The Biggest ‘Bachelor’ Bombshells in Colton Underwood’s New Book ‘The First Time’

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The Biggest 'Bachelor' Bombshells in Colton Underwood's New Book 'The First Time’

Colton Underwood is telling all. The former Bachelor gave fans insight into his time handing out roses in his new memoir. “Only 26 years old at the time, I was trying to figure myself out and constantly asked myself such questions and more,” Underwood wrote in in The First Time: Finding Myself and Looking for Love on Reality TV, which was released on Tuesday, March 31. “Who was I? What should I do with my life? Perhaps identity and the search for it was a lifelong quest.” Underwood first competed for Becca Kufrin’s heart on season 14 of The Bachelorette. After his elimination, the former football player had a stint on Bachelor in Paradise 5. He was subsequently named the new Bachelor. “Out of the thirty contestants that night, I think five or six were picked especially for me,” Underwood wrote about filming the first episode of season 23 of The Bachelor. “They were the likely matches, the maybe-she-might-be-the-future Mrs. Underwood. The rest were strong, colorful personalities, with a couple of question marks, a couple of possibilities, a couple of you-never-knows, and a few unpredictable wild cards.” After night one, Underwood named Hannah Godwin, Caelynn Miller-Keyes, Tayshia Adams, Hannah Brown and Annie Reardon as his standouts. That doesn’t mean the eventual winner and his current girlfriend, Cassie Randolph, didn’t leave an impression, however. “Cassie Randolph handed me a box and said that she had butterflies, meaning she was nervous, though she added that she also had actual butterflies,” he wrote. Then she spilled a box of fake butterflies in front of me. I put one in my pocket, while trying to hide the fact I was staring at her. I couldn’t help it. And yes, she was cute and sexy, but what I noticed were her high heels. They had a Velcro strap and seemed practical, cool. She wasn’t spending a month’s salary on those heels with the red bottoms. I liked that about her.” [jwplayer Plpj32AF-l3ahXupL] In the book, Underwood spilled secrets about how he really felt about his contestants, when he knew Randolph was The One and what really went down when he infamously jumped the fence to escape producers. The reality TV personality also opened up exclusively to Us Weekly about writing the memoir on the “Here for the Right Reasons” podcast. “I think the whole goal in the book was just to sort of take ownership back of my story,” Underwood tells Us. “I've been so appreciative of The Bachelor franchise for obviously introducing me to Cassie and everything that comes along with the business side of things, which is great. But I wanted to take ownership of my story that starts with the title.” For details on Underwood’s life before he joined Bachelor Nation, head over to Us Weekly’s second The First Time revelations gallery. Or scroll through for the biggest takeaways about his time on reality TV: [podcast_block]

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The Biggest 'Bachelor' Bombshells in Colton Underwood's New Book 'The First Time’

Colton Underwood is telling all. The former Bachelor gave fans insight into his time handing out roses in his new memoir. “Only 26 years old at the time, I was trying to figure myself out and constantly asked myself such questions and more,” Underwood wrote in in The First Time: Finding Myself and Looking for Love on Reality TV, which was released on Tuesday, March 31. “Who was I? What should I do with my life? Perhaps identity and the search for it was a lifelong quest.” Underwood first competed for Becca Kufrin’s heart on season 14 of The Bachelorette. After his elimination, the former football player had a stint on Bachelor in Paradise 5. He was subsequently named the new Bachelor. “Out of the thirty contestants that night, I think five or six were picked especially for me,” Underwood wrote about filming the first episode of season 23 of The Bachelor. “They were the likely matches, the maybe-she-might-be-the-future Mrs. Underwood. The rest were strong, colorful personalities, with a couple of question marks, a couple of possibilities, a couple of you-never-knows, and a few unpredictable wild cards.” After night one, Underwood named Hannah Godwin, Caelynn Miller-Keyes, Tayshia Adams, Hannah Brown and Annie Reardon as his standouts. That doesn’t mean the eventual winner and his current girlfriend, Cassie Randolph, didn’t leave an impression, however. “Cassie Randolph handed me a box and said that she had butterflies, meaning she was nervous, though she added that she also had actual butterflies,” he wrote. Then she spilled a box of fake butterflies in front of me. I put one in my pocket, while trying to hide the fact I was staring at her. I couldn’t help it. And yes, she was cute and sexy, but what I noticed were her high heels. They had a Velcro strap and seemed practical, cool. She wasn’t spending a month’s salary on those heels with the red bottoms. I liked that about her.” [jwplayer Plpj32AF-l3ahXupL] In the book, Underwood spilled secrets about how he really felt about his contestants, when he knew Randolph was The One and what really went down when he infamously jumped the fence to escape producers. The reality TV personality also opened up exclusively to Us Weekly about writing the memoir on the “Here for the Right Reasons” podcast. “I think the whole goal in the book was just to sort of take ownership back of my story,” Underwood tells Us. “I've been so appreciative of The Bachelor franchise for obviously introducing me to Cassie and everything that comes along with the business side of things, which is great. But I wanted to take ownership of my story that starts with the title.” For details on Underwood’s life before he joined Bachelor Nation, head over to Us Weekly’s second The First Time revelations gallery. Or scroll through for the biggest takeaways about his time on reality TV: [podcast_block]

