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.