The Transformation Of Colton Underwood From Childhood To 29 Years Old

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Colton Underwood's journey has taken him from football to finding love and everything in between. The athlete-turned-reality star has experienced a lot throughout the last few years, but it's all led him to exactly where he's meant to be. Colton's story begins in Indianapolis, Indiana, where he was raised after moving to the midwestern state at the age of 5.

The TV personality — who was born on January 26, 1992 — was brought up by his parents, Scott Underwood and Donna Underwood, alongside his younger brother, Connor Underwood. Colton lived in Indianapolis through his teenage years, and when it was time for college, he attended Illinois State University, where he was recruited to play football for the Illinois State Redbirds, per Us Weekly.

Upon graduation, he was briefly signed to the San Diego Chargers, the Philadelphia Eagles, and the Oakland Raiders between 2014 and 2016. However, he struggled with a "serious shoulder issue" that ultimately resulted in an injury that led to his retirement in 2015, he told the Journal Star (via CheatSheet). Following his retirement, he created The Colton Underwood Legacy Foundation, a non-profit organization that "raises funds to provide equipment and resources for people of all ages living with cystic fibrosis," per the website. Since then, Colton has been juggling his philanthropic efforts while paving a career as a reality star and social media influencer. To find out how Colton's journey led him to "The Bachelor" and beyond, keep scrolling to see his ultimate transformation. 

Throughout his childhood, Colton Underwood struggled with bullies and self-love

Colton Underwood's confidence is off the charts these days, but that wasn't always the case for the former ABC personality. Like many other kids, Colton struggled with self-image and acceptance, revealing he was known as "the fat kid" at his Christian school growing up. The Indiana native has been extremely honest about his childhood experiences, opening up for one of the first times during the premiere of his "The Bachelor" season in January 2019.

"Grade school Colton would probably be really shy and timid at the fact that he was just named the Bachelor," he said on the show (via Romper). "I grew up in a pretty conservative environment. I was at a Christian school, and I was always like the fat, chunky, awkward, weird kid. I didn't have girlfriends. I wanted to fit in so bad, but I felt very alone. A lot of days, I didn't want to go to school."

The former professional football player later told People in March 2020 he was also called a list of cruel terms as a kid, including "fatso, four eyes, and four lips, because I used to lick my lips, so I would constantly have a red ring around them." He added, "I was a little heavy, and that, combined with being socially awkward, led to a really hard time. I didn't believe in myself. And I was super insecure."

Colton Underwood's love from his family supported him through his teen years

As he aged into his adolescence, Colton Underwood was a boy trying to find himself. Though he dealt with bullying and insecurities into his teenage years, he had the love of his family, especially mom Donna Underwood and dad Scott Underwood. "My mom and I have a great relationship," he gushed during his hometown date during Becca Kufrin's season of "The Bachelorette" in August 2018 (via Bachelor Nation YouTube). "I can tell my mom anything."

As for his father, Colton described their bond as a "coach-player relationship" because he grew up playing football with his dad as his mentor. Regardless, Colton credited his parents for giving him unconditional love throughout every step of his life. "I lucky ... I'm fortunate to have a mother and father [who] care so much about me," he said on the ABC reality series.

It's apparent how grateful Colton is for his parents, as he's publicly praised Donna and Scott in the past on his recently-wiped Instagram account. "Thanks for everything you do for me and all of the support over the years," the former San Diego Chargers player once wrote alongside a pic with his mom, via Distractify. Not only have Scott and Donna supported Colton through his tumultuous teenage years, but they were also by his side when it was time to start dating and becoming an adult. 

Colton Underwood didn't need 'The Bachelor' to fall for Aly Raisman

Colton Underwood fell in love for the first time with Olympian Aly Raisman. The TV hunk and the athlete became a couple in August 2016 after Colton asked her out through a video from Yahoo! Sports.

The pair went on a first date in Denver, and they keep their relationship on the down-low for three months until making their public debut at the Sports Illustrated Sportsperson of the Year Ceremony in December of that year, per People. In his book titled "The First Time: Finding Myself and Looking for Love on Reality TV," released in March 2020, Colton recalled their first date, saying it "couldn't have gone better."

"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," he penned (via Us Weekly). "Neither of us had expected to get on as well as we did." Sadly, their relationship ended two weeks after they said "I love you" for the first time in April 2017. Colton remembered how he "sat in my car and cried" when he and Aly called it quits after eight months. "I pulled over to the side of the road, stunned and unable to comprehend this was happening," he wrote in his memoir (via Us Weekly). "Aly said she felt overwhelmed, confused, and in need of a break. Afterward ... I was numb for days."

