Inside The Bachelor star Colton Underwood’s bitter split from Cassie Randolph

Former Bachelor star Colton Underwood dropped a bombshell this morning when he came out as gay on Good Morning America, revealing that he spent years hating himself as he struggled with his sexuality and even attempted suicide.

The 29-year-old ex-NFL player also opened up about his relationship with Cassie Randolph, 25, whom he picked as the winner of his 2019 season of the reality romance show.

But while it looked like love for the former couple — with Colton, known as the ‘virgin Bachelor,’ losing his virginity to Cassie — the pair had a dramatic split in 2020, with Cassie later requesting a restraining order against him for allegedly stalking and harassing her with incessant text messages and a GPS tracker on her car.

Speaking to Robin Roberts today, Colton publicly apologized to his ex for how he treated her, explaining: ‘I got into a place with my personal life that was dark, and bad, and I can list a bunch of different things, but they’d all be excuses. I’d like to say sorry for how things ended. I messed up. I made a lot of bad choices.’

Inside the breakup: Bachelor star Colton Underwood and contestant Cassie Randolph went through a dramatic breakup last year

Inside the breakup: Bachelor star Colton Underwood and contestant Cassie Randolph went through a dramatic breakup last year

Inside the breakup: Bachelor star Colton Underwood and contestant Cassie Randolph went through a dramatic breakup last year

Shock announcement: Colton, 29, dropped a bombshell this morning when he came out as gay

Shock announcement: Colton, 29, dropped a bombshell this morning when he came out as gay

 Shock announcement: Colton, 29, dropped a bombshell this morning when he came out as gay

From the heart: He also publicly apologized to his ex for how he treated her, saying: 'I’d like to say sorry for how things ended. I messed up. I made a lot of bad choices'

From the heart: He also publicly apologized to his ex for how he treated her, saying: 'I’d like to say sorry for how things ended. I messed up. I made a lot of bad choices'

From the heart: He also publicly apologized to his ex for how he treated her, saying: ‘I’d like to say sorry for how things ended. I messed up. I made a lot of bad choices’

Lovebirds: After Colton picked Cassie as the winner of season 23, they dated through early 2020, with Colton moving to Los Angeles to be near her

Lovebirds: After Colton picked Cassie as the winner of season 23, they dated through early 2020, with Colton moving to Los Angeles to be near her

Lovebirds: After Colton picked Cassie as the winner of season 23, they dated through early 2020, with Colton moving to Los Angeles to be near her

After playing as a tight end in the NFL from 2014 to 2016, Colton retired and made his first reality TV appearance on The Bachelorette as a contestant in 2018 — where he admitted to Bachelorette Becca Kufrin that he was still a virgin due to his Christian values.

He later appeared on Bachelor in Paradise, and then starred in the 23rd season of The Bachelor in 2018 — where he got to know Cassie, a speech pathologist. 

'I found somebody I wanted to be with,' he told People. 'And I wasn’t willing to give up.'

'I found somebody I wanted to be with,' he told People. 'And I wasn’t willing to give up.'

‘I found somebody I wanted to be with,’ he told People. ‘And I wasn’t willing to give up.’

But their relationship was incredibly tumultuous from the start. After reaching the final three, Cassie broke things off with Colton and left the show, a decision that left Colton so devastated that he jumped over a fence to run after her. 

Colton ultimately picked Cassie as the winner, and though he didn’t propose, the two continued to date, with Colton moving to Los Angeles to be near her.

‘I found somebody I wanted to be with,’ he told People. ‘And I wasn’t willing to give up.’

But even as Cassie helped nurse Colton back to health when he contracted COVID-19 in March of 2020, their relationship wasn’t long for this world.  

In mid-April of 2020, the pair broke up, announcing their split the next month on Instagram.  

‘Its [sic] been a crazy few months to say the least, Cass and I have been doing a lot of self-reflecting,’ Colton wrote.

It's over: In mid-April of 2020, the pair broke up, announcing their split the next month on Instagram

It's over: In mid-April of 2020, the pair broke up, announcing their split the next month on Instagram

It’s over: In mid-April of 2020, the pair broke up, announcing their split the next month on Instagram

'Colton and I have broken up, but have decided to remain a part of each others lives,' Cassie wrote, insisting they were still friends

'Colton and I have broken up, but have decided to remain a part of each others lives,' Cassie wrote, insisting they were still friends

‘Colton and I have broken up, but have decided to remain a part of each others lives,’ Cassie wrote, insisting they were still friends

Reflecting: In July of 2020, Cassie briefly discussed the breakup on The Bachelor: The Greatest Seasons — Ever!

