Colton Underwood Talks Sexuality, Bachelor Stardom and His Many Exes in Juicy Book

Colton Underwood tells all in new autobiography "The First Time" which details his rise to stardom and how he ended up with Cassie Randolph

By Cydney Contreras Mar 31, 2020 11:00 AMTags
Watch: Colton Underwood Reveals Lifelong Struggle With Sexuality

Colton Underwood is serving up some piping hot tea in his new book The First Time.

There's so much more to this Bachelor than meets the eye, and now, fans of the former footballer are getting to know what he really experienced during his time on the show, and most importantly, what happened behind-the-scenes.

But, since this is a book on his path stardom, Colton starts at the beginning of his life. He details his humble start as a footballer, his relationship with Aly Raisman and how all this impacted his decision to be a virgin. Some stories are new, while others are not, like how Simone Biles guided him through his breakup. 

Then, he delves into how he became one of the famous members of Bachelor Nation, revealing how he studied past episodes and befriended one of Arie Luyendyk Jr.'s top three women. 

Colton Underwood & Cassie Randolph's Cutest Moments

All of which led him to the most pivotal moment of his life: Becoming The Bachelor

To find out more about the shocking bombshells he shares, check out the gallery below!

Questioning His Sexuality

Despite dating multiple women in his lifetime, the Bachelor star still questions his sexuality. He said it began in high school when he dated a girl who wanted to go further than he was willing. This forced him to dump her without explanation, causing a flurry of rumors that he was gay. Speculation grew so rampant it eventually got to his mother who told him one day, "You know, Colt, we'd still love you and support you if you were gay." Brushing off the conjecture, he stuck to his guns and maintained his virginity even as he joined the NFL. When he did tell his teammates about his track record, none questioned his motivations, although one quipped, "Underwood, man, I know someone who can help fix that."

His First Love

On many occasions, friends and footballers tried to set Colton up with girls, but the only one to be successful was Oakland Raiders long snapper Andrew East, who matched him with Aly Raisman. He first asked her out in a video congratulating her on her gold medal, which landed him an "easy steak dinner" date. Eventually, they met up and he thinks Aly finding out that he was a virgin helped their relationship progress. "We could take our time without any kind of pressure, certainly not from me," he explained in the book. They fell in love, although Colton was the first one to say it—inadvertently. He shared that one day she whispered, 'I love Ne-Yo," while they listened to music and he thought she said, 'I love you," so he said it back. Awk!

Love and Loss

Colton revealed that he and Aly went public with their relationship during a particularly tough time. He was "broke" and she was slowly starting to open up, both publicly and in private, about the abuse she endured under USA Gymnastics team doctor Larry Nassar. "I wanted to find Nassar and rip his head off," he admitted of learning about his atrocities. Other than that, the star tried to be "kind, sensitive, patient and available" as Aly navigated the difficult time. In doing so, he felt "she was finally able to tell me that she loved me." Two weeks later, though, she dumped him. Stunned, he asked Simone Biles if she knew why Aly broke up with him, but Simone was just as "surprised." Eventually, he realized she just needed space. 

Pure Chance or Strategy?

While on a stroll at the local mall, Colton stumbled across producers holding an open casting call for women to appear on Arie Luyendyk Jr.'s season of The Bachelor. Though he wasn't quite the single lady they were seeking, producers asked him to apply for the next season of The Bachelorette that would see Arie's ex Becca Kufrin doling out roses. Looking to find "a way out of this rut" he was in, he began the process and became "obsessed" with getting on the show. As such, he approached the casting process like he would football, leading him to immerse himself in "all things Bachelorette." In doing so, he befriended potential Bachelorette lead Tia Booth and they struck up a close friendship, something he assumed was forbidden. 

Mission Accomplished

His hard work and research paid off when he found out he was cast for the new season. At the same time he pocketed a settlement from a lawsuit with the Raiders that afforded him the opportunity to plan a romantic L.A. getaway with Tia. He said his father "warned" him about the problems this could cause, but Colton hoped Tia would be cast as the Bachelorette and he'd get a "little head start" in the process. Unfortunately, it was Becca, not Tia, who was chosen, but Tia encouraged him to go on the show anyway telling him that if things don't work out, maybe "I'll see your ass in Paradise."


The day finally came when Becca's season aired and Colton was "excited and scared" because he "opened up about personal issues in ways I'd never shared with my family or close friends." Over the years, he explained, he'd fabricated stories about hookups with girls, because it "was easier to lie than to tell the truth." But again, to his surprise, people didn't judge him the way he expected. Instead, friends, family, strangers and even Becca told him they were "proud" of his honesty. 

Becoming The Bachelor

Colton once again began to strategize, this time with the goal of becoming the next Bachelor. He used his appearance on the Men Tell All special as his opportunity to create "positive buzz" and thought of one-liners to make him stand out during the show. He took aim specifically at Jean Blanc because he figured, "You can't lose defending a beautiful woman's honor." It worked and he met with multiple producers, including Mike Fleiss. The show creator asked him if he was willing to lose his virginity on the show and Colton said yes, but only if it were the "right person." Beneath all his careful planning, he shared, he genuinely wanted to become the Bachelor to "fall in love and get married."

Meeting the Women

As filming kicked off, Colton began to get a feel for all the women. On first impression, he liked everyone, but was "scared" of Demi Burnett because of her sexual nature. He was most intrigued by Cassie Randolph but he couldn't go "off-script" and tell her how strong his feelings were. And while Caelynn Miller-Keyes and Hannah Brown were among his front-runners, their feud "didn't sit well" with him. 

Finding The One

He may have been a virgin but Colton still had "real physiological responses" to his and the girls' interactions. He became aroused multiple times around Hannah Godwin and some others, but he soon realized he was legitimately "falling in love" with Cassie. His requests for time with her fell on deaf ears, though, and the producers encouraged him to stay open since "you never know what's going to happen." He started to feel fed up with all the scheming, which is part of the reason why he sent Demi home when she showed up at his hotel to tell him she was falling for him. "I think she intended to come over to have some fun," he wrote, "and then go back to hang with the girls and stir the pot." 

What Happened in the Fantasy Suite

A whole lot of drama, two breakups and one fence jump later, Colton and Cassie were finally ready to go on their Fantasy Suite date. Even though they had removed their mic packs, Cassie and Colton were convinced the cameras were secretly rolling and searched every nook and cranny only to discover a "couple hundred" condoms. What happened next, however...well...he's not telling all, writing that's "none of your business."

Happy Ending?

By the end of the book's initial release, Colton and Cassie were happily together and while they weren't engaged, he had every intention of becoming her groom. "Now, a year later, she still gives me butterflies every time I see her," he wrote. "I do my best to make her feel the same way about me. Will we always be together? I hope so. We want our happily ever after. We are working at it. But I can't see into the future. I focus instead on loving Cassie today and tomorrow, and knowing that love comes back to me tenfold. If that continues, we will have our forever."