Colton Underwood Reveals How Split From Cassie Randolph Happened in Book’s New Chapter: ‘Was There a Timer on Our Relationship?’

More to the story. Colton Underwood is opening up about what really happened at the end of his relationship with Cassie Randolph for the first time. In July 2020, the former Bachelor, 28, wrote a new chapter for The First Time: Finding Myself and Looking for Love on Reality TV, the memoir he released in March.

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The new chapter — which Underwood says Randolph, 25, read and signed off on before it was printed — details his experience with the coronavirus, quarantining at her family’s home and ultimately what led to their split. The former NFL player and the speech therapist, who met on season 23 of The Bachelor, announced their split in May 2020 shortly after he recovered from COVID-19.

In an exclusive excerpt obtained by Us Weekly, the Indiana native shares that after his COVID battle, his then-girlfriend shocked him by telling her she was having a tough time with their relationship. While he encouraged her that they should try getting back to normal together, it didn’t work.

Colton Underwood Reveals How Cassie Split Happened Book New Chapter
Colton Underwood and Cassie Randolph. Janet Mayer/Startraksphoto.com; Shutterstock

Read the full exclusive excerpt below. The paperback edition of The First Time: Finding Myself and Looking for Love on Reality TV is available on Amazon Tuesday, January 26.

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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?

In a calmer moment, I agreed we’d worked through some misfires and miscues lately, little things where we didn’t see exactly eye to eye, but I didn’t realize how much those little things had been impacting her. It was one of those proverbial deaths by a thousand paper cuts. Her eyes were full of tears as she tried to explain, struggling to find the right words and reasons that made sense. None did—at least not to me.

Finally, I put my finger to my lips for silence. She stopped mid-sentence and lowered her eyes. 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.

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“Hey, let’s just go back, just you and me,” I said, trying to stay calm. “We haven’t had any alone time. I’ve been sleeping on the third story like a squatter. We haven’t been intimate. We haven’t even held hands. Let’s try to make some time for us.”

For the next several days, we hung out and returned to normal the best we could considering the circumstances. When we drove back down to Huntington Beach a few days later, I brought up a project we were planning together and got an unexpected response. She said she didn’t know if we should jump into another project together when there was so much uncertainty in our relationship. Uncertainty? That hit me hard. Was there a timer on our relationship? What was going on? Were we together or not together? “Are we breaking up?” I asked.

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