‘The Bachelor’: Did Colton Underwood Hint at His Breakup With Cassie Randolph Back in March?

On May 29, former bachelor Colton Underwood and his season winner Cassie Randolph announced that they’d broken up. In Underwood’s Instagram post he wrote that “sometimes people are just meant to be friends – and that’s okay.” In her caption, Randolph wrote that she wants Underwood to continue to be involved in her life.

Cassie Randolph and Colton Underwood attend the 2019 MTV Movie And TV Awards.
Cassie Randolph and Colton Underwood | Emma McIntyre/Getty Images for MTV

Colton Underwood didn’t have any ‘certainty right now’ about his relationship with Cassie Randolph in March

The former football player was interviewed by Entertainment Tonight back in March, and he seemed to be filled with uncertainty about his relationship with Randolph.

“There is no certainty right now. I mean we’re not engaged, we’re not married. I love her to bits and pieces and I think that for us, we just need to keep communicating and having those open conversations with one another,” he said. “I mean, we’re just taking it day by day right now.”

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On March 20, Underwood announced that he had coronavirus (COVID-19). Randolph and her family helped to nurse him back to health.

“While [Colton Underwood] told ET he was grateful to have [Cassie Randolph’s] support amid his coronavirus recovery, it hadn’t made him want to propose,” reported the publication.

“It’s still a day-by-day thing at this point,” he reiterated. “There is not certainty right now in this world.” 

Colton Underwood and Cassie Randolph: What went wrong?

The reality TV star reflected on what caused problems between him and Randolph in the past.

“I put a lot of pressure on our relationship when I was always defending it or I was overcompensating and trying too hard. I was almost pushing her away by trying to bring her closer,” he said. “I was saying, ‘No, we’ll be fine. We’ll be engaged by this date. We’ll do this, we’ll do this, we’ll do this.’ And it was sort of overwhelming her all over again.”

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Underwood admitted that he and Randolph weren’t always on the same page about how to handle their relationship in the public eye.

“[I said things] like, ‘We need to talk about this. You can’t just, like, go out in the media and say this,’ or ‘You can’t just tweet about this or Instagram like this without communicating and talking with me,'” he said. “We both just let a lot of things — little things — build up, because we got busy.”

Throughout their relationship, Underwood and Randolph sometimes struggled to incorporate the other into their lives.

“She was doing a lot of things on her own and I was doing things on my own and we forgot what made us so strong together was that communication and working through problems together… being there for one another and being a team,” he said. 

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