Colton Underwood made his debut on the ABC dating reality series

Following his split with Aly Raisman, it took a lot for Colton Underwood to overcome the "really tough" breakup. The former footballer said he considers his split with Aly to be the "worst" heartache he's ever experienced during an appearance on the "LadyGang" podcast in January 2019 (via Refinery29). However, he got a second chance at love when he was cast on Season 14 of "The Bachelorette," which ran from May to August 2018.

Colton vied for Becca Kufrin's heart, but he came up short and was sent home just one week before fantasy suite dates. However, his journey led to "Bachelor in Paradise," and ultimately, the starring role on Season 23 of "The Bachelor." The series aired from January to March 2019 and followed Colton along as he dated 30 women (via ABC).

The heartthrob's journey on the reality show is memorable for more reasons than just his famous fence jump — which was the result of frontrunner Cassie Randolph quitting the show. Because Colton was preparing to choose Cassie by the end of the season, he broke up with the remaining cast members prior to the overnight dates and followed after the California native. Though fans were unsure of the status of their relationship, Colton and Cassie revealed they were dating during the After the Final Rose following the conclusion of the season, per Us Weekly. From there, their romance blossomed (at first, at least). 

Colton Underwood pursued a relationship with Cassie Randolph

The beginning of Colton Underwood's relationship with Cassie Randolph wasn't the smoothest, but the two were dedicated to pursuing their romance. Though it was a "little bit of a struggle at first" to acclimate to having their love story in the spotlight, Cassie opened up about making it work after filming wrapped. "It was a little bit of a struggle at first, I think — like adjusting to everything," the speech pathologist told Us Weekly in October 2019. "But I feel like now we've kind of gotten used to it and learned to balance everything a lot more."

After the show, Colton relocated to California to be closer to Cassie. But just months later, the pair revealed via Instagram posts that they were going their separate ways in May 2020. "Colton and I have broken up," Cassie wrote (via Life & Style). "I love Colton very much and have an enormous amount of respect for him. We have both learned and grown so much these past couple years, and will always have each other's back. Always."

The two "decided to remain a part of each other's lives" at first, Cassie said in the breakup announcement. But in September 2020, she was granted a restraining order against Colton, claiming he placed a tracking device on her car, People reported. Colton denied the claims, and after settling in private, Cassie dropped the restraining order in November, per Us Weekly.

Colton Underwood found the courage to come out as gay

Six months after Colton Underwood made headlines for his messy breakup with Cassie Randolph, the Illinois State University alum entered a new journey of his life. After years of being questioned for his sexuality, in addition to the hot topic of his virginity on "The Bachelor," Colton courageously came out as gay during an interview on Good Morning America in April 2021.

"I've ran from myself for a long time. I've hated myself for a long time," he candidly told host Robin Roberts. "And I'm gay. And I came to terms with that earlier this year and have been processing it. And the next step in all of this was sort of letting people know." The "First Time" author said it was a long road getting to this point, admitting that at one time he "would've rather died" than tell the world the truth about his sexuality.

"There was a moment in L.A. that I woke up, and I didn't think I was gonna wake up. I didn't have the intentions of waking up. And I did," he recalled, adding that his "suicidal thoughts" ultimately forced him to "take back control" of his life. "If I had to go back and give anybody advice, I mean, 'you're gonna get through it' is what I would tell myself. Keep fighting for you. Keep choosing you every morning. And when the time's ready or when the time's right and you're ready, do it on your own time."

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

Colton Underwood is living his truth and embracing the future

There's been an obvious glow about Colton Underwood since he came out as gay. Whether he's boasting a big smile with his dog, Zooka, on Instagram or dancing with his friends on TikTok, it's apparent the star is at the happiest point in his life. Though Colton is excited for what the future has in store, he's reflected on his wrongdoings in the past and has acknowledged how he's affected others, especially ex Cassie Randolph.

"I never want people to think that I'm coming out to change the narrative, or to brush over and not take responsibility for my actions, and now that I have this gay life that I don't have to address my past as a straight man," he said during an interview with Variety in May 2021. "Controlling situations to try to grasp at any part of the straight fantasy that I was trying to live out was so wrong."

Fans will learn more about Colton's journey in an upcoming Netflix documentary, which is expected to premiere in fall 2021, per People. In the Variety feature, Colton's dad, Scott Underwood, expressed how proud he is of his son. "If it just helps a few young men and women come out and be proud of themselves and understand that all parents aren't going to be upset, it can save lives," Scott shared. While he's been through a lot, it sounds like Colton's real journey is just getting started.