Credit: Courtesy Tia Booth/Instagram

The Tia of It All

Underwood met Tia Booth over social media before he was official cast as a contestant on season 14 of The Bachelorette. As a result, he briefly spoke to Kufrin, who appeared on Arie Luyendyk Jr.’s season of The Bachelor with Booth, via FaceTime before the season started.

“It was intimidating. But I managed to calm down and even enjoy meeting some of the guys,” Underwood wrote about The Bachelorette night one. “I’d already won a small victory. Becca hadn’t recognized me. Or she played it cool and didn’t say anything if she did. I had no recollection other than that I made it through our first hello without incident.”

While he debated telling Kufrin about Booth, she took it well. His relief didn’t last long, however, with Booth showing up on a group spa date. “I was only four days into this thing and knew I was in over my head. How did I not know this before?” he wrote about the group date. “There were too many moving parts to keep track of. I was up against masters. What saved me was Becca herself. I knew the final decision as to who got a rose belonged to her, not the producers, and I got a good vibe from Becca. I sensed that she was playing the game, but also that she really liked me.”

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He Told Jason and Garrett About His Virginity First

Underwood went into The Bachelorette with a secret: He was a virgin. In the book, he revealed that he told fellow contestants Jason Tartick  and Garrett Yrigoyen first.

“A week or two before Las Vegas, I had confided in my mansion-mates, Jason and Garrett, the two guys with whom I was closest. I don’t know why I felt compelled to spill the tea on myself other than it was weighing heavily on my mind. I suppose I was testing the water,” Underwood wrote, noting that Jason and Garrett were “surprised,” “supportive” and “talkative.”

He explained: “Apparently they interpreted my ‘please don’t tell anyone’ as code for ‘tell everyone,’ and word traveled through the house like a rumor at a slumber party of twelve-year-old girls that someone had gone to first base.”

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Telling Becca About His Virginity

“Up till this moment, you could count the times I had talked about it on one hand: to my ex-girlfriend, Tia, the show’s producers, several of the guys on the show, and a room full of NFL linebackers,” he wrote. “As I told Becca, I wasn’t even sure my dad knew. ‘It’s something I’m proud of and something that everyone I see a future with should know,’ I said."

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Becca’s Relationships With Blake and Garrett

Underwood and Tartick thought Blake Horstmann was going to win after seeing him make out with Kufrin off camera. “We kept that bit of intel to ourselves as we headed to the Bahamas week seven for sun and warm-weather fun,” he wrote. “At this point, I didn’t care whether I was among Becca’s top choices. I was in the Caribbean, and I loved it there.”

Underwood knew Yrigoyen was a contender when he learned they chatted about Kufrin’s late father. “Hearing this from Garrett let me know that he was way ahead of me with Becca,” he explained. “Their bond was in a deeper place. I still had hometowns ahead of me, but I resigned myself to this new reality. I was toast.”

Credit: ABC/Paul Hebert

Split From Becca

Underwoood wrote that he thought Tartick would come in 4th, he would come in 3rd, Yrigoyen would come in 2nd and Horstmann would win.

