Colton Underwood and Cassie Randolph’s Relationship Timeline

Credit: ABC (2); Courtesy of Cassie Randolph/Instagram (2)

Colton Underwood and Cassie Randolph's Relationship Timeline

Another Bachelor Nation love story has come to an end. Colton Underwood and Cassie Randolph didn't have the traditional romance — or even the traditional Bachelor timeline. However, from the moment they met on the season 23 Bachelor premiere, the pair were connected. Although their onscreen journey wasn't an easy one (the fence jump!), they began a real relationship after the cameras stopped. “It was a lot of changes, for sure, because we went from these more simple, more normal lives and then all of a sudden, we film a show and then you’re thrown into craziness where everyone is very hyperaware of everything that goes on in your life and your relationship,” the speech pathologist told Us Weekly exclusively in October 2019. “It was a little bit of a struggle at first, I think — like adjusting to everything. But I feel like now we’ve kind of gotten used to it and learned to balance everything a lot more.” The former NFL player also noted that the show actually helped them grow their relationship. “I think you learn to communicate too,” he explained. “Just with whether it’s tabloids or someone speculating a certain thing or people reading into your body language, you know. You just learn how to communicate with each other and you’ll be on the same page with everything going on. ... Nobody could ever prepare you for what life is like after that. Like, you can have people tell you all you want, like, ‘Oh, wait for this, wait for this.’ But until you’re in it, you don’t really get the full magnitude of it." [jwplayer ENFLckLm-l3ahXupL] Colton later revealed that while he got a great outcome, he felt a bit "burnt" by the shows' producers. “They always asked to rank the girls. And very early on, Hannah [Godwin] was up there. And she got left off of a date,” he said in August 2019. “I sort of recall remember feeling a little burnt when they did that. I was like, ‘So let me get this straight. Hannah’s No. 1 on my list right now, and she’s not getting a date this week?’” He then decided to change things: “From there on out, I was like, ‘All right, if you’re going to do that to my top girls, I’m not really going to tell you who my top girls are, because I don’t want you messing with them.' So in a weird way, I tried to defend myself and defend the girls by not being truthful to them who my top was." However, in May 2020, the pair announced that they had split. Scroll through the gallery below for a full timeline of Colton and Cassie's relationship: [podcast_block]

Credit: ABC/Rick Rowel

January 2019

During the premiere, Colton and Cassie met in front of the mansion and she brought a box of butterflies.“I have so many butterflies. Literally, I have so many butterflies," she said and he put one in his jacket pocket.

Credit: ABC/Rick Rowel

January 2019

During week 4 of The Bachelor, the group went to Singapore and got their fortunes read. The woman told Cassie she was Colton’s sister in a past life!

Credit: ABC

February 2019

During a one-on-one date in Thailand, the pair went on a boat ride together. They had many important conversations and after dinner, they crawled in bed together to cuddle and he told her he was crazy about her.

Credit: ABC/Rick Rowel

February 2019

During hometown dates, Colton met Cassie's family. Cassie's dad was very skeptical of Colton. In fact, he was the only one who didn't give Colton his blessing to propose to Cassie. She also wasn't sure how she felt and he was worried after she didn't drop the L-word.

Credit: ABC

March 2019

During week nine, her dad returned to have a talk with Cassie about her future with Colton. She was extremely torn and told Colton she loved him but isn't ready to be engaged. He said that she's The One, but she wasn't sure she can move on — she loved him but isn't fully in love. In turn, she chose to leave. Colton was so upset that he jumped over a fence and tried to leave the show.

Credit: ABC/John Fleenor

March 2019

During the finale, Colton ended things with the other women and went to Cassie's hotel room to tell her she's the only one left. She decided to give their relationship a chance. During the live aftershow, Colton revealed he moved to Los Angeles to live closer to Cassie.

Credit: Courtesy of Vegas Golden Knights

March 2019

Less than two weeks later, the couple traveled to Las Vegas and Cassie wore a jacket that read "Future Mrs. Underwood" on the back.

Credit: Jeff Christensen

May 2019

A few months later, the pair revealed exclusively to Us that they were not going to "rush" into an engagement or moving in together. "We really don’t have a timeline," she said at the time. “We’ve definitely talked about it, but we’re just enjoying right now and not worrying about it.”

