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Colton Underwood and Cassie Randolph’s breakup is getting messier by the day. The former Bachelor couple went from being lovebirds, talking about engagement to not even being allowed to be in the same room. Despite already being granted a temporary restraining order, Randolph just went to the police and filed a new complaint against her ex.

Cassie Randolph and Colton Underwood
Cassie Randolph and Colton Underwood | Jerod Harris/Getty Images for Tubi

What happened between Colton Underwood and Cassie Randolph?

Underwood and Randolph didn’t have your typical Bachelor love story. In fact, Randolph actually tried to send herself home before the season was over. But somehow, Underwood was able to calm her down and the two ended the season together. The pair dated for almost two years. During that time, they got so close that Randolph’s family even took care of Underwood while he recovered from coronavirus (COVID-19).

But in May, the two announced their split.

“It’s been a crazy few months to say the least, Cass and I have been doing a lot of self-reflecting,” Underwood wrote on Instagram at the time. “Sometimes people are just meant to be friends – and that’s OK. We both have grown immensely and been through so much together – so this isn’t the end of our story, it’s the start of a whole new chapter for us.”

Cassie Randolph’s restraining order

On Sep. 11, things got a bit uglier as Randolph filed for a restraining order against Underwood after receiving a number of strange text messages from random numbers. In the initial documents obtained by HollywoodLife, it states that Underwood has to stay 100 yards away from Randolph, her home, her parents’ home, her school, her car, and her job. He must not “harass, attack, strike, threaten, assault (sexually or otherwise)” Randolph.

“Mr. Underwood admitted that he was the one who put the tracker on her car and had been the one sending text messages to her, her friends, and himself, under the alias phone numbers,” the document reads.

Cassie’s new police report against Colton Underwood

Though things seemed to calm down for a moment, Randolph filed a new claim with the LA County Sheriff’s office on Sep. 30. This time alleging that Underwood put a tracking device on her vehicle.

“A female victim entered the West Hollywood station lobby on Wednesday, September 30th, 2020, to report an unlawful use of tracking device on her vehicle. A counter report was authored and a detective assigned to investigate the case,” the sheriff’s office told the outlet. “Due to the nature of this ongoing investigation, no other information is available at this time.” 


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How does Colton Underwood feel about all of this?

Despite all of this, Underwood is still struggling with the breakup.

“[Colton] really isn’t ready to accept it yet and would love nothing more than to get Cassie back,” a source previously told HollywoodLife. “He is gutted that all of this is happening in front of the whole world.

“He hates that it has gotten to a place where she has filed a restraining order against him as he would love to just have a conversation with her to figure out their differences,” the source continued.