By Bayo Olupohunda,Night Mongina
Copyright legit
Colton Underwood and Cassie Randolph’s relationship began on The Bachelor in 2019 and lasted until May 2020. Their time together was marked by highs and lows, including a messy break-up that resulted in a restraining order.
Key takeaways
Colton and Cassie met on The Bachelor in 2019.The couple briefly broke up in August 2019 but got back together soon after.In May 2020, they announced their split, saying it was a mutual decision.Months later, Cassie filed a restraining order against Colton, which she later dropped.
Profile summary
Colton Underwood and Cassie Randolph’s relationship timeline
Cassie and Colton’s relationship was one of the most talked-about romances to come out of The Bachelor. From their first meeting on the show to their highly publicised breakup, their story had plenty of ups and downs. Here is a closer look at the key moments in their relationship timeline.
January 2019: Colton and Cassie first met on The Bachelor
Colton Underwood and Cassie Randolph met during the premiere of the American dating and relationship reality television series The Bachelor. Randolph brought a box of butterflies.
February 2019: The pair enjoyed a romantic date in Thailand
In February 2019, Colton and Cassie went on a one-on-one date in Thailand. They spent time talking on a boat and really got to know each other better. After dinner, they cuddled in bed, and Colton told Cassie that he was really into her and crazy about her.
February 2019: Colton met Cassie’s family in Huntington Beach
During hometown dates, Colton met Cassie’s family in Huntington Beach. Her father, Matt Randolph, did not give his blessing, saying Cassie was not ready for marriage. Cassie also hadn’t said “I love you,” which made Colton anxious about her feelings.
March 2019: Colton’s fence jump followed Cassie’s decision to leave
During the show, Randolph initially eliminated herself, stating she was not ready for an engagement. Underwood famously jumped a fence in response and pursued her, and later broke up with the other women to try to win Cassie back.
March 2019: Colton and Cassie left The Bachelor as a couple
At the finale in March 2019, Colton asked Cassie to stay with him, even though they were not ready to get engaged. Cassie agreed, and they decided to leave the show together as a couple. Instead of rushing into marriage, they chose to take things slowly and enjoy their relationship at their own pace.
May 2019: The ex-couple confirmed they were taking things slow
In May 2019, Colton Underwood and Cassie Randolph shared with Us Weekly that they were not rushing into an engagement or moving in together. They emphasised that they were enjoying their relationship and not focusing on a specific timeline. Cassie stated,
We really don’t have a timeline. We’ve definitely talked about it, but we’re just enjoying right now and not worrying about it.
August 2019: Colton and Cassie briefly broke up
In August 2019, Colton Underwood revealed in his memoir, The First Time, that he and Cassie Randolph briefly split for a few days due to communication issues. He explained that after the show, they realised they were not communicating as well as they once did, and things started to build up. Colton described the breakup as mutual, stating,
To put it very frankly, after the show, we realised we weren’t communicating as well as we once did. 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.
November 2019: Colton and Cassie celebrated their first anniversary
In November 2019, Colton Underwood and Cassie Randolph celebrated their first anniversary. They travelled to St. Lucia to mark the occasion. Colton shared a heartfelt message on a now-deleted Instagram post, writing:
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. Thank you for making me the happiest man alive. I love all of you Cass.
March 2020: Colton battled coronavirus with Cassie by his side
In March 2020, Colton Underwood tested positive for coronavirus. He had to stay in quarantine, and Cassie Randolph took care of him while he recovered.
May 2020: Colton and Cassie officially ended their relationship
In May 2020, Colton Underwood and Cassie Randolph announced they had broken up. They shared the news on a now-deleted Instagram post, emphasising that their split was friendly. Cassie wrote that they would still be part of each other’s lives, saying,
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 of years, and we will always have each other’s back. Always.
July 2020: Colton and Cassie’s breakup turned messy
In July 2020, Colton Underwood and Cassie Randolph’s breakup turned messy. Cassie appeared on The Bachelor: The Greatest Seasons Ever!, which Colton felt went against their agreement to keep things private. He was also concerned that Cassie planned to include details about their breakup and his COVID recovery in a new chapter of her book without his approval. He wrote,
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).
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.
Cassie accused him of trying to profit from the split, while Colton’s representative denied her claims, per US Weekly.
September 2020: Cassie filed a restraining order against Colton
In September 2020, Michelle Randolph’s sister filed a restraining order against Colton Underwood. She said he had put a tracking device on her car, sent harassing texts, and showed up at her flat and her parents’ house without permission after they broke up.
The court granted the order, requiring Colton to stay at least 100 yards away from her and not contact her.
October 2020: Cassie filed a police report over a tracking device
In October 2020, according to TMZ, Cassie Randolph filed a police report against Colton Underwood about the tracking device she found on her car. On 6 October, both of their lawyers went to court for a hearing.
They told the judge they were trying to solve the issue peacefully. The judge then extended the restraining order until their next hearing on 6 November 2020.
November 2020: Randolph dropped the restraining order against Underwood
In November 2020, Cassie Randolph dropped the restraining order against Colton Underwood after they reached a private agreement. Colton said he believed Cassie was acting in good faith. The case was settled privately, and the restraining order was officially removed.
April 2021: Colton Underwood publicly came out as gay
In April 2021, Colton Underwood publicly came out as gay during an interview on Good Morning America. He said he was deeply in love with Cassie Randolph at the time, which made understanding his own sexuality very confusing. He said:
This year’s been a lot for a lot of people, and it’s probably made a lot of people look at themselves in the year and figure out who they are. I’ve run from myself for a long time, I’ve hated myself for a long time. I’m gay. I came to terms with that earlier this year, and the next step in all of this was sort of letting people know. … I’m the happiest and healthiest I’ve ever been in my life. That means the world to me.
Colton also apologised for the way their breakup happened, saying,
I’m sorry for any pain and emotional stress I caused. I wish that it hadn’t happened the way that it did. I wish that I had been courageous enough to fix myself before I broke anybody else.
December 202: Colton Underwood apologised to Cassie
In December 2021, Colton Underwood starred in the Netflix documentary Coming Out Colton, where he shared his journey of coming out and talked about his past relationship with Cassie Randolph. He apologised again for the legal issues with her and said the restraining order was a wake-up call that pushed him to come out. Colton explained,
I think that was sort of a huge wake-up call… I wish I had dared to come out without having to be pushed.
What happened with Colton and Cassie? The two dated after The Bachelor in 2019, broke up in 2020, and later faced a legal dispute before moving on separately.How long did Colton and Cassie date? The TV personalities dated for about a year and a half, from spring 2019, after The Bachelor, until their breakup in May 2020.Does Colton Underwood have a baby? The former football player has a son, Bishop Colton Brown-Underwood, who was born through surrogacy in September 2024.Who is the biological dad of Colton Underwood’s baby? Bishop Colton Brown-Underwood’s biological dad is Jordan C. Brown, Colton’s husband.Did Cassie and Colton get engaged? Colton and Cassie never got engaged.Did Colton ever apologise to Cassie? The reality star apologised to Cassie multiple times for how he handled their breakup and the legal issues that followed.
Colton Underwood and Cassie Randolph’s relationship journey was filled with love, challenges, and public scrutiny. Their relationship began on The Bachelor in 2019 and officially ended in 2020 after a public breakup and legal dispute. Underwood later publicly came out as gay, apologising for the pain caused during their breakup.
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