Colton Underwood's History of Ups and Downs — from 'Bachelor' Blow-Ups to New Beginnings

A look back at the former Bachelor's tumultuous relationship with ex Cassie Randolph, his coming out journey and his future with Netflix

01 of 16

Big Reveal

Emerald City - Season 1
Paul Hebert/ABC; Noel Vasquez/Getty Images

Former football player Colton Underwood first made waves as a Bachelorette contestant on Becca Kufrin's season in 2018. Underwood found himself in a love triangle between Kufrin and her friend and fellow former Bachelor contestant Tia Booth before confessing on the show that he was a virgin.

Although he had not planned to reveal something that was so personal to him, Underwood said he had no regrets and credited the show for allowing him to "be true to who I am and it allowed me to grow as a person."

"I couldn't be more appreciative of that," he said of his experience on the popular franchise.

02 of 16

Bachelor Debut

Colton Underwood - The BachelorCredit: ABC

In 2019, Underwood hit the ground running as a historic Bachelor.

"I'm the first virgin Bachelor and it's crazy to even think about that," he said during the premiere. "I couldn't be more hopeful and excited."

As the series played out, it got to a pivotal point when it came down to the Fantasy Suites, where Underwood admitted to checking the rooms to make sure no mics or cameras were lingering. During an episode of the LadyGang podcast, Underwood also revealed the worst part about filming his season, saying, "The hardest part is all the virginity talk when I know my grandma's watching."

03 of 16

First Love

Gold Meets Golden - Arrivals
JB Lacroix/WireImage

On the LadyGang podcast, Underwood also opened up about his past relationship with Olympian Aly Raisman. The star, who dated Raisman in 2016, referred to her as his "first love."

"While it was confusing and hard in the beginning, it also taught me a lot about myself — what I need, what I want, what I can do better in a relationship," Underwood said. "It was a big step for me. It was really tough."

04 of 16

Final Rose

Jim Wright

During the two-part finale, Underwood dodged virginity questions from host Chris Harrison and focused on sharing his excitement about a possible future with contestant Cassie Randolph.

As the series unfolded, Underwood broke from tradition by declaring his love for Randolph before the finale — but Randolph did not feel the same way. Audiences were shocked when Randolph suddenly decided to exit the show during their Fantasy Suite date, leaving Underwood heartbroken. In the end, Underwood sent home remaining contestants Tayshia Adams and Hannah Godwin in order to fight for his relationship with Randolph. Once the season aired, the two were thrilled to announce that they were in love.

"We're so excited to be out in public and not have to hide anymore," Underwood told PEOPLE in 2019. "I'm so in love, and I'm ready for everyone to know it."

"We can finally be outwardly happy, and not have to keep this big secret," Randolph added.

05 of 16

A Proposal on Hold

Colton Underwood
Cassie Randolph, Colton Underwood. Jerod Harris/Getty Images

The couple seemed to be going strong as they went on more dates and got to know each others' families. In April 2019, Underwood hinted at an engagement while attending the the 54th Academy of Country Music Awards.

"Honestly, if I was a betting man I would say it would happen within the next year, yes," he told Entertainment Tonight at the time.

06 of 16

Producer Admits to Virginity Overkill

Willy Sanjuan/Invision/AP/REX/Shutterstock.

After a whirlwind season, ABC reality chief Rob Mills admitted that the network went overboard with the discussion around Underwood's virginity.

"Was it too much? Absolutely. But is The Bachelor the poster child for overkill? Absolutely. And I think that's why we love it. It's over-the-top and fun," Mills told The Hollywood Reporter in March 2019.

"Look, we have to own it. We know it's true," he added, speaking about the show's uber-dramatic tendencies. "You saw a lot of people saying a week ago after the fence jump, 'Wow, they said this was the most dramatic thing and for once they were right.' We know there are times where it's obviously not he 'most dramatic' and we hype things up and sometimes over-hype them, but that's kind of the fun of the show."

07 of 16

COVID in Quarantine

Colton Underwood posts update on his coronavirus infection
Colton Underwood/Instagram

In March 2020, Underwood tested positive for COVID-19 and isolated himself at the home of Randolph's parents, where the couple was quarantining together. The star detailed his symptoms on Instagram, explaining that he experienced coughing, night sweats and shortness of breath.

"Breathing is challenging, the best way to describe it is feeling like I only have access to 20% of my lungs," he wrote on Instagram. "I can only imagine how people with pre-existing health conditions feel with this. I've been journaling throughout this and I'll share some of those soon. I'm currently on hydroxychloroquine, Z-Pak and last night the doctor prescribed an inhaler, also. I'm hopeful that they are starting to work!"

08 of 16

Struggling with Sexuality

Colton Underwood Book
Colton Underwood’s The First Time.

In his memoir The First Time, which was released in March 2020, Underwood spoke candidly about being bullied while growing up in the small town of Washington, Illinois. He said he was "called fatso" and "four eyes" and became "super insecure" about himself. Things grew increasingly tough for the star when rumors of him being gay in high school started to circulate.

"It was one of those things where you hear something so often, you start believing it," he said. "I thought, maybe I am gay. The captain of the football team should be having sex and drinking, right? But I wasn't."

His uncertainty about his sexuality wasn't new. Underwood shared that he had searched "Am I gay?" online when he was in grade school.

"I didn't know who I was," he continued. "And I come from an athletic family, so it was always, 'Move on, you're good.' So that threw me off. In high school, when I was struggling with my sexuality, I'm not going to talk to my parents about it. So I internalized it."