Reflecting: In July of 2020, Cassie briefly discussed the breakup on The Bachelor: The Greatest Seasons — Ever!

Reflecting: In July of 2020, Cassie briefly discussed the breakup on The Bachelor: The Greatest Seasons — Ever!

Angered: After it aired, Colton took to social media to chide Cassie for speaking about their breakup at all

Angered: After it aired, Colton took to social media to chide Cassie for speaking about their breakup at all

Angered: After it aired, Colton took to social media to chide Cassie for speaking about their breakup at all 

‘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.’

Meanwhile, Cassie also wrote that they were staying friends.  

‘Colton and I have broken up, but have decided to remain a part of each others lives,’ she wrote. 

‘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.’

A source told People it was a ‘mutual’ and ‘amicable’ breakup, and they were ‘still good friends,’ while another source later added that in the months following their breakup, they saw each other several times.  

But things weren’t to remain friendly for much longer.  

First, in July of 2020, Cassie briefly discussed the breakup on The Bachelor: The Greatest Seasons — Ever!

‘I think going through any breakup is really hard but going through one in public comes with a whole new set of challenges,’ she said. ‘I mean, I’ve never gone through any of this before so we’re both kind of learning to navigate it. We’re on good terms and hanging in there.’

No you don't! Cassie fired back, accusing her ex of 'subtly engaging in a tactic that peppers in aggressive comments' to make her look like 'the bad one'

No you don't! Cassie fired back, accusing her ex of 'subtly engaging in a tactic that peppers in aggressive comments' to make her look like 'the bad one'

No you don’t! Cassie fired back, accusing her ex of ‘subtly engaging in a tactic that peppers in aggressive comments’ to make her look like ‘the bad one’

Uh-oh: She said Colton said he 'intends to monetize our breakup by writing a new chapter to discuss your experience with COVID,' she said

Uh-oh: She said Colton said he 'intends to monetize our breakup by writing a new chapter to discuss your experience with COVID,' she said

Uh-oh: She said Colton said he ‘intends to monetize our breakup by writing a new chapter to discuss your experience with COVID,’ she said

'This seems a bit unfair to me. Colton, you can do what you want, but please do not have a double standard,' she wrote, asking that they just 'move on peacefully and successfully'

'This seems a bit unfair to me. Colton, you can do what you want, but please do not have a double standard,' she wrote, asking that they just 'move on peacefully and successfully'

‘This seems a bit unfair to me. Colton, you can do what you want, but please do not have a double standard,’ she wrote, asking that they just ‘move on peacefully and successfully’

After it aired, Colton took to social media to chide Cassie for speaking about their breakup at all.

‘When our relationship ended we agreed to handle things as privately as possible as we attempted to navigate our new relationship as friends. I chose to do that since we were living in this interim period, but obviously a lot changed this week,’ he wrote. 

Cassie then fired back on Instagram, writing: ‘I would like to state that I do not wish to create an online petty war. Colton, as you know we made an agreement to not publicly discuss our break up. I have honored this, as have you thus far.

‘I didn’t see any harm in doing the interview, as I wasn’t going to dish out details about our relationship to them,’ she went on, saying Colton’s post ‘saddened’ and ‘frustrated’ her.

She accused her ex of ‘subtly engaging in a tactic that peppers in aggressive comments’ to make her look like ‘the bad one.’

‘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.

‘On Monday evening [July 6], 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) & about our breakup,’ she went on.

‘This seems a bit unfair to me. Colton, you can do what you want, but please do not have a double standard,’ she wrote, asking that they just ‘move on peacefully and successfully.’ 

