The Evolution of Colton Underwood: From Professional Football to Reality TV and More

Colton Underwood has been open about his life with fans, from his football days to his time on Bachelor Nation.

Following his father's lead, Underwood played college football at Illinois State University. From 2014 to 2016, he had short stints with the San Diego Chargers, Philadelphia Eagles, and Oakland Raiders.

Although his football career was cut short due to an injury, Andrew East found love with athlete Aly Raisman. However, their relationship didn't last. He then appeared on The Bachelorette and later became the lead on The Bachelor season 23. Even though he didn't get engaged on the show, he did find love with Cassie Randolph, whom he dated until May 2020.

Nearly a year later, Underwood publicly came out as gay in an interview on Good Morning America.

During the interview, Underwood expressed his love for Randolph and acknowledged the emotional turmoil he experienced during their relationship. He apologized sincerely for any pain and stress he may have caused, expressing regret for the way things unfolded. He wished he had taken the time to work on himself before hurting anyone else.

Scroll down to see more about Underwood's journey.

Colton Underwood Through the Years

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

Colton Underwood has taken fans on a journey through various stages of his life, from his time playing football to his participation in Bachelor Nation.

Underwood continued his father's legacy by playing college football at Illinois State University. From 2014 to 2016, he had short stints with the San Diego Chargers, Philadelphia Eagles, and Oakland Raiders.

Despite his football dreams being cut short by an injury, Andrew East, a fellow football player, introduced him to athlete Aly Raisman, who became his first love. Following their breakup, he appeared on The Bachelorette and later starred in The Bachelor season 23. Although he didn't propose on the show, he found love with Cassie Randolph, whom he dated until May 2020.

Nearly one year later, Underwood revealed that he is gay in an interview on Good Morning America.

During the interview, Underwood expressed his love for his ex-girlfriend Randolph, admitting that he struggled internally while in the relationship. He apologized sincerely for any pain or emotional distress he may have caused, expressing regret for not addressing his own issues before hurting others.

Scroll through the gallery below for more on Underwood's journey.

Colton Underwood Through the Years

Credit: ABC; Shutterstock; ABC; Shutterstock

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

From his college football days at Illinois State University to his time in Bachelor Nation, Colton Underwood has been open about his life with his fans.

Following his father's lead, Underwood played college football at Illinois State University. He also had brief stints with the San Diego Chargers, Philadelphia Eagles, and Oakland Raiders between 2014 and 2016.

Although Andrew East's football career was cut short by an injury, he found love with athlete Aly Raisman. However, their relationship eventually ended. He then appeared on The Bachelorette and later became the lead on The Bachelor season 23. Although he didn't get engaged on the show, he did fall in love with Cassie Randolph, whom he dated until May 2020.

Nearly a year later, Colton Underwood came out as gay during an interview on Good Morning America.

During the interview, Underwood expressed his love for Randolph but found it difficult to accurately convey his emotions due to an internal struggle. He apologized sincerely for any pain and emotional distress he may have caused, expressing regret for the way things unfolded. He wished he had the courage to work on himself before hurting others.

Scroll down to see more about Underwood's journey.

NFL Career Colton Underwood Through the Years

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NFL Career

Underwood began his NFL career in May 2014 when he signed as an undrafted free agent with the San Diego Chargers. However, three months later, he was released from the team. Despite this setback, he was picked up by the Philadelphia Eagles practice squad the following month. Over the next few years, Underwood continued to move between teams, including a brief return to the Chargers. Unfortunately, in 2015, he was placed on the injured reserve list. Despite facing challenges, Underwood did not give up and signed with the Raiders practice squad later that year. He spent nearly eight months with the team before eventually being released.

Aly Raisman Relationship Colton Underwood Through the Years

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Aly Raisman Relationship

Underwood and the Olympian were in a relationship from August 2016 to April 2017. Sadly, Aly ended the relationship just two weeks after expressing her love for him for the first time. This came as a shock to Underwood, who was left feeling heartbroken. In his memoir, he described pulling over to the side of the road, feeling stunned and unable to believe what was happening. Aly mentioned feeling overwhelmed, confused, and needing a break. After their conversation, Underwood sat in his car and cried, feeling numb for days.

