Colton Underwood & Cassie Randolph: Relive Their Relationship Through The Years

By:

Medina Lynn, Julia Teti

May 12, 2021 1:30PM EDT

With the new season of ‘The Bachelorette’ just weeks away, take a look back on another former Bachelor Nation couple’s romantic timeline: Colton Underwood and Cassie Randolph.

1 of 27

Colton Underwood & Cassie Randolph

Colton Underwood & Cassie Randolph — Cassie Randolph and Colton Underwood stunned on the red carpet at the 54th Annual ACM Awards in Las Vegas on April 7, 2019. Cassie wore a silver and black deep v-neck dress, while Colton rocked an all-black suit.

The couple found each other on Colton’s season of ‘The Bachelor’ in 2019, in which Cassie actually left during the Fantasy Suites episode since she thought things were moving too fast. Cassie was unsure if she could get engaged at the end of the season, so she wanted Colton to have that chance with one of the other women, since she knew that was what he wanted. Colton, however, wanted to be with Cassie, so he jumped a fence and ‘left the show’ to find her. The two reconciled, and decided to ‘just date,’ with Cassie meeting Colton’s family in Europe.

After more than one year together, Cassie and Colton ended their relationship. Their breakup wasn’t easy on either of the reality TV stars, and circumstances took a dramatic turn that no one saw coming. Revisit their romance with this comprehensive timeline.

2 of 27

Colton Underwood & Cassie Randolph Meet

Colton Underwood & Cassie Randolph Meet — Cassie Randolph and Colton Underwood met on the 2019 season of ‘The Bachelor,’ on which Colton was the lead. The couple were immediately smitten, and Cassie stood out from the crowd for her fun-loving spirit and how she made Colton feel totally at ease.

3 of 27

Colton Underwood & Cassie Randolph’s Relationship Grows

Colton Underwood & Cassie Randolph’s Relationship Grows — Colton Underwood and Cassie Randolph’s relationship clearly started to flourish on the show, but it wasn’t met without some drama. Cassie’s integrity was called into question, as was fellow contestant Caelynn Miller-Keyes. Rumors in the house of women spread that the two weren’t there for the right reasons. But Colton stood his ground.

4 of 27

Colton Underwood & Cassie Randolph’s Romance Heats Up

Colton Underwood & Cassie Randolph’s Romance Heats Up — Cassie Randolph really had a lot of love for Colton. The physical chemistry between the two was evident, and she remained a contestant on the show for weeks! From group dates to one-on-ones, it was clear that Cassie was Colton’s front-runner.

5 of 27

Cassie Joins Colton’s Final Three

Cassie Joins Colton’s Final Three — Colton made the decision to narrow down his group to three final women: Tayshia Adams, Hannah Godwin, and Cassie. During their gorgeous trip to Europe, Colton finally reached the decision he couldn’t go on without Cassie, even though she was hesitant to go through with an engagement at the end of the process. That’s when things turned dramatic.

6 of 27

Colton Jumps The Fence

Colton Jumps The Fence — Colton literally jumped a fence once Cassie made the decision to leave. He couldn’t be found for some time, until hours later when the crew found him. Colton was totally shaken, but knew he couldn’t go through the process without Cassie. He finally sought out Cassie.

7 of 27

Colton & Cassie Keep Their Love Alive

Colton & Cassie Keep Their Love Alive — Colton convinced Cassie to stay, telling her that he had broken off his relationships with Tayshia and Hannah, and reassuring her that there was no pressure to get engaged at the end of the show. Cassie, though reluctant, stayed with Colton and met his family.

8 of 27

Colton & Cassie On ‘After The Final Rose’

Colton & Cassie On ‘After The Final Rose’ — Cassie and Colton were completely united while attending the taping for the ‘After The Final Rose’ special. The two were very much in love and focused on dating one another and having fun away from the cameras. Here, Cassie Randolph wipes lipstick away from Colton Underwood’s face after they share a kiss during ‘After the Final Rose’ following ‘The Bachelor’ finale. Colton playfully let her do so.

9 of 27

Colton & Cassie Go Public

Colton & Cassie Go Public — Following their ‘After The Final Rose’ episode, Colton and Cassie let their love shine out in the open. Here, Colton Underwood and Cassie Randolph hold hands while leaving ‘Good Morning America,’ where they talked about their relationship and ‘The Bachelor. Cassie wore a polka dot dress while Colton rocked a suit.

10 of 27

Colton & Cassie At ‘GMA’

Colton & Cassie At ‘GMA’ — Colton Underwood and Cassie Randolph are all smiles as they head to ‘Good Morning America’ after the finale of ‘The Bachelor.’ The couple enjoyed walking hand-in-hand publicly, finally.

11 of 27

Colton & Cassie Doing Press In NYC

Colton & Cassie Doing Press In NYC — Colton Underwood and Cassie Randolph held hands and looked so in love as they arrived to the Build Speaker Series on March 13, 2019. Cassie wore a floral dress to the taping. The two were all smiles during this time in their relationship, where they could be a normal couple, talk about their romance, and not worry about being constantly followed by cameras — or handing out any roses.

12 of 27

Colton & Cassie On A Date At The Beach

Colton & Cassie On A Date At The Beach — Once Colton and Cassie settled into their romance, the two enjoyed some fun dates during spring in 2019. Here, Colton Underwood and Cassie Randolph enjoy a sunny date while on a date together in Huntington Beach, California on March 16. Cassie rocked a white mini dress.