Scared: Then, on September 11, 2020, the split took a dramatic turn when Cassie filed a request for a restraining order with the Superior Court of California

Scared: Then, on September 11, 2020, the split took a dramatic turn when Cassie filed a request for a restraining order with the Superior Court of California

Scared: Then, on September 11, 2020, the split took a dramatic turn when Cassie filed a request for a restraining order with the Superior Court of California

Creepy: She accused Colton of stalking her and harassing her and was granted a temporary restraining order

Creepy: She accused Colton of stalking her and harassing her and was granted a temporary restraining order

Creepy: She accused Colton of stalking her and harassing her and was granted a temporary restraining order

Evidence: She shared several screenshots of the numerous text messages he would send her

Evidence: She shared several screenshots of the numerous text messages he would send her

Evidence: She shared several screenshots of the numerous text messages he would send her

Messages: He also sent messages to Cassie's friends, and knew when a male friend had come to her home

Messages: He also sent messages to Cassie's friends, and knew when a male friend had come to her home

Messages: He also sent messages to Cassie’s friends, and knew when a male friend had come to her home

Then, on September 11, 2020, the split took a dramatic turn when Cassie filed a request for a restraining order with the Superior Court of California, County of Los Angeles. In the request, Cassie asked that Colton be legally barred from approaching her, her home, her workplace, her school, her car, or even her parents.

In documents filed with the request to the court and obtained by DailyMail.com, Cassie cited abuse that allegedly occurred in ‘various incidents since June 2020.’

The documents allege that Colton was ‘stalking and harassing’ her, sending her ‘unsettling text messages,’ repeatedly calling her, and placing ‘a tracking device on her vehicle to track her whereabouts’.

The restraining order request also said that Colton had been seen outside her parents’ home in Huntington Beach, California, on several occasions, including one time he was outside Cassie’s bedroom window at two in the morning. 

‘Mr. Underwood also watches Ms. Randolph’s apartment in Los Angeles. Mr. Underwood admitted to his roommate and his roommate’s girlfriend (who is also Ms. Randolph’s friend) that he goes on multiple walks a day to Ms. Randolph’s apartment building,’ the document continued. 

Colton ‘obsessively called and sent text messages’ when Cassie had a male visitor, leaving Cassie ‘startled that he knew who was coming in and out of her apartment, and felt like she was being watched.’ 

He sent similar messages when she visited her family and friends, indicating that he knew where she was, the documents read. 

Obsessed: Cassie accused him of sending incessant messages to her friends and family

Obsessed: Cassie accused him of sending incessant messages to her friends and family

Obsessed: Cassie accused him of sending incessant messages to her friends and family

She even started getting harassing messages from unknown numbers, which Colton later admitted he was sending

She even started getting harassing messages from unknown numbers, which Colton later admitted he was sending

She even started getting harassing messages from unknown numbers, which Colton later admitted he was sending

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More evidence: She submitted several screenshots of the messages from fake numbers

More evidence: She submitted several screenshots of the messages from fake numbers

More evidence: She submitted several screenshots of the messages from fake numbers

Attention: What's more, he allegedly used those same fake numbers to send harassing messages to his own phone number

Attention: What's more, he allegedly used those same fake numbers to send harassing messages to his own phone number

Attention: What’s more, he allegedly used those same fake numbers to send harassing messages to his own phone number

In addition to sending her frequent text messages from his own number — and also texting members of her family — Colton also allegedly ‘used alias phone numbers to anonymously send harassing text messages at all hours of the day to Ms. Randolph and to her friends.’ 

What’s more, he allegedly used those same fake numbers to send harassing messages to his own phone number.

Suspicious that Colton might be tracking her car, Cassie and her family investigated on August 19 and found a ’tile tracking device taped to the bottom of the back bumper of her car.’  

Two days later, Cassie confronted Colton and told him she called the police and hired a private investigator over the car tracking, according to the documents.

‘Mr. Underwood admitted that he was the one who put the tracker on her car and had been the one sending text messages to her, her friends and himself, under the alias phone numbers described above,’ the restraining order request reads.

He also reportedly admitted as much to mutual friends.

Cassie filed for the restraining order due to ‘fears for her safety and the safety of her family and friends and wants to ensure that the harassment and stalking behavior cease when he returns to Los Angeles [from a trip to Denver].’

Several screenshots of text messages, as well as photos of the car tracker, were included in the report.   

Following: Cassie and her family investigated on August 19 and found a 'tile tracking device taped to the bottom of the back bumper of her car'

Following: Cassie and her family investigated on August 19 and found a 'tile tracking device taped to the bottom of the back bumper of her car'

Following: Cassie and her family investigated on August 19 and found a ’tile tracking device taped to the bottom of the back bumper of her car’

It's him: Two days later, Cassie confronted Colton, and claimed he admitted that he had placed the device there

It's him: Two days later, Cassie confronted Colton, and claimed he admitted that he had placed the device there

It’s him: Two days later, Cassie confronted Colton, and claimed he admitted that he had placed the device there

Cassie was ultimately granted a temporary restraining order that forced Underwood to stay at least 100 yards away from her, in addition to her car, home, workplace, and school. 

