The Bachelor alum Cassie Randolph reportedly tried to break up with Colton Underwood several times prior to their official announcement late last month they've decided to end their romantic relationship.

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The Bachelor Season 23 couple -- who never got engaged and only continued dating after Colton's The Bachelor season wrapped filming in November 2018 -- announced their "mutual" breakup in a pair of Instagram posts last Friday, and an insider told E! News their split was "not surprising" to the people close to them.

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"Cassie was just not as ready for the settled-down life Colton wants right now and she tried to end it a few times," the insider told E! News.

After falling in love with Cassie, Colton told the press on numerous occasions he planned to propose marriage to his girlfriend, and Colton was reportedly ready to get engaged before the end of 2019.

Considering an engagement never happened, fans speculated Cassie wasn't ready and kept pushing back their timeline.

"In truth, the relationship had become more of a friendship than a hot romance," the insider said.

Colton announced on March 20 that he had tested positive for COVID-19, but he eventually made "a full recovery" thanks to Cassie taking care of him.

Quarantining together at Cassie's parents' home in Huntington Beach, CA, in recent months reportedly pulled the blinders off their eyes and made Colton and Cassie realize "they're probably better off as friends."

While both Colton and Cassie came to believe their relationship had run its course, a source told E! News that Cassie was the one to "initiate the conversation," which "upset" Colton.

"[But] it led to both of them being able to be open and honest about what was going on," the source said, adding this conversation took place at least a month ago.

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Around the time of that serious conversation, Colton returned home to his family in Colorado while Cassie stayed with her family in California, a noticeable separation that sparked gossip and breakup speculation amongst fans.
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Both E! News sources said, however, Colton and Cassie intend to stay close since they've been through so much together.

"They really want to remain good friends and hope they can keep each other in their lives," the source added.

Colton and Cassie parted ways after about 18 months together and weeks of not posting about each other on social media.

Back in March, everything seemed fine between the couple, and Colton was once again talking about potentially getting engaged to Cassie.

"We have decided we're not moving in together until we're married. So we have something to look forward to in that step," Colton said on the March 31 episode of Us Weekly's "Here for the Right Reasons" podcast, adding that Cassie has been extremely busy with work and school.

"She still has her internship and some time to put into that and it takes a lot of work for her to do that and takes a lot of her energy and focus. I can't imagine having to plan for a wedding and we still don't want a long engagement. So we want to make sure that timing-wise it's all right."

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In addition, Colton had said on the podcast he and Cassie were definitely "up for" more reality TV.

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"We've both talked about that and we're very hopeful that something might happen. We don't know, but we're definitely onboard with it. I understand the risks involved... but we both like and enjoy being on-camera. I don't see anything wrong with saying that," Colton shared.

"We like opening up when we can and when we feel it's appropriate, so we wouldn't mind it."

In his new memoir, The First Time, Colton admitted he and Cassie briefly split and went their separate ways in August 2019, People reported.

"To put it very frank, after the show, we realized we weren't communicating as well as we once did," Colton revealed in the book that was published in March.

"Nobody was forcing us to talk about real things going on, so we let a lot of things build up... In a weird way, I kind of broke up with myself. I was like, I feel like we need to figure this out and in order to do that, we need space. She agreed. So it was a mutual thing."

Colton became a member of Bachelor Nation when he competed for Becca Kufrin's heart on The Bachelorette's fourteenth season in 2018.

After failing to win her heart, he gave Bachelor in Paradise a shot but then went on to become The Bachelor's Season 23 star.

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When Colton starred on The Bachelor, his season ended prematurely when he fell in love with and selected Cassie over his other two remaining bachelorettes, Tayshia Adams and Hannah Godwin.

Colton had made up his mind before even finishing out his round of overnight Fantasy Suite dates.

Colton had therefore built up a lot of anticipation for his Fantasy Suite date with Cassie, and it seemed he was ready and willing to lose his virginity to her during their romantic evening together.

However, Cassie attempted to quit The Bachelor at that stage in the process because she didn't feel ready to get engaged after dating Colton for such a short period of time.

Colton nearly ended production because he was so devastated, but he fought for Cassie to stay and ultimately convinced her to give him another chance.

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Cassie was hesitant to continue but decided to stick around for Colton now that pressure of an engagement was off the table, and then she proceeded to meet his family on the show and fall in love with him once filming wrapped.

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