Inside Colton Underwood's' Dramatic Pre-Bachelor Journey

A healthy dose of humility is a good look on any Bachelor. Viewers would like to believe the show’s leads can maintain a humble nature even when a slew of polished, attractive women are literally competing for their time and affection, making moves to “steal them away” whenever an opportunity presents. 

And Colton Underwood would be the first to admit he wasn’t formed into being as a 6-foot-3 former pro football player with perfect abs just begging for nonstop shower sequences. “Grade school Colton probably would be really shy and timid by the fact that he was just named the Bachelor,” he shared on the January 2019 premiere of ABC’s beloved love hunt. “I was at a Christian school and I was always, like, the fat, chunky, awkward weird kid.” 

While the Indianapolis native had a bit of an ugly duckling emerging into a swan transformation when he discovered his football skills at Illinois’ Washington Community High School, ditched his bottom retainer and found a way to clear up his skin, before then there were a lot of days he wished he could call out sick, often struggling to fit in with the other kids. And romantic prospects were certainly out of the question: “I didn’t have girlfriends.”  

That is until he courted some 30 potential wives last year, charming his way through a mix of professional dancers, models, realtors and so very many pageant queens in the hopes of crowning one Mrs. Underwood. And while he did a fine job of decisively handing out the roses (see: his strong as ever relationship with Cassie Randolph, the woman he was so sure about he risked ending up alone), before meeting the woman he’s dubbed his “future wife”, he was admittedly a bit of an amateur in the love department. 

Did you hear that he was actually a virgin?

Christopher Polk/E! Entertainment/NBCU Photo Bank via Getty Images

Before taking on the mantle as the franchise’s 23rd star, the 28-year-old had just a handful of steady relationships—two of which were born from the series itself. That inexperience, he reveals in his just-released book, The First Time, led to a lot of questions about his sexuality. “It was one of those things where you hear something so often, you start believing it,” he wrote. “I thought, maybe I am gay. The captain of the football team should be having sex and drinking, right? But I wasn’t.”

By the time he got the nod to helm the successful love hunt, though, he was sure about who he was. Yes, he heard the rumors as his season premiered, “They’d say, ‘he’s gay, he’s hiding it.’ No. But I’ve been there, done that now,” he shared. 


At that point, the athlete turned philanthropist was used to his journey for love playing out in the public sphere.  

Following brief stints with the San Diego Chargers and the Philadelphia Eagles, the tight end got his first brush with fame thanks to his Oakland Raiders teammate Andrew East. In August 2016, the long snapper was just four months into his marriage with Olympic gold medal-winning gymnast Shawn Johnson and they were on the hunt for double dating buddies. So the newlyweds encouraged Underwood to film a video message asking out Johnson’s pal, fellow Olympian Aly Raisman

“Just wanted to congratulate you on all your success in the competitions and representing the USA over there,” he said in the video that Yahoo! Sports played for a bashful Raisman, fresh off a three medal showing at the Rio de Janiero games. “I know I’ve been following along. My roommate, my teammates, everybody here is super proud of you. You know, if you’re ever in San Jose and wanna go on a double date with me and Andrew and Shawn, let me know.” 

Frazer Harrison/Getty Images

The 25-year-old’s obvious interest—”He’s very cute, yeah I would go on a date with him,” she told the interviewer—and subsequent tweet telling Underwood “Looking forward to meeting you,” turned them into a couple most of America was rooting for. So people were thrilled when they showed up on the step-and-repeat at the Sports Illustrated Sportsperson of the Year Ceremony that December, confirming that, yes, they were a couple. 

“We happened to both be in Denver at the same time,” she told People of their first date, which took place not long after she and her teammates attended the MTV VMAs in August. “I was there for less than 12 hours, he was flying in for just a few days. it just ended up working perfectly.” 

And for a spell they had one of the most endearing romances in young Hollywood. She spent Christmas at his grandparents’ place in Illinois, gamely wearing matching festive PJs. He turned up as her date at the Golden Globes. Soon he was tweeting out public Valentine’s Day wishes and she was praising him for working around her peripatetic existence.

Courtesy of Sea Fire Grill

“He’s been just very supportive, coming with me and keeping me company because I’m in a different hotel all the time,” she told Us Weekly that January of navigating her Kellogg’s Tour of Champions. “My New Year’s resolution was to make more ‘me’ time, so I’ll go visit him more and I told him I have to learn how to cook for him, because he eats really healthy. So I’ve got to learn how to cook some good stuff.”

Together, the two athletes enjoyed bingeing This Is Us and, naturally, hitting the gym. “We have now boxed together in four different cities, so we hit somebody up and we find a gym and it always works out great,” he said. “It’s really different than what we’re used to, training-wise, so it’s really good for your body.”

Having him as a workout buddy was extra motivating, she added. “We like to give each other workout tips because I think it’s good for both of our sports. I work out more when I’m with him because he gets up and I feel bad lying in bed while he works out.”

Slaven Vlasic/Getty Images for Sports Illustrated

But then the fight fizzled out of the romance with little explanation, except that sometimes it’s hard to date an Olympic athlete who has a side gig as a crusader for survivors of sexual assault. “We’re taking a break right now,” he revealed during a June 2017 phone interview with the Peoria Journal Star to promote his Legacy Foundation’s third-annual football camp. “We’re still good friends and talk, but all that travel had been a nightmare.”