Later, however, Cassie dismissed the restraining order against Colton, and requested to drop the police investigation.

‘Today Cassie asked the court to dismiss the temporary restraining order against me, Colton reportedly told TMZ on November 3. 

‘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. I appreciate everyone’s respect for privacy regarding this matter.’ 

Now, Colton has finally copped to bad behavior in his new GMA interview. 

In addition to saying he ‘messed up’ and ‘made a lot of bad choices’ while apologizing ‘for how things ended,’ he also said he was sorry for continuing a relationship with her even though he is gay, admitting he was still struggling with how to come to terms with his sexuality. 

‘Yes [I was in love with her],’ he insisted. ‘It… made it harder and more confusing for me, if I’m being honest. I loved everything about her and it’s hard for me to articulate exactly what my emotions were in going through that relationship with her was, because I obviously had an internal fight going on.

Moving on: Later, however, Cassie dismissed the restraining order against Colton, and requested to drop the police investigation

Moving on: Later, however, Cassie dismissed the restraining order against Colton, and requested to drop the police investigation

Moving on: Later, however, Cassie dismissed the restraining order against Colton, and requested to drop the police investigation

‘I would just say that I’m sorry from the bottom of my heart. I’m sorry for any 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.’ 

Colton’s emotional interview this morning also revealed details of his ongoing struggles. 

‘Obviously this year’s been a lot for a lot of people and it’s probably made a lot of people look themselves in the mirror and figure out who they are and what they’ve been running from or putting off in their lives, and for me, I’ve ran from myself for a long time,’ he explained. ‘I’ve hated myself for a long time.’

When asked whether he ever attempted to harm himself, Colton admitted that there was a ‘moment in LA’ when he tried to take his own life.

‘There was a moment in LA [when] I woke up and I didn’t think I was going to wake up,’ he revealed. ‘I didn’t have the intentions of waking up and I did.’

Colton said he had thought that being chosen for The Bachelor was a sign that God was ‘making him straight’.

‘I literally remember praying to God the morning I found out that I was a Bachelor and thanking him for making me straight,’ he recalled.

‘I remember that vividly, saying, like, “Finally you’re letting me be straight. Finally you’re giving me a wife, a fiancee and then I’m going to have the kids then I’m going to have the house and have all this.”‘ 

Bombshell: Colton's emotional interview this morning also revealed details of his ongoing struggles

Bombshell: Colton's emotional interview this morning also revealed details of his ongoing struggles

Bombshell: Colton’s emotional interview this morning also revealed details of his ongoing struggles

Struggle: Colton admitted that his struggle with his sexuality drove him to attempt suicide, explaining that there was a 'moment in LA... [when he] didn't have the intentions of waking up'

Struggle: Colton admitted that his struggle with his sexuality drove him to attempt suicide, explaining that there was a 'moment in LA... [when he] didn't have the intentions of waking up'

Struggle: Colton admitted that his struggle with his sexuality drove him to attempt suicide, explaining that there was a ‘moment in LA… [when he] didn’t have the intentions of waking up’

Denied: In his memoir, Colton had recalled the time his father found out that he had looked at gay porn

Denied: In his memoir, Colton had recalled the time his father found out that he had looked at gay porn

Denied: In his memoir, Colton had recalled the time his father found out that he had looked at gay porn

Speaking candidly, he opened up about how his Catholic upbringing made him suppress his sexuality for years, admitting that he has ‘known he was different since the age of six’ and realized he was gay when he was a freshman in high school — but felt he had to suppress his sexuality because he’d always been taught it was ‘a sin.’

‘I was a freshman in high school when I knew I was gay and by that time I had already grown up in the Catholic church, I [had] gone to Catholic grade school, [and] I had learned in the Bible that [being] gay is a sin,’ he said, adding that he was always made to feel that being gay was bad because the label was used to criticize things by many of his football teammates growing up.

‘I had made mistakes in my sports and my athletic career and when you make mistakes, that play was gay or gay was always affiliated with a connotation of negativity and I think there’s a lot of things when I look back I’m like no wonder I held it in,’ he shared.

In his memoir, Colton had recalled the time his father found out that he had looked at gay porn. 