09 of 16

Calling It Quits

Colton Underwood, Cassie Randolph
Colton Underwood, Cassie Randolph. Frazer Harrison/Getty

Underwood also revealed in his memoir that he and Randolph had briefly split before getting back together after his season of The Bachelor had aired. The two then officially called it quits in May 2020 following Underwood's battle with COVID. They announced the news on their respective Instagram accounts, and a source told PEOPLE at the time that the breakup was "mutual" and "definitely amicable."

"Colton and Cassie are still good friends, and they want to stay friends. It's definitely a priority for them," the source continued. "Colton is sad, but he's looking forward to what the future may bring."

10 of 16

Messy Aftermath

Cassie Randolph Instagram
Cassie Randolph Instagram

Things took a turn, however, when Randolph called out Underwood for trying to "monetize" their breakup. She addressed the situation in a series of Instagram Stories in July 2020, claiming Underwood had planned to write about their breakup and refused to give Randolph "any sort of approval on the chapter." She concluded her message by writing, "I can't control your actions but I sincerely hope we can both move forward in peace. Thanking you in advance. I would prefer this to now be the end of this. I wish you nothing but the best & hope you can move on peacefully and successfully."

A rep for Underwood told E! News at the time that Randolph's accusations were "simply not true."

11 of 16

New Fling

Colton Underwood; Lucy Hale
Jon Kopaloff/FilmMagic; Amy Sussman/E! Entertainment/NBCU Photo Bank

As Randolph spoke openly on Instagram about how she had been experiencing "an awful few months" since her breakup, Underwood started casually dating actress Lucy Hale.

"They've hung out a few times. They are very casually dating — it's been so complicated to date (in general) during the pandemic," the source told PEOPLE in July 2020, adding that they connected over social media DMs.

12 of 16

Pursing Legal Action

Cassie Randolph Files Restraining Order Against Colton Underwood
Cassie Randolph, Colton Underwood. Amy Sussman/E! Entertainment/NBCU Photo Bank; JC Olivera/WireImage

In September 2020, Randolph filed for a restraining order against Underwood due to alleged harassment and stalking, PEOPLE confirmed. Randolph made numerous claims in the filing, including that Underwood planted a tracking device in her car and sent her concerning text messages. A source told PEOPLE at the time that Randolph felt fearful of Underwood's alleged behavior, prompting her to take legal action.

"After the breakup, Cassie wanted to be friends, and she thought they were on good terms," the source said. "Then the text messages and the frightening behavior started. Cassie was just terrified about how he was acting."

In her filing, Randolph claimed Underwood had "admitted to a few mutual friends and coworkers that he placed the tracker on [her] car and used the alias phone numbers to send the anonymous text messages to [Randolph], himself, and others."

The source said Randolph confronted Underwood about his alleged behavior and then he went out of town.

"When she found out he was coming back in town, she was scared and felt she needed to pursue legal help," the source continued, adding that Randolph harbored no "ill will" but wanted Underwood "to get whatever help he needs."

13 of 16

Chris Harrison Weighs In

Chris Harrison Cassie Randolph Colton Underwood
Chris Harrison, Cassie Randolph and Colton Underwood. Mary Clavering/Young Hollywood/Getty; Slaven Vlasic/Getty

The Bachelor host spoke to Entertainment Tonight about the controversy surrounding the Bachelor alumni in October 2020. He told the outlet that he had reached out to offer his support and hoped that they were "taking care of themselves and each other and being smart about this."

Randolph dropped her restraining order against Underwood in November 2020. In a statement to PEOPLE following the news, Underwood said he and Randolph "were able to reach a private agreement."

"Today Cassie asked the court to dismiss the temporary restraining order against me. The two of us were able to reach a private agreement to address any of Cassie's concerns," he said. "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." (A rep for Randolph did not respond to PEOPLE's request for comment at the time.)

14 of 16

Revealing His Truth

Colton Underwood

After taking a short hiatus from the public eye, Underwood joined Robin Roberts on Good Morning America in an interview that aired on April 14 to announce that he is gay. During the personal conversation, titled "Colton Underwood: In His Own Words," the former Bachelor said he "came to terms" with his sexuality earlier in 2021 after a long period of self-reflection.

"I've ran from myself for a long time. I've hated myself for a long time, and I'm gay. And I came to terms with that earlier this year and have been processing it," Underwood said. "The next step in all of this was letting people know. I'm still nervous. It's been a journey, for sure."

"I'm emotional, but in such a good, happy, positive way," he added. "I'm the happiest and healthiest I've ever been in my life, and that means the world to me."

15 of 16

Saying Sorry

Cassie Randolph, Colton Underwood
Cassie Randolph, Colton Underwood. Paul Archuleta/Getty; Robin L Marshall/Getty

While sitting down with GMA anchor Roberts, Underwood also apologized to Randolph for "how things ended" between them.

"I would like to say sorry for how things ended. I messed up," he said. "I made a lot of bad choices." Underwood went on to say that he had been in love with Randolph, adding, "And that only made it harder and more confusing for me."

"If I'm being very honest, I loved everything about her," he said. "And it's hard for me to articulate exactly what my emotions were going through that relationship with her, because I obviously had an internal fight going on."

He continued, "I would just say I'm sorry from the bottom of my heart. I'm sorry for the pain and emotional stress I caused. I wish it wouldn't have happened the way it did. I wish that I would have been courageous enough to fix myself before I broke anybody else."

16 of 16

New Beginnings

Jim Wright

Underwood will share his coming out journey in an upcoming Netflix reality series, a source confirmed to PEOPLE.

A film crew has been following the former Bachelor star over the last few weeks, according to TMZ. The series will focus on Underwood navigating life as a gay man and will reportedly feature appearances from well-known figures in the LBGTQ community.

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