From the Fence Jump to a Restraining Order: Inside Cassie Randolph and Colton Underwood’s Journey

First Impressions

Even before the season started, many fans thought that Cassie was going to be a frontrunner. The blonde beauty made quite the entrance when she presented Colton with a box full of butterflies.

“I have so many butterflies,” she said. “Literally, I have so many butterflies.” Colton even put one of the winged creatures in his jacket pocket.

He Saw the Sign

Since she’s a speech pathologist, she decided to teach Colton some sign language. Even though Cassie didn’t receive the first impression rose, she still kissed the Indiana native on night one.

He Wants a Strong Woman

Cassie joined the other girls on a group date, where Colton explained that he is looking for someone who can be his rock. The former football player confessed in his tell-all book, The First Time, that it was the reality babe’s “character and courage” that led him to give her his final rose.

Awkward Moments

In Singapore on their group date, a fortune teller told Cassie that she was Colton’s sister in a past life. The two couldn’t help but laugh about it afterward.

It’s Getting Hot in Here

The two couldn’t keep their hands off each other while they were in Thailand. They made out basically their entire date.

Family Ties

Cassie ended up receiving the final hometown date rose after he questioned their relationship.

Hard Conversations

“I just want you to trust me,” Cassie told her dad during her hometown date.

“I think you need more than a couple of random dates to fall in love with someone,” he said in his confessional. Cassie’s father did not feel comfortable giving Colton his blessing.

Cruising Together

The California beauty explored Portugal with her beau. “Cassie makes me feel complete,” the athlete said during their date.

Uncertain About the Future

Colton told Cassie that her father did not give him his blessing to propose, and the California beauty was a bit shocked to hear that new information.

“I know they want the best for me,” she said about her family. “The fact that they’re not 100 percent sold on Colton and I together kind of freaks me out. It makes me confused if he’s the right person.”

Not Enough Time

Cassie’s dad, Matt, came to Europe to give his daughter some advice after hometowns. “You seemed conflicted,” he said, referring to her not wanting to get engaged.

“I just wish I had more time,” she tearfully told her father. “I don’t want it to be over with him, but it scares me that at the end it’s accepting a proposal, that’s huge. But I’m not ready for it to be over.”

A Tough Decision

Before her fantasy suite date with Colton, she confessed that she was going to send herself home. “Today was perfect, and I love you so much,” she said. “After today, I’m not like, in love. I don’t know why after today, I’m not … I feel like I’m having doubts about it.”

Not a Happy Ending

Colton wanted to fight for their relationship, and he even was willing to wait for her. Unfortunately, it was too much pressure for the ESL teacher and she left the show.

A Shocking Twist

The leading man eliminated Hannah G. and Tayshia in order to pursue a relationship with the California native. “I am willing to do anything and everything because that is how much I love Cassie,” Colton said before he knocked on her door.

Kiss and Make Up

Cassie was surprised when Colton showed up, but he revealed that he needed to tell her something important. “I am asking for a second chance to take it day by day and figure it out,” the former football player said.

“This is crazy, this is really crazy. I can’t believe you did that,” she told him. Then, Colton asked her if she would join him in Spain so that she could meet his parents. Fortunately, she said yes!

Facing Her Fear

After some serious conversations, Cassie explained her greatest fear in all of this. “I dated someone in college and he had planned out when he was going to propose to me and then it got pretty controlling,” she said. “You have to change everything for this one person. I know it’s not true, but it’s just something that is so ingrained in me.”

The Next Step

After the duo went to dinner, they decided to give the fantasy suite another shot. Cassie also told Colton she’s “all in.”

“I am excited to see where our relationship can go,” he dished. “I have always said I am waiting to be in love with someone, the right person, and I hope that person is Cassie. If the moment is right and if it’s right for us to take the next step in our relationship, then it could happen tonight.”

On the Same Page

So, did Colton and Cassie do the deed? “Last night was absolutely incredible, and I feel like a new man,” he said. “We did what was best for our relationship and we grew as a couple. We had a great time last night.”

After many ups and downs, Colton revealed that he and Cassie were finally on the same page. “I can’t wait to wake up to her over and over again,” he dished.

Happily Ever After

The lovebirds made their first debut as a couple on After the Final Rose. “We’re in love. We’re super in love,” she exclaimed.

“We still have a lot of room to grow in our relationship right now, so we’re enjoying dating right now,” Colton said. Colton revealed that he moved to Los Angeles to be near Cassie. He noted in his book that they were waiting until marriage before living together.

Rocky Waters

Colton revealed in his book that he and Cassie briefly split in August 2019. “To put it very frank, after the show, we realized we weren’t communicating as well as we once did,” he explained about the strain on their relationship. “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.”
Although their uncoupling lasted less than a couple of days, it taught them some invaluable lessons. “It was a very real and very emotional breakup, but it was also very good to be real and emotional because it forced us to have conversations and move on. Now, we know the flags to look for,” he wrote. “When issues start to creep up, it’s like, let’s go have a conversation. We’re trying to be more transparent and honest and really trust each other.”