“It turned out I was mostly right. Garrett, Blake, Jason, and I were the four guys who made it to the hometowns. These were my best friends from the group, and I was happy for all of us,” he wrote. “Soon it was painfully apparent that Becca’s thoughts differed from mine. I didn’t get a rose. I was surprised and hurt. Not crushed. Not heartbroken. Not pretending to be okay when I wasn’t. Not stopped in my tracks and wondering where I went wrong or what mistakes I might have made. I was just hurt in the sense that I had been honest about myself and opened my heart and believed the emotions I felt were reciprocated, but in the end it wasn’t enough, and it wasn’t me. It was that kind of hurt.”

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He Knew Being on 'Paradise' Could Lead to 'The Bachelor'

“No one made any promises, but I got the feeling that if Paradise went well I might have a good shot at becoming the Bachelor,” he wrote. “I had to ask myself some questions: Did I want to be the Bachelor? And if so, how badly? Badly enough to go to Paradise, as Tia had foreshadowed all those months ago? Badly enough to engage with Tia again? It wasn’t as if we had a real relationship. We didn’t leave a romance broken or unresolved. We’d spent a weekend together and developed a friendship built on text messages.”

Bachelor fans, however, were rooting for Underwood and Booth. “She possessed all the qualities that made someone attractive. There was the obvious, and there was the part of Tia that shined even brighter when you got to know her,” he wrote. “Why then didn’t I feel that spark? That special chemistry that drew people to each other? I just didn’t. And for that reason I didn’t see us together. Then again, I felt like I owed it to Tia to see if she was right and if maybe I missed something as a result of being so focused on Becca.”

Credit: ABC/Paul Hebert

Ending Things With Tia

While the twosome tried to make their relationship work in Paradise, Underwood said he was “a mess” while trying to film the season.”I didn’t want to lead Tia on or lie to her. I also didn’t want to be anyone other than who I really was—honest, imperfect, and not in love with Tia,” he wrote.

He added that the twosome are on good terms now. “I felt terrible about breaking up with her, but I also knew it was the right thing to do, and she agreed,” Underwood wrote. “We were better off as friends, and we’ve remained friends. To this day, she is one of my most trusted confidantes.”

Credit: Courtesy Cassie Randolph/Instagram

Cassie Almost Did 'The Bachelor' Before

“Twice they invited her on the show, but Cass turned them down both times,” Underwood revealed. “The season with Nick Viall didn’t work with her schedule, and she thought the next Bachelor, Arie Luyendyk, was a little too old for her. But the third time was the charm.”

Credit: Courtesy Kirpa Sudick/Instagram

Behind-the-Scenes Secrets

“I wanted to send Kirpa Sudick home,” Underwood wrote about night one. “She was very attractive, but I wanted more connection with people than just appearances. Her hello didn’t work, and our short sit-down fell flat. My producer liked Kirpa and advised me not to judge her harshly.”

Underwood also hinted that producers picked who got to go on his one-on-one dates each week. They were, however, sympathetic at times. “They weren’t on TV, but boners are a real, regular, and unavoidable part of the show,” he confessed. “The producers are sensitive to guys who find themselves in a hard situation. I didn’t know this until I was in the ocean with Cassie in Thailand and production said they needed me for an interview. I wasn’t ready to get out of the water. … Poor Cass waited patiently while I splashed, yawned, swam, and waited for low tide.”

Credit: Craig Sjodin/ABC (2)

Caelynn vs. Hannah B.

Miller-Keyes and Brown famously did not get along while filming season 23 after they both competed in the pageant world together. “From what they told me off camera, their problem had to do with a tasteless joke about a serious matter related to one of their family members,” Underwood revealed. “I won’t say anything more. The tension of being on the show together opened this old wound and cast a dark cloud over the entire week.”

Credit: Courtesy of Hannah Brown/Instagram

Hannah B. Showed Up on Hometowns

Underwood revealed that Brown, who is also from Alabama, showed up on his date with Godwin, but the scene didn’t air. “She was still stewing about not getting a rose and wanted more clarity from me,” he wrote. “In reality, it seemed she wanted to lash out and vent. She went off on the remaining four girls and told me they didn’t have the qualities that made her so amazing. It was the beast in her, roaring and raging.”

