Colton Underwood Through The Years: Photos - Us Weekly

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Colton Underwood Through the Years: From the NFL to 'The Bachelor' and Beyond

From playing football to joining Bachelor Nation, Colton Underwood has shared all aspects of his life with fans over the years. Underwood followed in his father’s footsteps by playing college football at Illinois State University. Between 2014 and 2016, he was briefly signed to the San Diego Chargers, the Philadelphia Eagles and the Oakland Raiders. Although his football career didn't pan out due to an injury, football player Andrew East set him up with athlete Aly Raisman, who ended up being his first love. After their relationship fell through, he went on to compete on The Bachelorette and became the lead of The Bachelor season 23. He didn’t get engaged on the show but did fall in love with Cassie Randolph, whom he dated until May 2020. Nearly one year later, Underwood came out as gay during an interview on Good Morning America. “I loved everything about [Randolph] and it’s hard for me to articulate exactly what my emotions were in going through that relationship with her was because I obviously had an internal fight going on,” Underwood said during the interview, noting that he was in love with his ex-girlfriend. “I would just say that I’m sorry from the bottom of my heart. I’m sorry for any pain and emotional stress I caused. I wish that it wouldn’t have happened the way that it did. I wish that I had been courageous enough to fix myself before I broke anybody else." Scroll through the gallery below for more on Underwood's journey.

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NFL Career

In May 2014, Underwood was signed as an undrafted free agent by the San Diego Chargers. Three months later he was dropped, only to be picked up the following month by the Philadelphia Eagles practice squad. He continued to bounce around — even briefly returning to the Chargers — and eventually was placed on the injured reserve list in 2015. He tried once again to play and was signed to the Raiders practice squad in 2015, where he remained for nearly eight months before being dropped.

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Aly Raisman Relationship

Underwood dated the Olympian between August 2016 to April 2017, and he was heartbroken when she ended the relationship two weeks after saying "I love you" for the first time. “I pulled over to the side of the road, stunned and unable to comprehend this was happening,” he wrote 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."

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'The Bachelorette'

In 2018, Underwood was cast on The Bachelorette. While in casting, producers told him to watch the current season of The Bachelor and pick out who he liked. Along with Becca Kufrin, who he'd end up competing for, he said Tia Booth. Before The Bachelorette began filming, Booth and Underwood began FaceTiming and eventually met up for a few dates. However, he then went on The Bachelorette. Although he developed feelings for Kufrin, he came in fourth place.

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'Bachelor in Paradise'

Underwood went on season 5 of Bachelor in Paradise and rekindled his relationship with Booth in 2018. It was short-lived, and he later admitted he only went on because it would help his chances of becoming the Bachelor.

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'The Bachelor'

In January 2019, Underwood's season of The Bachelor aired and followed his journey — including his famous fence jump, which happened after Randolph quit the show. Before the overnight dates, he broke up with the remaining cast members and went to find her. The pair revealed during the After the Final Rose special that they were dating.

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Writes Memoir

In March 2020, Underwood revealed all about his time in Bachelor Nation, his relationship with his parents, questions about his sexuality and his virginity in a memoir.

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Messy Cassie Relationship

Underwood and Randolph split in May 2020 and remained friends, at first. In September 2020, she was granted a restraining order against her ex and claimed that he placed a tracking device on her car. He denied the claims, and they ultimately settled the case in private. The order was dropped in November 2020.

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Coming Out

In April 2021, Underwood came out as gay during a Good Morning America interview. “I could never give anybody a good enough answer about why I was a virgin. The truth is I was ‘the virgin Bachelor’ because I was gay, and I didn’t know how to handle that,” he told Robin Roberts at the time. “I put myself in really bad situations on purpose. I put myself in these situations so I could try to force myself to be straight.”

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Finding New Love

Five months after Underwood came out as gay, Us confirmed that the Bachelor Nation star was dating political strategist Jordan C. Brown. They got engaged one year later.

“I’m extremely happy! 2021 was the most transformative year of my life,” Underwood told People of his engagement. “Starting 2022 off with my best friend, teammate and now fiancé is something I never thought was going to be possible.”

The couple got engaged in early 2022 and tied the knot in Napa Valley, California, in May 2023.

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Dad to Be

Underwood announced in May 2024 that he and Brown were expecting their first child. “Our little boy is coming this fall 💙,” he captioned an Instagram photo of their hands holding a picture of their son’s ultrasound.

Underwood opened up about his and Brown’s surrogate journey in an interview with Men’s Health. “Some people want blue eyes and blond hair,” he said of the surrogate selection process. “We want somebody deep and cool. I believe in nature vs. nurture. So give us the basics and we can show this kid love.” He also revealed that their baby was expected to arrive in October 2024.

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