One Year Strong

Despite it all, Colton and Cassie celebrated their one-year anniversary on in November 2020.
“I knew then that loving you was going to be easy, but I couldn’t have imagined this,” the Bachelor Nation stud gushed over his girlfriend at the time. “You have shown me the power of love and I never knew that I could love like this. I secretly love when you correct me when I mispronounce words or when I leave a mess in the kitchen and you make me clean it up. I love all of the small moments in our life just as much as the big ones. Thank you for making me the happiest man alive. I love all of you, Cass.”
The feeling was mutual, and the ESL teacher penned her own message to her beau. “I can’t believe we’ve already been together for a year,” she wrote. “It was full of lots of changes, growth, and a million amazing memories with you … I am the luckiest girl. I couldn’t ask for anything more than to have a man like you by my side. You mean the world to me. I love you, best friend … Now let’s get another Sangria.”

Coronavirus Diagnosis

While quarantined with Cassie’s family in Huntington Beach, California, Colton revealed he tested positive for coronavirus. Cassie was super supportive and helped nurse him back to health. “They have been amazing and have been taking great care of me,” Colton wrote of her brood.

Birthday Wishes

Just one month before publicly announcing their breakup, Colton posted a message for Cassie’s birthday.

“Happy 25th birthday, Cass. There are a million things I can say here about how great you are, but I’d rather keep that between us,” he wrote. “Thank you for being you and letting me share this last year with you. I’m a better man for loving you. Can’t wait to make more memories.”

Colton Goes to Colorado

Less than two weeks later, Colton left the Randolph residence to continue quarantining with his family in Colorado.

Colton’s Breakup Announcement

On May 29, Colton took to Instagram to announce his split from Cassie. “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. 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 Confirms

Cassie posted her own message the same day. “First off, I want to say this is one of the hardest things I have had to share as neither one of us is quite ready to talk about it yet,” she wrote. “However, 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. 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.”

Cassie Slams Fans for Hating on Their Split

“I feel like saying: OK all you mother ffers hating on me for my breakup. Please stop. It’s been an awful few months for ME trying to go [through] it,” she shared on Instagram on July 1.

Back on ‘The Bachelor’

Cassie called out her “edited” interview after appearing on The Bachelor: Greatest Season Ever on July 6. “I’ve said this a million times, you guys cannot judge something that you know is edited and know nothing about … There was so much more that I talk about in that interview than just our relationship,” she said on her Instagram Story. She noted she “said nothing” during her interview with Chris Harrison, despite getting hate from fans.

Colton Speaks Out

Colton shared his own statement on July 9 via Instagram. “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 following her Bachelor appearance. “If you’ve been kind enough to have followed our story you’ve been with us through all of the ups and downs which have taught me so many lessons. 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.”

The former football player added that he’s “gained so much clarity” about what he “needs in a relationship.”

Her Response

Cassie responded to Colton’s shady Instagram post on July 10. The Bachelor Nation babe went on “public record” to ask her ex not to “monetize their breakup by writing a new chapter” to his book, The First Time: Finding Myself and Looking for Love on Reality TV. She also claimed he “refused to give [her] any sort of approval” on his version of events.

A Restraining Order

Cassie filed a restraining order against Colton on Friday, September 11, Life & Style confirmed. In it, she accused her former beau of stalking her, tracking her car, and harassing her and her friends from an anonymous phone number.

Back on Good Terms

Two months later, in November 2020, Cassie dropped her restraining order.

“Today Cassie asked the court to dismiss the temporary restraining order against me,” Colton told TMZ. “The two of us were able to reach a private agreement to address any of Cassie’s concerns. I do not believe Cassie did anything wrong in filing for the restraining orders and also believe she acted in good faith. I appreciate everyone’s respect for privacy regarding this matter.”

Reliving the Pain

Colton shared his take on the breakup in January 2021, when he added a new chapter to his 2020 memoir, The First Time.  He recalled Cassie first trying to break up with him following his bout with Covid. “She took me aside and told me she was struggling with everything in our relationship and didn’t know what to do,” he said. “My head spun like one of those characters in a cartoon. What? She was struggling with everything?”

They stayed in contact for awhile while Cassie tried to figure out her feelings. “Our conversations were delicate check-ins,” he wrote. “We were friendly but real. She wanted to talk about how to move forward and remain friends, while I held on to hope that we could get back together after some time passed. Finally, Cass called and said she wanted us to make a public statement about our breakup.”

That’s It

The pair met up once more but Colton says he understood it was over. “Afterward, she came back to my place, where we had a few drinks, hung out, and we were Colton and Cass again the rest of that night,” he said. “Then, when we woke up the next morning, I could tell everything was different. I had the urge to say I love you before she walked out the door, and I sensed she did, too. No door shut that softly has ever made a louder sound.”

Brief Response

Following Colton’s big news, Cassie stayed relatively hush-hush about the situation but briefly spoke on it during a YouTube video on April 22.

“I don’t want to get into anything, I just want to say thank you so much for all the kind comments and messages from you guys. I really appreciate it,” she said. “Regarding the topic in the media that brought my name up this week, I just want to let you know that I’m not going to be further discussing or commenting on it for now. There’s a lot of layers to it and I just feel that the best thing for me at this time is to move forward and just for us on going forward.”

The California native added, “So, if I do decide in the future to say anything or make a comment, you guys will be the first to know but for now, I just wanted to say thank you … I feel very loved and supported.”