The former football player tells all in his new memoir, 'The First Time.'
Bachelor Nation went through a lot with Colton Underwood over the three seasons he spent with the franchise last year -- but the former football player has even more to share.
The 28-year-old's virginity propelled him to fame on Becca Kufrin's 2018 season of The Bachelorette. His past with Tia Booth landed him a spot on that summer's Bachelor in Paradise, and we strategized his way into nabbing the coveted spot as Bachelor.
It was on The Bachelor that he found what he was looking for out of the franchise -- love -- but not without drama. In his new book, The First Time: Finding Myself and Looking for Love on Reality TV, Underwood opens up about finding his happy ending with Cassie Randolph and the many famous relationships that got him there.
From his sexuality, virginity and quitting The Bachelor, here are the biggest revelations from Underwood's memoir.
He Turned to Google to Help With His Sexuality Questions
Underwood had his first kiss as a high school freshman, but didn't feel the desire to go to the next level in any of his relationships. After suddenly dumping a girlfriend who wanted to go further than he was willing, rumors circulated that Underwood was gay. Those rumors reached his mother, who assured him they'd still love him if he was gay. His father, meanwhile, discovered Underwood was questioning his sexuality through his search history.
"He'd called up the history of recent Google searches, which included gay porn sites and a variety of questions: Am I gay? How do you know if you’re gay? Why don’t I like having sex with my girlfriend?" Underwood recalled.
He kept his sexuality mostly to himself, until he reached the NFL and was questioned about his "number" by fellow players. It was there that he finally revealed it was "zero" -- to some supportive comments, and others, like, "Underwood, man, I know someone who can help fix that."
Aly Raisman Was His First Love, But Ended Things Suddenly
Underwood was set up with Raisman by football friend Andrew East. The pair just clicked, and after their third date together, during which they spent the night together, she asked him if he was a virgin. He told her the truth -- he was.
"I do believe it relieved her in some way of concerns she might have had about my expectations. The slow lane was fine with both of us. We could take our time without any kind of pressure, certainly not from me," he wrote.
Underwood fell hard and fast, telling Raisman he loved her just months after they started dating. It was an accident, after he thought he heard the gymnast drop the L-bomb. She had actually said, "I love Ne-Yo."
While Underwood was honest with Raisman about his virginity and his feelings toward her, he kept other secrets -- like the fact he was broke. The shoulder injury that ended his NFL career also left him broke. "My shoulder surgery, at a cost of $40,000 to me, took most of my savings. The rest went for plane tickets and hotels to see Aly. I even sold my car," he explained. "I loved her. I could tell her anything and everything -- except that I had no money."
Later, it became clear that Raisman was also keeping things to herself, but for a different reason. The Olympian was going through her own healing after the abuse she endured from disgraced USA Gymnastics doctor Larry Nassar. Underwood didn't know all the details of what Raisman had been through, but he had strong feelings about what had happened to her. "I wanted to find Nassar and rip his head off," he said.
Underwood had told Raisman he loved her months before she reciprocated those feelings, but just two weeks after she told him she felt the same way, she FaceTimed him and ended their relationship.
"I pulled over to the side of the road, stunned and unable to comprehend this was happening. Aly said she felt overwhelmed, confused, and in need of a break. Afterward, I sat in my car and cried," he wrote, recalling feeling "numb for days."
Underwood tried to get clarity from Raisman, but she didn't respond to his calls and texts. So, finally he reached out to her best friend, Simone Biles. "She was also surprised. Left without any answers or information, I didn’t know what to do or where to turn. I went for long runs and replayed conversations in my head, wondering if I’d said or done anything wrong," he remembered.
He Became "Obsessed" With Getting on The Bachelorette
Underwood was cast on The Bachelorette after walking by a casting call for Arie Luyendyk Jr.'s season of The Bachelor. As casting process continued, Underwood became "officially obsessed with getting on The Bachelorette." "I was thinking about it nonstop, like I had OCD. I wasn’t like that a few days earlier; my attitude was more let me see what’s up. After going to their office and talking to all those people, though, I emerged a convert. And hopefully a contender. I wanted them to pick me. Memories of my football career. I wanted to make the team. But my reasons were in line with the show’s purpose: I wanted to fall in love and get engaged," he said.
