyond

Colton Underwood’s relationships have been in the spotlight both before and after he became a part of Bachelor Nation.

He quickly developed strong feelings for Olympian Aly Raisman after being introduced by a friend. In his 2020 memoir, The First Time: Finding Myself and Looking for Love on Reality TV, he described Aly as easy to talk to, open, funny, bright, honest, and curious. He found her laughter contagious and her smile captivating, feeling content just gazing at it without needing any further conversation.

After telling him she loved him, she decided to end their relationship through FaceTime.

Following his appearance on Becca Kufrin's season of The Bachelorette in 2018, Underwood became the lead on season 23 of The Bachelor in the next year. He found love with Cassie Randolph on the show, but their relationship ended messily 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:

Colton Underwood Dating History

Credit: Matt Baron/Shutterstock

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

Colton Underwood’s relationships made headlines before and after he joined Bachelor Nation.

Underwood quickly developed strong feelings for Olympian Aly Raisman after being introduced by a friend. In his 2020 memoir, he described her as easy to talk to, open, funny, bright, honest, and curious. He was captivated by her infectious laugh and her beautiful smile, which he could have admired all night without needing any further conversation.

Just two weeks after confessing her love for him, Raisman ended their relationship through a FaceTime call.

After appearing on The Bachelorette with Becca Kufrin in 2018, Underwood became the lead on season 23 of The Bachelor the next year. He eventually found love with Cassie Randolph on the show, but their relationship ended in a messy breakup in 2020.

In 2021, Underwood publicly came out as gay and started a relationship with his now-husband, Jordan C. Brown, in the same year.

Scroll through the gallery below to look back at his dating history:

Colton Underwood Dating History

Credit: Matt Baron/Shutterstock

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

Colton Underwood's relationships were a hot topic even before he became a part of Bachelor Nation.

He quickly developed feelings for Olympian Aly Raisman after being introduced by a friend. In his 2020 memoir, "The First Time: Finding Myself and Looking for Love on Reality TV," he described Aly as easy to talk to, open, funny, bright, honest, and curious. He couldn't help but admire her smile and wished he could just spend the night gazing at it without needing any further conversation.

Two weeks after confessing her love to him, she decided to end their relationship through a FaceTime call.

After appearing on Becca Kufrin's season of The Bachelorette in 2018, Underwood became the lead in season 23 of The Bachelor the next year. He found love with Cassie Randolph on the show, but their relationship ended in a messy breakup 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:

Aly Raisman Colton Underwood Dating History

Credit: Invision/AP/Shutterstock

Aly Raisman

Underwood's first love was the Olympian Aly Raisman. Their relationship started in 2016 when they were set up by Andrew East. He fell for her quickly and after just one month of dating, he confessed his love for her. Unfortunately, their love story came to an end in 2017 when Raisman decided to break up with him. It was a heartbreak for Underwood.

Savannah Chrisley and Colton Underwood Recall Going on a Date in 2017: ‘I Knew You Were Gay’

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Savannah Chrisley

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

When we first met, I had a feeling that you were gay. It was during the ACM Awards, right after my breakup with Luke Kennard. I was feeling pretty down, you know how it is after a breakup.

During an episode of her “Unlocked with Savannah Chrisley” podcast in 2023, Chrisley mentioned, “I knew it was you. 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 humorously responded, “When I say, ‘It’s not you, it’s me,’ I truly mean that. And obviously, I’ve proven that at this point.”

Tia Booth Colton Underwood Dating History

Credit: Courtesy of Tia Booth/Instagram

Tia Booth

During the casting process for The Bachelorette in late 2017, Underwood was asked about his interest in women from the current season of The Bachelor. He mentioned Kufrin, Booth, and Burnham. Underwood started talking to Booth through Instagram after that. They texted and FaceTimed a lot before finally meeting in person.

After being selected for The Bachelorette, Booth received a warning from his friend before his phone was confiscated. She jokingly said, "If you don’t win her heart, I’ll meet you in Paradise." Unfortunately, Kufrin did not pick Underwood, leading him to briefly reconnect with Booth on season 5 of Bachelor in Paradise. Eventually, they both decided to go their separate ways. Underwood later went on to become the Bachelor.

Becca Kufrin Colton Underwood Dating History

Credit: ABC/Paul Hebert

Becca Kufrin

Underwood appeared on The Bachelorette with Kufrin in May 2018. He developed feelings for her during the show but was eliminated in week eight, finishing in fourth place. Despite not ending up together, they stayed friends after the breakup.

Cassie Randolph Colton Underwood Dating History

Credit: Danny Moloshok/Invision/AP/Shutterstock

Cassie Randolph

The reality star developed strong feelings for Randolph during his time on The Bachelor in 2018. Despite her decision to leave the show early, he chose her over the other contestants and expressed his desire to be with her. They were in a relationship until May 2020. Initially, their breakup was friendly, but things took a turn when she accused him of tracking her car and filed a restraining order against him in September 2020. He denied the accusations. However, in November, he announced that they had resolved the issue privately, and she withdrew the restraining order.

Colton Underwood Dating History Jordan C Brown

Credit: Courtesy Colton Underwood/Instagram

Jordan C. Brown

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

That same month, the couple purchased a house in Sherman Oaks, California. In February 2022, the Bachelor Nation alum revealed his engagement to Brown.

"I couldn't be more thrilled! 2021 was truly a year of great change for me," Underwood shared with People in a statement. "Beginning 2022 with my closest companion, partner, and now future spouse is a dream come true that I never imagined could happen."

In May 2023, the couple exchanged vows in a beautiful ceremony in Napa Valley. Sharing photos from their special day on Instagram, they posted, "The Brown-Underwoods ❤️ May 13th 2023."

One year later, the couple shared the exciting news that they were expecting their first child. Underwood posted a picture on Instagram with Brown, holding an ultrasound photo, announcing, "Our little boy is coming this fall." In an interview with Men’s Health, Underwood disclosed that their surrogate was due in October.

Editor's P/S:

Colton Underwood's journey of love and self-discovery has been a captivating one. From his initial connection with Olympian Aly Raisman to his