A Timeline of Colton Underwood and Cassie Randolph’s Legal Drama: Stalking, Restraining Order, More

Former Bachelor star Colton Underwood and ex-girlfriend Cassie Randolph had a lot of legal trouble following their split in May 2020, including stalking claims and the Huntington Beach native filing a restraining order against her ex. 

The former football player initially announced his split from Cassie on May 29 after weeks of speculation. “It’s been a crazy few months, to say the least, Cass and I have been doing a lot of self-reflecting. Sometimes people are just meant to be friends — and that’s OK,” he wrote in a since-deleted Instagram post. “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.”

The same day, Cassie released her own message about their breakup and admitted it was “one of the hardest things” she’d ever shared on social media.

“Because our relationship is such a public one, our silence on the matter has been speaking for us. Colton and I have broken up but have decided to remain a part of each other’s lives,” the grad student wrote at the time. “With all that we have gone through, we have a special bond that will always be there. I love Colton very much and have an enormous amount of respect for him. We have both learned and grown so much these past couple years and will always have each other’s back. Always.”

However, things took a nasty turn in July after Cassie appeared on The Bachelor: Greatest Seasons Ever. Host Chris Harrison asked the Biola grad about her split from the former leading man, but she remained hush-hush. Her presence on the episode seemingly led Colton to say he “gained so much clarity” while posting about their former romance.

“When our relationship ended, we agreed to handle things as privately as possible as we attempted to navigate our new relationship as friends. I chose to do that since we were living in this interim period, but obviously, a lot changed this week,” he wrote at the time. “I’ve come to realize when you’re in the thick of it you just need to take a step back and look at things from a different perspective.”

Days later, Cassie posted a series of written posts on her Instagram Story begging the Indiana native not to “monetize on their breakup by writing a new chapter” of his book, The First Time. She also claimed he “refused to give [her] any sort of approval” on his version of events.

Things were quiet between the two until September when Cassie filed a restraining order, which revealed how tumultuous their post-split relationship had been.

Keep scrolling to see a timeline of events.