Underwood was held onto the hope he got from a few of the franchise's successful couples, like Trista and Ryan Sutter and JoJo Fletcher and Jordan Rodgers. He then emerged himself in everything Bachelor Nation. He watched past seasons and read recaps, dived into comments and familiarized himself with the fanbase.
"I found the same level of fanaticism, insider’s knowledge, and passion as the NFL. Like football fans, those in Bachelor Nation were deeply involved in and opinionated about everything that happened on- and off-screen," he said. "They were already posting thoughts about the newly posted roster of girls participating on the new season of The Bachelor."
He Wanted a "Head Start" With Booth
After discovering Luynedyk's list of contestants and who fans thought might make it far, Underwood decided to follow Kufrin, Lauren Burnham and Booth on Instagram. "If Tia was going to be the Bachelorette, I wanted a head start on all the other guys," he said.
Neither Burnham nor Kufrin responded to him on Instagram -- but Booth did, and they started talking.
"I think Tia had similar thoughts. Both of us were playing a game, trying to gure out our next moves and have some fun in the process. What was the harm in that?" he asked.
After a settlement from his lawsuit against the Raiders, Underwood met with casting directors again in Los Angeles, and decided to make a weekend out of it -- inviting Booth to join him on a romantic weekend. They enjoyed their time together, and he told her about his virginity. Underwood remembered Booth encouraging him to still go on The Bachelorette, which was looking at that point to be Becca Kufrin. Booth allegedly told him, if things don't work out, maybe "I'll see your a** in Paradise."
He Initially Didn't Tell The Bachelorette About His Virginity
Underwood's virginity got him cast as the Bachelor, but it wasn't the reason he was cast on The Bachelorette. During a meeting with production before the show, Underwood was asked what his "number" was -- but he played coy, replying that he could count it on one hand.
He didn't reveal he was a virgin until after Kufrin's season had begun. He had confided in his producer about his other secret -- knowing Booth -- but didn't didn't discuss his virginity until week five, before his one-on-one date with Kufrin.
He Knew Kufrin Wouldn't Give Him Her Final Rose
Underwood and Kufrin connected as her season continued, but he knew they weren't meant to be together.
"I knew Becca wasn’t going to pick me in the end, so I was able to say goodbye to everyone in Nassau and mean it when I said, 'Good luck,'" Underwood said.
The former football player did, however, think he was a "shoo-in" for fantasy suites, given his big virginity reveal. He had himself pegged to make Kufrin's top three. "Who could possibly be more awkward, nervous, and funny in that situation than me?" he said, explaining that he knew he was making for good TV when he approached Chris Harrison with fantasy suite questions ahead of the rose ceremony.
"But soon it was painfully apparent that Becca’s thoughts differed from mine. I didn’t get a rose," he revealed. "I was surprised and hurt."
He Went on Bachelor in Paradise Hoping to Be The Bachelor
Fans will remember how Kufrin sent Underwood home after Booth had come forward, telling her she still had feelings for him. And that made for a great story, if Booth and Underwood both went to Paradise.
Underwood was propositioned to join the spinoff after returning home from filming The Bachelorette, and was unsure. "I wanted to be the Bachelor," he remembered.
"From the first time I heard the idea mentioned, I thought about myself in that role. I didn’t know how much I wanted it, though, until I faced the possibility of not being the Bachelor," he wrote. "I wasn’t done with the excitement or the people involved in creating it. I also wasn’t done with the experience itself. I had this sixth sense–like feeling that it was going to work for me. If I was the Bachelor, it would be me and thirty beautiful, bright women eager to win my affection. I liked those odds."
Underwood knew Paradise upped his chances of making an impact and getting the fanbase needed to secure the gig. "I called the producers. I was in," he said.
