Cassie Randolph & Colton Underwood’s Relationship Timeline – Hollywood Life

Cassie Randolph & Colton Underwood’s Timeline: From Fence Jump To Split & More

Look back at Colton Underwood and Cassie Randolphs up and down relationship after he apologized to her on 'GMA.'

Reading Time: 9 minutes

Colton Underwood and Cassie Randolph have been through a lot since they met on season 23 of The Bachelor. The show filmed in 2018, and Cassie and Colton left the show as a couple. The relationship ended after a year and a half, and some drama ensued post-breakup. In April 2021, Colton publicly came out as gay for the first time, and apologized to Cassie for everything he’d put her through. Here’s a timeline of the pair’s relationship:

Colton Meets Cassie on Season 23 of ‘The Bachelor’ 

Colton Underwood and Cassie Randolph
Colton Underwood and Cassie Randolph get to know each other on the first night of ‘The Bachelor,’ season 23, as she teaches him sign language. (Photo credit: ABC)

While Colton had a bevy of beauties to choose from on The Bachelor, Cassie made quite a first impression when she got out of the limo at the mansion when season 23 premiered on ABC on Jan. 7, 2019. Cassie brought along a box of fake butterflies and explained to Colton that she had butterflies in her stomach about meeting the hunk. “I have so many butterflies,” she said. “Literally, I have so many butterflies.”

Cassie then poured them out onto the driveway to show how she got over the jitters and was eager to compete for Colton’s heart. Colton even kept one and showed an Instagram photo holding in his mouth on Mar. 19, after his season ended. While contestant Hannah Godwin got Colton’s first impression rose, Cassie captured his heart for the rest of the season. So much that it led to some MAJOR drama.

Colton Jumps A Fence After Cassie Rejects Him

Despite Cassie being  — no pun intended — on the fence about a future with Colton throughout the show, things came to a head when he and his three finalists visited Portugal for their fantasy suites. Even though Cassie’s main words to Colton were “I don’t know” throughout the season about her feelings for him, Colton was convinced she was the one for him and no other contestant even came close. Instead of a fantasy suite date, they had a tear-filled discussion where Cassie said she wasn’t ready to get married or engaged. Cassie said that, while she loved Colton, she wasn’t 100 percent in love and decided to send herself home.

Cassie said she wanted Colton to “do the best for [him],” and find a woman who loved him and wanted a future, which could have been the other finalists Tayshia Adams or Hannah Godwin. The heartbreak of Cassie not knowing if she could “get there” with Colton caused him to bail on the show by leaving his quarters and literally jumping over a fence to escape the camera crew, Chris Harrison and producers, who were all following him. He would later send both Tayshia and Hannah home and declare, “I think [Cassie] loves me, and I think she’s scared. I came here for love, and I found it, I feel like life without Cassie wouldn’t be complete and I feel that Cassie completes me.”

Cassie Agrees To Date Colton

Cassie Randolph and Colton Underwood
Cassie Randolph and Colton Underwood look happy during ‘After the Final Rose’ on March 12, 2019. Photo credit: ABC.

With Tayshia and Hannah gone, Colton tried to make things work with Cassie, and she agreed to give it another try. He also said he was fine taking it “day by day” with the pretty blonde. Cassie revealed on their final date on The Bachelor that she had a college boyfriend with whom “it got a little controlling,” which led to her hesitations. “I dated someone in college and he had planned out when he was going to propose to me,” she explained. “Then it got pretty controlling. I think that’s why I’m so hesitant to be in a committed relationship.” Umm, red flag alert?

On the March 12, 2019 After the Final Rose, it was revealed that Cassie and Colton were still together after filming wrapped on the season. Cassie said they were “super in love” and Colton told Chris Harrison and viewers, “We still have a lot of room to grow in our relationship. We’re enjoying dating right now.” He also revealed that he has just moved to Los Angeles and the couple was in no rush to move in together. But Colton did give Cassie his final rose, which she accepted, although they did not get engaged.

Cassie and Colton Secretly Break Up & Make Up

Colton Underwood and Cassie Randolph
Colton Underwood holds on tight to Cassie Randolph. They would need that strength during a secret breakup. Photo credit: ABC.

In his 2020 memoir The First Time, Colton revealed that he and Cassie secretly split up in Aug. 2019. “To put it very frank, after the show, we realized we weren’t communicating as well as we once did,” he explained. “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.”

While the split was temporary, Colton wrote that “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 added, “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.” The couple ended up getting back together.