The Bachelorette Colton Underwood Through the Years

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'The Bachelorette'

In 2018, Colton Underwood joined the cast of The Bachelorette. During the casting process, he was advised by producers to watch the current season of The Bachelor and select someone he was interested in. Alongside Becca Kufrin, whom he would later compete for, he chose Tia Booth. Before filming for The Bachelorette started, Underwood and Booth started FaceTiming and went on a few dates. However, he then decided to go on The Bachelorette. Despite developing feelings for Kufrin, he ultimately finished in fourth place.

Bachelor in Paradise Colton Underwood Through the Years

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'Bachelor in Paradise'

Colton Underwood joined season 5 of Bachelor in Paradise and got back together with Booth in 2018. Unfortunately, their relationship didn't last long. Later, Underwood confessed that he only went on the show to improve his chances of becoming the Bachelor.

The Bachelor Colton Underwood Through the Years

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Rewritten Content:

'The Bachelor'

In January 2019, fans watched as Underwood's season of The Bachelor unfolded. One of the most memorable moments was when he famously jumped over a fence after Randolph left the show. Before the overnight dates, he decided to end things with the other contestants to try and win her back. The couple confirmed during the After the Final Rose special that they were officially in a relationship.

Writes Memoir Colton Underwood Through the Years

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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.

Messy Cassie Relationship Colton Underwood Through the Years

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Messy Cassie Relationship

Underwood and Randolph ended their relationship in May 2020 but initially remained friends. However, in September 2020, things took a turn when she obtained a restraining order against him, alleging that he had placed a tracking device on her car. Despite his denial of the accusations, they reached a private settlement, and the order was lifted in November 2020.

Coming Out Colton Underwood Through the Years

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Coming Out

In April 2021, Underwood revealed that he is gay during an interview on Good Morning America. He explained, "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." Underwood admitted to putting himself in difficult situations in an attempt to force himself to be straight.

Colton Underwood Through the Years

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Finding New Love

Five months after publicly revealing that he is gay, Underwood began dating political strategist Jordan C. Brown. Their relationship quickly blossomed, and they became engaged just one year later.

Underwood expressed his immense joy over the engagement, calling 2021 the most transformative year of his life. He shared with People magazine, "Starting off 2022 with my best friend, teammate, and now fiancé is truly a dream come true for me."

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

Colton Underwood Through the Years

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Dad to Be

Underwood shared in May 2024 that he and Brown were expecting their first child. He posted on Instagram a photo of their hands holding an ultrasound picture, announcing, "Our little boy is coming this fall."

In an interview with Men’s Health, Underwood discussed their surrogate journey. He mentioned, "Some people focus on physical traits like blue eyes and blond hair. For us, we value depth and coolness." Underwood emphasized the importance of love in raising their child, expressing his belief in nature over nurture. Their baby was scheduled to be born in October 2024.

Editor's P/S:

Colton Underwood's journey has been marked by both triumph and adversity. From his days as a college football star to his time in Bachelor Nation, he has navigated the ups and downs of life in the public eye. However, it was his decision to come out as gay that truly changed the course of his life. In an interview on Good Morning America, Underwood expressed the emotional turmoil he experienced while hiding his true self, and the regret he felt for the pain he caused others. His honesty and vulnerability inspired many, and his story continues to serve as a reminder of the importance of authenticity and self-acceptance.

Underwood's relationship with Jordan C. Brown has brought him a sense of peace and happiness. The couple's engagement and subsequent marriage are a testament to the transformative power of love. Their journey as expectant parents is another chapter in Underwood's life that is filled with joy and anticipation. His decision to become a father through surrogacy is a reflection of his dedication to creating a loving and supportive home for his child. As he prepares for this new chapter, Underwood's story continues to inspire others to embrace their true selves and live their lives to the fullest.