Colton Underwood Details Every Step of His Split With Cassie Randolph For the First Time

Eight months after Bachelor Colton Underwood's romance with final rose recipient Cassie Randolph wilted, he's sharing exactly what happened to make the situation so thorny.

By Sarah Grossbart Jan 26, 2021 8:00 AMTags

Sometimes the bloom comes off the rose. And sometimes it wilts, gets torn apart petal by petal and then thrown in an incinerator for good measure. 

Such was the case when Bachelor Colton Underwood split with his final rose recipient Cassie Randolph last May. Though their initial separation seemed friendly enough, the couple of 18 months putting out statements about how they were "just meant to be friends," the situation was much thornier behind the scenes and their journey eventually ended in a restraining order as Randolph accused her ex of "stalking" and "harassing" her. (Months later she dismissed the order, with Underwood telling E! News, "The two of us were able to reach a private agreement to address any of Cassie's concerns.")

And though Colton doesn't delve into those particulars in a newly penned final chapter to his 2020 book The First Time, released on his 29th birthday Jan. 26, the experience doesn't sound all that great. 

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"Falling in love is like open-heart surgery," he wrote of the experience. "Breaking up is like seeing your heart in someone else's hands and realizing the anesthesia has worn off. Geez, it hurt. The pain was excruciating."

And it didn't help that he was recovering from actual excruciating physical pain. Because it was right around the time the former NFL tight end was diagnosed with COVID-19 last March that their problems really began to crystalize.

The deal-breakers had always been there, he shared in his book. "Cass felt there was pressure on her to commit one way or the other because of the way our relationship unfolded so publicly on television," he noted of the constant questions about when she might be ready for an engagement. "I tried to give her space. She didn't feel like I saw all the different sides of her, especially the small-town girl who liked the slow pace and quiet of her beachside hometown. Sometimes she would say outright, 'I feel like you don't understand me.'"  

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But that issue was ever-so-slightly pushed to the backburner as Cassie and her family helped Colton recover from the virus that left him shivering, drenched in sweat and terrified he might actually die. "I struggled to breathe. Nothing is scarier than not being able to fill your lungs with fresh air," he detailed of the weeklong experience. "They worked at about 20 percent capacity. Everything hurt, from the bottom of my toes to the top of my head." 

But as his fever broke and he began hanging out around her family ("I regret that I was sometimes more stupid than smart when it came to always wearing a mask," he admitted), California's stay-at-home orders placed another burden on their struggling romance. 

"It was when Cass and I finally tried to grab back a bit of normalcy that I realized the virus was only part of a much larger problem," Colton wrote. "After more than a month of being cooped up in her family's home, both of us were feeling overwhelmed and smothered and eager to return to our respective apartments where we could enjoy our own space. Before we left, though, she took me aside and told me she was struggling with everything in our relationship and didn't know what to do. My head spun like one of those characters in a cartoon. What? She was struggling with everything?"

Once the shock wore off, he realized that the "misfires and miscues" between them were actually more like "one of those proverbial deaths by a thousand paper cuts" to Cassie. But in the moment, he wasn't ready to hear it. 

"I put my finger to my lips for silence. She stopped mid-sentence," he shared. "Both of us had always agreed to avoid finishing hard conversations like this one. We didn't want to come to the conclusion that we weren't good for each other. We were scared of confronting that truth. So we didn't."

But for all of his attempts to go back to the connection they had as they celebrated their first anniversary in St. Lucia, it became clear their relationship "was essentially over save for the three magic words, 'We're breaking up.'" 


Though he returned to her family home to celebrate her April birthday, two days later he drove to stay with family in Colorado, keeping in touch with his now-ex-girlfriend intermittently. 

"Our conversations were delicate check-ins," he wrote. "We were friendly but real. She wanted to talk about how to move forward and remain friends, while I held on to hope that we could get back together after some time passed. Finally, Cass called and said she wanted us to make a public statement about our breakup. Our Instagram accounts were filled with speculation about our status, and she wanted to put it to rest."

Making it Insta-official felt "too final," he admitted. "I didn't want to put out a statement. Period." But ultimately it wasn't his call. 

"You don't need to be a therapist to understand why I was so resistant," he continued. "I didn't want to break up. I didn't want to accept that Cass wanted to break up with me. I didn't want it to be over. I didn't want any of this to be real."

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They cried over FaceTime as they posted their statements and months later met up for one final date. "Afterward, she came back to my place, where we had a few drinks, hung out, and we were Colton and Cass again the rest of that night," he detailed. "Then, when we woke up the next morning, I could tell everything was different. I had the urge to say I love you before she walked out the door, and I sensed she did, too. No door shut that softly has ever made a louder sound."

His recovery has gone far better than expected, he shared, as he filled his days recording his Internet talk show Coffee with Colton and working toward deals on TV and clothing projects. 

"I think I'm headed in the right direction and letting my faith shine the biggest light on where I need to go," he said. And he knows the journey he started back at the Bachelor mansion all those months ago is far from over. "I also love that this last chapter is only the next chapter," he explained. 

So let's all "cheers" to him continuing to document each one. Because the first chunk, laid out in his New York Times bestseller, is a must-read and, much like falling in love, should be experienced over and over. We've broken out the best bits for you to consume below—hot tub and champagne glass optional, but heavily encouraged. 

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."