Cassie and Colton Celebrate 1 Year Together

The couple seemed completely in love when they hit their one year dating anniversary mark on Nov. 15, 2019. They took a romantic trip to St. Lucia and Colton professed his love for Cassie in an Instagram post. “I knew then that loving you was going to be easy, but I couldn’t have imagined this…You have shown me the power of love and I never knew that I could love like this… Thank you for making me the happiest man alive. I love all of you, Cass,” Colton wrote in the caption next to a video montage of their cutest PDA moments.

Cassie returned the feelings in her own post, telling Colton, “I can’t believe we’ve already been together for a year. 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.” Hmm…”best friend?” His caption was far more gushy than hers about love.

Colton Contracts COVID-19 While Living With Cassie

While quarantining with Cassie’s family in Huntington Beach, CA in March 2020, Colton tested positive for COVID-19. He spent two weeks isolated in a third floor room at their home “I tested positive and I have been following all of the social distancing rules since last week. My symptoms started a few days ago, I was tested and just received my results today,” he wrote next to a March 20 Instagram video explaining his ordeal. Luckily, Cassie and her family tested negative for the coronavirus.

Fortunately Colton recovered. He told USA Today on March 31 that, “It’s been a crazy last week and a half or so, but I’m feeling a lot better.” He said that the Randolphs had “been sort of my saving grace and they’ve been unbelievably kind to step up and take care of me.”

Colton and Cassie Split For Good

Colton Underwood and Cassie Randolph

Colton Underwood and Cassie Randolph in happier times, attending the 2019 People’s Choice Awards. Photo credit: MEGA.

On May 29, 2020, Colton and Cassie both dropped the news on their respective Instagram accounts that their romance was over. Next to a silhouette photo of the couple looking out at a lake, Colton wrote, “Its 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 okay. 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 shared a series of photos of the former couple and wrote in the caption, “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. 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 others 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 others back. Always.”

Colton and Cassie’s Breakup Gets Messy

In July 2020, Cassie did an interview with Chris Harrison for The Bachelor: The Greatest Seasons — Ever! where she discussed the breakup, but did not go into detail about what happened. Despite Cassie keeping tight-lipped, Colton clearly wasn’t happy with her appearance, and he wrote on Instagram that he would no longer be as “private” about the split anymore. “When our relationship ended we agreed to handle things as privately as possible as we attempted to navigate our new relationship as friends,” he wrote. “I chose to do that since we were living in this interim period, but obviously a lot changed this week.”

Cassie then took to her Instagram page to respond. “Colton, as you know we made an agreement to not publicly discuss our break up. I have honored this, as have you thus far,” Cassie wrote on her Instagram Story. “As some of you may know, I did a GOAT interview this week — I purposefully remained private and vague out of respect for Colton and our relationship.” She also explained that, “I don’t want to make enemies with, or turn my back on the franchise.” Cassie then added, “I would like to place on public record & ask you politely to refrain from discussing our relationship, as we agreed. I would also like to ask that you don’t cloud our great, 1 1/2 year relationship with a messy breakup.” She also asked that Colton “refrain from prolonging our break up, or dragging me, when we both know it’s unwarranted.”

Cassie Gets A Restraining Order

Colton Underwood and Cassie Randolph
While Colton and Cassie looked so happy in this March 2019 photo, he now is not allowed within 100 yards of his ex. Photo credit: MEGA.

After unfollowing each other on Instagram in Aug. 2020, Cassie asked a Los Angeles judge for a restraining order against Colton on Sept. 11, 2020. The request was granted on Sept. 14. Among the things Cassie accused Colton of was attaching a tracking device to her car to allegedly monitor her movements, bombarding her with harassing texts, and showing up uninvited at both her L.A. apartment and her parents’ Orange County home.

The judge granted the temporary restraining order, ordering Colton to stay 100 yards away from Cassie, her home, her car, her job, her parents’ home and her school. He was also not allowed to “harass, attack, strike, threaten, assault (sexually or otherwise),” Cassie, according to the legal paperwork. Cassie also alleged that her relationship with Colton “ended in mid-April 2020,” and that that the alleged stalking incidents began “on or about June 27, 2020” and continued throughout the summer.

In November 2020, Cassie decided to drop the restraining order after she and Colton worked things out privately. “Today, Cassie asked the court to dismiss the temporary restraining order against me,” Colton said in a statement. “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.”

Colton Comes Out As Gay

In April 2021, Colton came out as gay during an interview on Good Morning America. He revealed that he’d known he was gay since he was a freshman in high school, but would “pray” to be straight. During the interview, he also publicly apologized to Cassie. “I would like to say sorry for how things ended,” he revealed. “I messed up. I made a lot of bad choices. [Being gay] made [being in love with Cassie] more confusing for me. I loved everything about her. I wish that i would’ve been courageous enough to fix myself before breaking anyone else.”