His Tell All Performance Was Part of His Bachelor Audition
Things didn't work out for Underwood in Paradise, and while he went in trying to make enough of an impact to become Bachelor, he really did try to give things another shot with Booth. When it didn't work out, he was back on his Bachelor mission. "By midsummer, my communication with the show about The Bachelor grew more frequent and detailed. I learned it was between me, Jason [Tartick], and Blake [Horstmann]. Producers were monitoring our popularity as the season progressed," he said.
Shooting the Men Tell All was just another part of his way to audition for the gig. "I didn’t know what formula producers measured popularity by, but I wanted to use the platform to grow mine. I had to find a way within the hour-long show to create some positive buzz," he shared.
He Requested an On-Site Therapist for The Bachelor
Underwood eventually got the gig, and part of his list of requirements was that a therapist was on-site during production.
"I’d started seeing a therapist when I played for the Oakland Raiders, and I was still an advocate of paying attention to mental health issues, including my own," he explained. "I wasn’t 100 percent every day. Who is?"
Randolph Had Turned Down The Bachelor Twice
As Underwood revealed, Randolph had met with casting directors years before she appeared on The Bachelor.
"Twice they invited her on the show, but Cass turned them down both times -- 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," he said.
The Hannah Brown and Caelynn Miller-Keyes Drama Wasn't What It Seemed
Onscreen, Brown and Miller-Keyes' feud appeared to be a result of beauty queen drama gone wrong. Offscreen, they explained to Underwood there was a different motivation for their beef.
"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 said. "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."
He Wanted to Quit the Show Before Fantasy Suites
Underwood had been falling for Randolph for weeks, and after a rough hometown date with her family in Huntington Beach, California, he couldn't stop thinking about her.
Once he got to Portugal, Underwood sat down with producers, letting them know Randolph was the only woman he was thinking about. "I don’t want to do this anymore," he told them. "I can't fake it."
He Really Planned to Leave the Show After Hopping the Fence
After storming off from his breakup with Randolph, Underwood knew his way out was "up and over" that fence. "I never considered the height of the gate or whether I could pull myself up and hurdle to the other side. I just did it," he said. "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."
Underwood didn't know where he was or where he was going to go. He just took off, running for what seemed like two miles. He planned to go to the US embassy, use the documents in his wallet to get a temporary passport, and fly home. "I’d pay for it myself. I never considered there might not be a US embassy in the small town where I was headed (there wasn’t). Or a bank. Or a taxi. Or anything else that might get me from Portugal to Denver before the show’s producers caught me," he wrote. "I just wanted to go home and be done with The Bachelor."
The former football pro did his best to avoid the producers trying to track him down. He darted into the woods when he saw cars driving by and hid in people's backyards. Then, Harrison finally caught up with him.
"Y’all can call Jason or Blake and film a new season," he barked out.
He and Randolph Broke Up After the Show -- But Got Back Together
With no pressure of an engagement in the finale, things worked out for Underwood and Randolph -- until it didn't. "In August, Cass and I broke up," he wrote. "Nothing big happened between us as much as little things built up until they became big. It boiled down to me wanting to get engaged, wanting to set a timeline, and simply putting too much pressure on her when, in reality, none was needed. I wanted more. She wanted me to relax and smell the roses. In other words, don’t push. Don’t pressure. I interpreted that to mean she didn’t care about our relationship."
The pair got into an emotional argument, with Randolph leaving Underwood's house in tears. "Fourteen hours later, she knocked on my door and we talked the rest of the day and into the night. In the process, other issues came out. She pledged to help me have a better relationship with her family, and I promised to chill. It was one of those things that new couples have to go through to discover and develop the resiliency needed in relationships."
Underwood and Randolph worked through their issues, and continue to fight for their relationship today. "We were continuing to learn communication, understanding, compromise, and a willingness to forgive. Also just how much we really, truly wanted to be together," he said.
The First Time: Finding Myself and Looking for Love on Reality TV is now available where books are sold.