Credit: ABC/Josh Vertucci

He Kept Tayisha Longer Than He Wanted

Adams lost credit with Underwood when he claimed that she and Miller-Keyes were plotting to be the Bachelorette. “I had trouble getting past my anger at the girls who’d dragged Cassie’s name into this drama,” he wrote.

He also noted that he kept Adams over Miller-Keyes because of Randolph’s close relationship with the former pageant queen. “I would’ve cut Tayshia, but I wanted to separate Cassie and Caelynn,” he wrote about the rose ceremony after hometowns. “I knew their friendship had grown and thought it might be interfering with my relationship with Cass. If Caelynn went home, it might let Cassie see that I was more serious about her.”

In the fantasy suites with Adams, Underwood wrote that she realized “nothing was going to happen” by “two or three in the morning” and Adams went to sleep. “I laid down next to her in my sweatpants and long sleeved shirt,” he explained. “I didn’t sleep all night.”

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Hannah G. Praise

Underwood had nice things to say about Godwin, his first impression rose recipient, throughout the book. “Despite my feelings for Cassie, I knew spending time with Hannah G. was important,” he wrote. “It was going to answer the tiny questions I had about the decision I would ultimately make. The time I had already spent with Hannah G. was enough to make me a huge fan and give me a sense that we could be very comfortable together. But it wasn’t enough time to know whether there was anything more than being comfortable, which was the special ingredient I wanted in a relationship. I didn’t want to wake up in the morning or go to sleep at night feeling comfortable. I wanted WOW.”

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Cassie Calls Him Out

Underwood makes it clear that he fell for Randolph while filming the show, but she wasn’t afraid to call him out. During a one-on-one date, she asked him off camera (they were in the ocean), “How do you not know by now?”

“I knew what she meant, but I wasn’t prepared for the directness and honesty of her question. Basically, she wanted me to flip to the end of the book and tell her how the story ended. I couldn’t. I didn’t know myself,” he wrote. “The one thing I knew about myself with absolute certainty was that I was sometimes confused.”

Credit: ABC/Rick Rowell

Betrayed by Producers

Underwood wasn’t happy when producers invited Randolph’s dad to Thailand during the final weeks.

“It was all clear and perfect and everything a parent should do. I’m sure that’s why my old pal, supervising producer Ruby Taylor, had called Matt in the first place,” he wrote. “She’d contacted him several days earlier and told him that Cassie was really struggling with her feelings and could use him as a sounding board. … It made me feel like production was working against me and trying to help Cassie break up with me.”

Underwood referred to Randolph as the “Queen of I Don’t Know” while filming the season. “She hit circuit overload, to the point where the easiest thing for her to do was also the hardest thing: walk away,” he wrote about her decision to leave the show.

Credit: ABC

The Infamous Fence Jump

After Randolph quit, Underwood infamously ran away from host Chris Harrison.

“I just did it. I expected to get caught the moment my feet touched the ground on the other side. When that didn’t happen, my adrenaline kicked in and I started to run through the Portugal wilderness,” he wrote about jumping the fence. “I was surprised I didn’t get shot or attacked by some animal. I remember hearing a growl while I was hiding in someone’s backyard and bracing myself to get jumped by a large dog.”

When Harrison caught up to him, Underwood told him to call Tartick or Horstmann to film a new season. “I wanted them to know how angry I really was. Once I felt confident they got the message, I needed a graceful way out of this situation,” he wrote. “It was 2:30 a.m., and I’d been out there for more than an hour when the show’s top producers and I huddled and had the most impromptu production meeting in the show’s history.”

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Back Together With Cassie

While viewers saw Underwoood invite Randolph to Spain and watched the two ultimately get back together after he sent Godwin and Adams home, he revealed in the book that Randolph’s off camera walk with her dad played a big part in her decision.

“Ironically, I later learned that Matt asked, ‘What if he breaks up with the other two and he comes back for you?’” Underwood wrote. “Cass said, ‘That would be cool, huh?’”