13 of 27

Colton & Cassie Share A Kiss

Colton & Cassie Share A Kiss — Colton Underwood and Cassie Randolph are spotted kissing while laying out by the beach on March 16. Cassie simultaneously was looking for something in her purse.

14 of 27

Colton & Cassie At The ACM Awards

Colton & Cassie At The ACM Awards — While Cassie and Colton were keeping their relationship fairly low-key, that didn’t stop them from attending major events and showing off their love for one another. Here, Cassie Randolph and Colton Underwood posed on the red carpet for the 2019 ACM Awards on April 7, 2019. Cassie wore a silver and black dress with silver high heels.

15 of 27

Colton & Cassie At ‘Go Binge Yourself’ Event

Colton & Cassie At ‘Go Binge Yourself’ Event — As 2019 went into the summer months, Colton and Cassie were still going strong. Here, Colton Underwood and Cassie Randolph couple up at Tubi’s ‘Go Binge Yourself’ Newfront in New York City on May 1, 2019. Cassie looked gorgeous in her slinky dress, while Colton rocked a white button down.

16 of 27

Colton Hugs Cassie Behind The Scenes Of ‘Famous’ Music Video

Colton Hugs Cassie Behind The Scenes Of ‘Famous’ Music Video — Things were still going well for Colton and Cassie, and the two kept the spark alive! Colton Underwood was captured hugging Cassie Randolph in a private moment behind the scenes of Adam Doleac’s ‘Famous’ music video.

17 of 27

Colton Smooches Cassie On The Set Of Adam Doleac’s ‘Famous’ Music Video

Colton Smooches Cassie On The Set Of Adam Doleac’s ‘Famous’ Music Video — Cassie Randolph and Colton Underwood were all smile behind the scenes of Adam Doleac’s music video for ‘Famous.’ The two starred in the video, which they said resonated with their own love story.

18 of 27

Colton & Cassie At The 2019 People’s Choice Awards

Colton & Cassie At The 2019 People’s Choice Awards — Cassie Randolph and Colton Underwood share a sweet smooch on the red carpet of the 2019 People’s Choice Awards. The cute couple and former ‘Bachelor’ stars had a fun night showing off their love!

19 of 27

Colton Underwood & Cassie Randolph At The People’s Choice Awards

Colton Underwood & Cassie Randolph At The People’s Choice Awards — Cassie and Colton’s love was still going strong as they attended the 2019 People’s Choice Award. Cassie Randolph and Colton Underwood attended the 2019 People’s Choic Awards in Los Angeles. Cassie looked stunning in her plunging dress, while Colton was handsome in his black suit.

20 of 27

Colton & Cassie At The 53rd Annual CMA Awards

Colton & Cassie At The 53rd Annual CMA Awards — As the year went into fall, Colton Underwood and Cassie Randolph continued to attend events, proving that they were still very much an item. Here they are at the 53rd Annual CMA Awards at the Bridgestone Arena in Nashville on November 13, 2019.

21 of 27

Colton Underwood Seen After Recovering From COVID-19

Colton Underwood Seen After Recovering From COVID-19 — Colton Underwood and Cassie Randolph are seen hanging out on her parents balcony in Huntington Beach, CA on Saturday, April 4. The former ‘Bachelor’ was in great spirits as he chatted with Cassie and an unidentified female friend outside his home. Colton tested positive for the coronavirus just two weeks prior, confirming just days ago that he was feeling ‘so much better.’

22 of 27

Colton Underwood Walks With The Randolph Sisters

Colton Underwood Walks With The Randolph Sisters — While quarantining with the Randolph family in Orange County, Colton Underwood steps out for a stroll with Cassie Randolph and her sister Michelle on April 7, 2020. They’ve all been isolating together in Cassie’s parents’ home in Huntington Beach amid the coronavirus pandemic. The two later went their separate ways one month later in May 2020.

23 of 27

Cassie Randolph’s Car Tracking Device

Cassie Randolph’s Car Tracking Device — By the summer of 2020, things between Cassie and Colton took a turn. The couple endered their relationship, but Colton’s behavior became incredibly troubling. He allegedly stalked Cassie after their split, and even allegedly planted and tracking device on her car. In the restraining order request, Cassie claimed that Colton put a tracking device on her car after they broke up. She shared a photo of it in the paperwork.

24 of 27

Colton Underwood’s Alleged Car Tracking Device

Colton Underwood’s Alleged Car Tracking Device — Colton Underwood’s alleged car tracking device that he placed on Cassie Randolph’s car as seen in her restraining order request. A judge granted it on Sept. 14, 2020.

25 of 27

Cassie Randolph’s Restraining Order Request

Cassie Randolph’s Restraining Order Request — Cassie Randolph’s allegations against Colton Underwood, as explained in her restraining order request. A judge granted it on Sept. 14, 2020.

26 of 27

Cassie Randolph Accuses Colton Underwood of Stalking

Cassie Randolph Accuses Colton Underwood of Stalking — In he restraining order request, Cassie claimed that Colton was stalking her, sending harassing texts and more. She was granted her restraining order by a Los Angeles judge on Sept. 14, 2020.

27 of 27

Colton Underwood & Cassie Randolph Today

Colton Underwood & Cassie Randolph Today — As of 2021, Colton Underwood and Cassie Randolph don’t appear to stay in touch at all. Months after their breakup, Colton made the decision to come out, revealing that he is gay. Upon reflecting on their relationship, Colton had this to say: “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 explained, adding, “I appreciate everyone’s respect for privacy regarding this matter.”

Click to Subscribe to Get Our Free HollywoodLife Daily Newsletter to get the hottest celeb news.