‘He’d pulled up the history of recent Google searches, which included gay porn sites and a variety of questions: Am I gay? How do you know if you’re gay? Why don’t I like having sex with my girlfriend?’ he wrote.

‘At first, I denied responsibility. Then I owned up to having been curious. He asked if I wanted to talk about it. I said no, explaining that I’d figured things out on my own. I begged him not to tell Mom. I’m sure he did. But neither of them ever spoke about it with me. All that research, though, led me to understand that I was definitely attracted to girls.’

Love: Colton said that his father Scott was incredibly supportive when he came out, revealing his dad asked him, 'How can I help you? How can I help fake this off your plate? Who can I tell?'

Love: Colton said that his father Scott was incredibly supportive when he came out, revealing his dad asked him, 'How can I help you? How can I help fake this off your plate? Who can I tell?'

Love: Colton said that his father Scott was incredibly supportive when he came out, revealing his dad asked him, ‘How can I help you? How can I help fake this off your plate? Who can I tell?’

Emotional: The Bachelor star (pictured with his mom Donna) added that many of his closest friends and family said they wish he had felt he could come out to them sooner

Emotional: The Bachelor star (pictured with his mom Donna) added that many of his closest friends and family said they wish he had felt he could come out to them sooner

Emotional: The Bachelor star (pictured with his mom Donna) added that many of his closest friends and family said they wish he had felt he could come out to them sooner

Colton added in his new interview that he is now the ‘happiest and healthiest’ he has ever been after fully embracing his sexuality, admitting that it was something he ‘never thought he was going to share’.

He told GMA that he is yet to have an ’emotional connection with a man’ and said it hasn’t yet been ‘in my cards to let myself get there’ with a man. But he added: ‘I want to more than anything’.

Last year, Cassie was rumored to be dating singer Brighton Randolph, but he later denied the claim, saying they were ‘just friends and have been for over four or so years’.

Colton also issued an apology to the women that he dated and ‘misled’ during his time on The Bachelor franchise, as well as the viewers who – as Roberts noted – ‘were cheering him on and wanting him to find love’.

‘I just wish I wouldn’t have dragged people into my own mess of figuring out who I was,’ Colton admitted.

‘I genuinely mean that. But I also at the same time like but I can sit here and say I’m sorry to all those women and can also say thank you because without them and without the bachelor franchise, I don’t know if like this would have ever came out.’  

The former Bachelor said that he has privately come out to his closest friends and family, and has received a wealth of ‘love and support,’ although he did not reveal whether he had spoken to his ex-girlfriends personally about his sexuality before appearing on GMA.

‘I’ve had sort of a range of responses and the underlining most common one was almost like, “I wish you would have told me sooner,”‘ he revealed.

‘When I hear that, I wish I would have had faith in my friends and family a little more. My dad, I told him and his reaction was sort of the same: “I wish you would have trusted me sooner,” but then he followed it up with, “How can I help you? How can I help take this off your plate? Who can I tell?”

‘That was more meaningful than I love you. The only reason I’m sitting down is because I have the love and support of my friends and family.’ 

Colton Underwood’s relationship history and time on The Bachelor

Olympic gymnast Aly Raisman (August 2016-April 2017)

Colton asked Aly out on a date via a pre-recorded video while she was filming a Yahoo! Sports segment about what she was looking for in a boyfriend.

In the video, Colton praised Aly’s Olympic success, before telling her that if she is ‘ever in San Jose,’ he would love to take her out on a double date. 

Aly followed up with the sports star on Twitter, thanking him for the video and saying she was ‘looking forward to meeting him.’

Soon after, the couple began dating, and attended several high-profile events together, including a Golden Globes after party in January 2017. 

In his book, The First Time, Colton revealed that he told Aly he was a virgin during their second date, and said that they both agreed to take things slowly. She later opened up about the sexual abuse she suffered at the hands of pedophile doctor Larry Nassar, with the NFL player admitting that he wanted to ‘find Nassar and rip his head off’ after she shared the trauma he had put her through.  

However, their relationship came to an abrupt end in April of that same year, with Colton later revealing that the gymnast left him broken hearted after ending their romance via FaceTime. 

‘I pulled over to the side of the road, stunned an unable to comprehend this was happening,’ he revealed. ‘Aly said she felt overwhelmed, confused and in need of a break. Afterward, I sat in my car and cried. I was numb for days.’ 

He later admitted that the split was his ‘worst heartbreak’ while describing Aly has his ‘first love.’ 

