Colton Underwood Through the Years

Colton Underwood has been in the spotlight for many years, with his career beginning in the NFL — see photos

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.”

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.