Credit: Courtesy of Cassie Randolph/Instagram

June 2019

The couple traveled to Bermuda over the summer and shared multiple PDA-filled pics from their trip.

Credit: Shutterstock

August 2019

In Colton's book, The First Time, he revealed that he and Cassie briefly split over the summer. However, it only lasted a few days as he missed her too much.

Credit: Courtesy of Colton Underwood/Instagram

November 2019

The couple celebrated their first anniversary in November, heading to St. Lucia together.

"One year ago today they put the cameras down and we cooked our first meal together in Mallorca, Spain. 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," he wrote on Instagram at the time. "Thank you for making me the happiest man alive. I love all of you Cass."

Credit: Courtesy of Cassie Randolph/Instagram

March 2020

When Colton tested positive for coronavirus, he became quarantined at Cassie's home and she took care of him until he felt better.

Credit: AFF-USA/Shutterstock

May 2020

The pair revealed via Instagram posts that they had decided to break up. "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," she wrote. "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."

Credit: CraSH/imageSPACE/Shutterstock; Jordan Strauss/Invision/AP/Shutterstock

July 2020

The duo’s split turned messy after Colton shaded Cassie’s decision to appear on The Bachelor: The Greatest Seasons Ever! in July 2020. While she didn’t give many details of their breakup during her interview with Chris Harrison, the football player took to Instagram to reiterate that they agreed to handle their breakup privately. As a result, Cassie fired back and accused Colton of planning to profit off their split with a new chapter in his book, The First Time.

“You informed me you intend to monetize our breakup by writing a new chapter to discuss your experience with COVID (where you stayed in my family’s house during your recovery and about our breakup),” he wrote. “You have also refused to give me any sort of approval on the chapter you will be writing, which will heavily feature me … This seems a bit unfair to me. Colton, you can do what you want, but please do not have a double standard. … It seems you are subtly engaging in a tactic that peppers in aggressive comments such as ‘that obviously changed this week’ in order to make me look like the bad one.”

Colton’s rep told Us at the time that Cassie’s accusations were “simply not true.”

Credit: Stewart Cook/Shutterstock; Jason Merritt/Radarpics/Shutterstock

August 2020

While Colton claimed he and Cassie were on OK terms during an appearance on Reality Steve’s podcast in August 2020, she unfollowed him on Instagram later that month. Colton subsequently stopped keeping up with his ex on the social media platform. Cassie’s sister, Michelle, and Michelle’s boyfriend, Gregg Sulkin, also unfollowed him at the time.

Credit: Courtesy of Cassie Randolph/Instagram

September 2020

News broke in September 2020 that Cassie filed a restraining order against Colton, claiming he had planted a tracking device in her car, harassed her via text message and showed up uninvited to her apartment and her parents’ house after their breakup. The order was granted, forcing him to stay at least 100 yards away from her and to not contact her.

Credit: Shutterstock (2)

October 2020

Hours before their scheduled court appearance, Cassie filed a police report against Colton over the tracking device that he allegedly planted in her car.

Us confirmed on October 6, 2020, the exes’ respective attorneys attended the hearing. After both lawyers told the judge that they are “trying to resolve” the issue between their clients “amicably,” the order was extended until their next hearing on November 6, 2020.

Credit: Danny Moloshok/Invision/AP/Shutterstock

November 2020

Underwood revealed that the case had been settled in private and the restraining order was dropped in November 2020.

Credit: John Salangsang/Shutterstock

April 2021

In an emotional interview on Good Morning America, Underwood came out as gay. He also explained that he was very much in love with Randolph, which made the process even more confusing, and apologized for their messy breakup.

"I’m sorry for any pain and emotional stress I caused," he shared. "I wish that it wouldn’t have happened the way that it did. I wish that I had been courageous enough to fix myself before I broke anybody else."

Credit: Netflix

December 2021

Underwood apologized once again for the legal situation with Randolph during his Netflix series, Coming Out Colton, which debuted on December 3. He shared with Us ahead of the premiere that he may not have come out if the restraining order hadn't happened.

“I think that was sort of a huge wake-up call. I’m sad that it even got to that point to where that had to be my wake-up call and me affecting other people in my life was sort of the moment that I realized I had to come out,” he said. “Obviously, I wish I would have had the courage to come out without having to be pushed.”

Although Randolph was asked to be part of the series, she declined. Due to legal restraints, he was unable to give her a heads up before the show dropped.