The Bachelorette – Becca Kufrin (2018)

Colton made his debut on ABC’s Bachelor franchise as a contestant on the 14th season of The Bachelorette, during which he attempted to capture the heart of star Becca Kufrin. 

During the show, Colton revealed to Becca that he was still a virgin, explaining that he had dedicated so much time to his football career that he ‘sort of forgot who personal Colton was… and because of that he was still a virgin.’

The former NFL player admitted during that episode, which aired in July 2018, that he had been afraid the admission would be a ‘deal breaker’ for her. But while she seemed stunned by the confession, Becca later gave Colton a rose and he proceeded through to the next week.

He made it to the final four men, before Becca sent him home in the eighth week of the show after discovering that he still had feelings for her close friend Tia Booth, whom he had dated before appearing on The Bachelorette.

The Bachelor in Paradise (2018)

After being sent home from The Bachelor, Colton went on to land a spot as a contestant on the fifth season of spin-off show Bachelor in Paradise, during which he rekindled his romance with ex Tia for just a few weeks.    

Tia had appeared alongside Becca as a contestant in Arie Luyendyk Jr.’s season of The Bachelor, and when it was announced that she would be appearing on the Paradise spin-off, many viewers quickly speculated that she and Colton would begin dating again. 

As predicted, Colton and Tia quickly formed a close bond, and the football player soon asked his ex flame to be his girlfriend. 

However, he left her broken hearted when he ended their relationship just a few weeks later, admitting that he wasn’t ready to commit. 

In his book, Colton insisted that he had never wanted to pursue Tia on the show, claiming that producers had pushed him into the romance, telling him that if he struck up a relationship with her on Bachelor in Paradise, he would have a better shot at being chosen as the next Bachelor. 

He said that he ended his relationship with Tia on the spin-off because he felt such immense guilt about stringing her along. 

The Bachelor (2019)

Colton was announced as the star of season 23 of The Bachelor, and was quickly labeled ‘the virgin Bachelor’ thanks to his admission that he had never had a sex. 

His virginity was a major focus for the majority of the season, with many questioning whether he would choose to have sex with one of the women on the show while filming was taking place.  

In addition to the speculation about his sex life, Colton’s debut as The Bachelor quickly became embroiled in controversy when an early teaser clip revealed that he had seemingly quit mid-way through filming. 

The footage, which was shown in the premiere episode, showed Colton jumping over a fence and running away from the cameras in a shock twist that left viewers stunned.   

During the episodes that led up to that controversial moment, Colton was seen forming a close relationship with contestant Cassie Randolph, who made it through to the final week, during which she and the other remaining woman — Tayshia Adams — had the chance to spend the night with the NFL player. 

Many believed that Colton planned to lose his virginity to Cassie during their overnight date, however, she shocked viewers by breaking up with him when he revealed that her father had refused to give their relationship his blessing when the couple visited Cassie’s hometown.  

Her decision left Colton devastated, and he was seen begging her to stay — even telling Cassie that he would be happy to continue their relationship without an engagement. After she declined, Colton lashed out at the cameras, and fled production, leaping over a fence and running off into the night. 

In the follow-up episode, Colton revealed that he had confessed his love to Cassie, who eventually agreed to give the relationship a go — without a proposal. 

Colton later hinted in his book that he had lost his virginity to Cassie during filming.  

The couple dated from November 2018 until May 2020, when they split — with Cassie, 25, later filing a restraining order against her ex, accusing him of stalking her and putting a tracking device on her car.  

She was granted a temporary restraining order that forced Underwood to stay at least 100 yards away from her, in addition to her car, home, workplace, and school.

Cassie accused Colton of harassing her with text messages and showing up at her home uninvited. She also claimed he would loiter outside her parents house in Huntington Beach, California in the early hours of the morning. 

Later, Cassie dismissed the restraining order against Colton, and requested to drop the police investigation.  

‘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. I appreciate everyone’s respect for privacy regarding this matter,’ Colton said. 

Lucy Hale (2020) 

In July last year, Colton was spotted enjoying a hike with Pretty Little Liars star Lucy in Los Angeles, and rumors quickly spread that the couple were dating. 

A source told People at the time that the pair had ‘hung out a few times’ and were enjoying a ‘casual’ romance, however, the reports were never confirmed, and just one day after Colton and Lucy were seen hiking together, she told Entertainment Tonight that she was still single.  

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