As for their relationship now, “It ended fine,” he swore. “We’re in a good place.”

Splitting from the woman he would later call “my first love,” was certainly tough, and harrowing enough that he labeled it his worst heartbreak during a January 2019 appearance on the LadyGang podcast. Still, he said, “While it was confusing and it was hard in the beginning, it also taught me a lot about myself: What I need, what I want, what I can do better in a relationship. It was a big step for me. It was really tough.” 

And yet something even messier was ahead just on the horizon. 

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Hey @coltonunderwood remember that time you wore a sleeveless sweatshirt at the beach and then we realized we were 0% compatible and solely meant to be supportive friends?… Well here’s my support. Now keep your damn shirt on and go find you a gal🌹#thiswasafterparadise #yeahitspossible #calmyourtits #thirsty #extra #allingoodfun

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The twist, of course, was that she was legitimately friends with newly named Bachelorette Kufrin and certainly close enough to be one of the alumni chosen to help the publicist separate the men from the boys during one memorable group date. The relaxing spa outing turned a wee bit tense when Booth and Underwood shared their romantic rendezvous, but everyone involved insisted they were over it. Booth swore their fling was in the past and Underwood assured Kufrin he was definitely there for the right reasons. 

Which he was, falling so hard for the bubbly Minnesota native that “I was ready to really take the next step,” he swore on the show. “I was ready to lose my virginity to Becca.” (And, presumably after that, select a Neil Lane diamond of her choosing and get down on one knee.) 

Kufrin, however, felt differently. While Booth’s last-minute confession that, actually, yeah, she was still crushing hard on Underwood and it had been hard to stomach that her friend was falling for him too doubtlessly complicated things, she said she intended to send him packing after hometowns either way. 


“I don’t know if we can completely say my future with Becca was ended 100 percent on Tia,” he told Higgins and Iaconetti. “I’m sure that that was a heavy portion of why my future with Becca was ended, so yeah, of course I was sad. I was disappointed, I was frustrated, I was pissed off. I had every emotion going through me at that time and I didn’t know how to process it. I mean, I think—you guys watched the breakup—I was speechless.”

Crushed, he accepted his consolation prize: an all-expenses paid trip to the Playa Escondida Resort where Booth would be waiting in Paradise

“I feel like we just have a big question mark right now because we haven’t talked since he left for filming and we saw each other on the group date,” Booth told E! News. “Going into it I would be nervous to talk to him if he was here, but it would also be a relief just to have everything out on the table.” 


Bachelor’s 2018 Love Connections

So whether the pair would combust or ride off into the Mexican sunset was up for debate. “They haven’t talked, there’s so much tension,” host Chris Harrison shared with E! News. “I feel like that’s going to melt down or it’s so hot they’re just going to make babies.” 

For a little while, anyway, both options seem equally likely. From the moment Underwood set foot on the beach, the whole cast, especially Booth, seemed certain that they would couple up and being their journey to Tanner TolbertJade Roper status. So when he didn’t make it immediately clear he intended to end the season on one knee, his rose-seeking counterparts turned on him. His all-American good guy veneer already cracking, he went into full meltdown when Kufrin made a surprise appearance on the beach. 

In an effort to provide him with the closure he so desperately needed, she encouraged him to get in touch with his emotions. “You know you’re a strong person. It’s okay to cry. It’s okay to feel things that aren’t always pretty and perfect,” she shared. “Don’t be ashamed to let that out.”  


So he did, his outpouring of emotions leading him to the realization that actually he wasn’t ready to wife Booth up. The on-camera breakup, though painful to watch, gave another ex a chance to offer up some sage words, with a clearly devastated Booth telling Underwood, “You need to just really focus on this time and really figure yourself out, so you can fully give yourself to someone.” 

Fast-forward a handful of months and he was declaring himself ready to give his all to many someones. As the Bachelor, he was the safe choice ABC felt the need to make after the somewhat rocky appearances that were Nick Viall and Luyendyk Jr. A former pro athlete who’s dedicated his life to helping children fight Cystic Fibrosis with a cute dog to boot? Perfect wholesome fare. “

His only challenge has been to prove he was ready, really ready to commit to a forever, something he’s sworn up and down to every interviewer that asked. 


A Look Back at Bachelor Nation’s Most Dramatic Year Ever

“I have a ton of life experience. I’ve had so many unique opportunities and just some great things that have happened in my life, but when I look around and I look back at it, I’m missing someone to share that with,” he told Us Weekly. “I like to say, I might be 26, but I’m in mid-30s as far as life experience goes.”

In retrospect his ending was equal part requisite drama and one of the happiest the franchise has received in a minute. “For some reason I’m extra grateful tonight that a girl like you ended up on a tv show with me and we fell in love,” he shared on Instagram following Peter Weber‘s finale finish. Agreed his future bride,  “I’m so grateful for our strange circumstances and how they led us to each other.”

(Originally published Jan. 21, 2019, at 3 a.m. PT)

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