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

Credit: ABC; Shutterstock; ABC; Shutterstock

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

From football to finding love! Colton Underwood has let fans into a lot of his life over the years. Before stepping into the spotlight, Underwood grew up in Indianapolis, Indiana. His family moved to Illinois when he was 5. In 2013, he moved again, this time to Colorado, following his parents' divorce. While attending Illinois State University, he followed his father's footsteps and played college football for the Illinois State Redbirds. 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. “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," he shared about their first date in his book, The First Time: Finding Myself and Looking for Love on Reality TV, which was released in March 2020. "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.” [sendtonews type="float" key="AM9R60uFDc-2839741-14453"] Although the pair didn't last, he was thankful for the time they had together — and it prepared him for his future relationships. Underwood went on to appear on The Bachelorette and Bachelor in Paradise before becoming the Bachelor in 2018. While he didn't get engaged, he fell in love during his time on the show and dated Cassie Randolph until May 2020 when they split. 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. [podcast_block]

Credit: ABC; Shutterstock; ABC; Shutterstock

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

From football to finding love! Colton Underwood has let fans into a lot of his life over the years. Before stepping into the spotlight, Underwood grew up in Indianapolis, Indiana. His family moved to Illinois when he was 5. In 2013, he moved again, this time to Colorado, following his parents' divorce. While attending Illinois State University, he followed his father's footsteps and played college football for the Illinois State Redbirds. 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. “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," he shared about their first date in his book, The First Time: Finding Myself and Looking for Love on Reality TV, which was released in March 2020. "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.” [sendtonews type="float" key="AM9R60uFDc-2839741-14453"] Although the pair didn't last, he was thankful for the time they had together — and it prepared him for his future relationships. Underwood went on to appear on The Bachelorette and Bachelor in Paradise before becoming the Bachelor in 2018. While he didn't get engaged, he fell in love during his time on the show and dated Cassie Randolph until May 2020 when they split. 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. [podcast_block]

Credit: Rick Scuteri/AP/Shutterstock

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.

Credit: Rich Fury/Invision/AP/Shutterstock

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."

Credit: ABC/Paul Hebert

'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.

Credit: ABC/Craig Sjodin

'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.

Credit: ABC/Craig Sjodin

'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.

Credit: Jordan Strauss/Invision/AP/Shutterstock

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.

Credit: Broadimage/Shutterstock

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.

Credit: GMA

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.”