Messiest Bachelor Nation Breakups (original) (raw)

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Not all Bachelor Nation breakups are as pretty as a rose.

Colton Underwood and his Bachelor season 23 winner Cassie Randolph, for example, vowed to stay friends when they went public with their split in May 2020. Things quickly turned sour after Colton shaded Cassie’s decision to do an interview with Chris Harrison during the summer of 2020, where she accused him of profiting off their breakup by adding a chapter about their breakup to his book, The First Time.

Colton later claimed in August 2020 that the exes buried the hatchet — and Cassie agreed to help him with the chapter.

“I wrote the chapter and she saw it and was OK with it and we made changes. I say we. I know it’s my book but like, there was more than just the breakup that was going to go into the book, the extra chapter,” he said on Reality Steve’s podcast at the time. “The chapter is part our breakup and part me having COVID. We go into the details that we’re comfortable sharing in that chapter and we both went over it together. … Honestly, I think her being a part of it made it even better.”

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Cassie was granted a temporary restraining order against Colton in September 2020, citing that she was “fearful for her safety.” The order against Colton — who later came out as gay — was dropped that November.

Scroll through for a breakdown of the messiest breakups in Bachelor Nation:

Credit: Marion Curtis/Starpix/Shutterstock; Danny Moloshok/Invision/AP/Shutterstock

The Messiest Bachelor Nation Breakups of All Time: From Andi and Josh to Colton and Cassie and More

Not all Bachelor Nation breakups are as pretty as a rose.Colton Underwood and his Bachelor season 23 winner Cassie Randolph, for example, vowed to stay friends when they went public with their split in May 2020. Things quickly turned sour after Colton shaded Cassie’s decision to do an interview with Chris Harrison during the summer of 2020, where she accused him of profiting off their breakup by adding a chapter about their breakup to his book, The First Time. Colton later claimed in August 2020 that the exes buried the hatchet — and Cassie agreed to help him with the chapter. “I wrote the chapter and she saw it and was OK with it and we made changes. I say we. I know it’s my book but like, there was more than just the breakup that was going to go into the book, the extra chapter,” he said on Reality Steve’s podcast at the time. “The chapter is part our breakup and part me having COVID. We go into the details that we’re comfortable sharing in that chapter and we both went over it together. … Honestly, I think her being a part of it made it even better.” Cassie was granted a temporary restraining order against Colton in September 2020, citing that she was “fearful for her safety.” The order against Colton — who later came out as gay — was dropped that November. Scroll through for a breakdown of the messiest breakups in Bachelor Nation:

Credit: Marion Curtis/Starpix/Shutterstock; Danny Moloshok/Invision/AP/Shutterstock

The Messiest Bachelor Nation Breakups of All Time: From Andi and Josh to Colton and Cassie and More

Not all Bachelor Nation breakups are as pretty as a rose.Colton Underwood and his Bachelor season 23 winner Cassie Randolph, for example, vowed to stay friends when they went public with their split in May 2020. Things quickly turned sour after Colton shaded Cassie’s decision to do an interview with Chris Harrison during the summer of 2020, where she accused him of profiting off their breakup by adding a chapter about their breakup to his book, The First Time. Colton later claimed in August 2020 that the exes buried the hatchet — and Cassie agreed to help him with the chapter. “I wrote the chapter and she saw it and was OK with it and we made changes. I say we. I know it’s my book but like, there was more than just the breakup that was going to go into the book, the extra chapter,” he said on Reality Steve’s podcast at the time. “The chapter is part our breakup and part me having COVID. We go into the details that we’re comfortable sharing in that chapter and we both went over it together. … Honestly, I think her being a part of it made it even better.” Cassie was granted a temporary restraining order against Colton in September 2020, citing that she was “fearful for her safety.” The order against Colton — who later came out as gay — was dropped that November. Scroll through for a breakdown of the messiest breakups in Bachelor Nation:

Credit: Craig Sjodin/ABC

Matt James and Rachael Kirkconnell

After opting not to propose, the season 25 Bachelor pulled the plug on their relationship while the show was still airing after Kirkconnell made headlines for her past racially insensitive actions. During the March 2021 After the Final Rose, the Georgia native said she was “blindsided” by his decision, which came after her apology for attending an "Old South"-themed party. One month later, the twosome were seen walking together in New York City.

While a source told Us in April 2021 that Matt “was not looking for a romantic relationship with Rachael and was just trying to “support” her after the show, a second insider claimed they were “working on their relationship privately over the past few months and taking the next steps to get back together.”

The second source added that Rachael was “very emotional” after learning Matt was “talking to another girl” during the trip.

The twosome proved to be stronger than the drama in May 2021, confirming they were giving things another shot.

Credit: Courtesy Kelley Flanagan/Instagram

Peter Weber and Kelley Flanagan

The Bachelor season 24 couple met right before filming began in the fall of 2019. On the show, Kelley was sent packing ahead of hometowns, while Peter proposed to Hannah Ann Sluss. Peter and Hannah later called off their engagement and the pilot briefly pursued a relationship with his runner-up, Madison Prewett. In March 2020, however, he started dating Kelley. Us confirmed the following month that the couple were officially dating.

The California native announced their split eight months later on New Year’s Eve. The lawyer confirmed that the pair briefly got back together before calling it quits for good in February 2021. Kelley then detailed the alleged reasons behind their final split during a May 2021 appearance on the “Chicks in the Office” podcast, claiming that their difference in hobbies played a part in the relationship’s end.

“It’s not a bad thing, [but] he loves Pokémon cards and he loves playing video games and he loves going out and partying,” she said at the time. “There was a while where I was trying to convince myself that that’s what I liked and I was like, ‘Alright, Kelley, let’s be honest with yourself. Does that add up for you?’”

The Illinois native claimed that following a “great” Valentine’s Day reunion in New York City things blew up. “It ended really badly,” she said, explaining she left NYC to go to a friend’s house. “He texted me, I didn’t respond and then found some news out that I wasn’t happy about. We still had each other on Find My Friends. … I went off and essentially said, like, ’Get the hell out of my life.’ It ended really badly.”

Peter spoke out about his ex’s comments days later on his “Bachelors in the City” podcast, saying, “I’m just going to be so brutally honest with you guys for however long this goes on for and just speak from the heart — I thought it was very calculated. I thought after hearing how it went that it was very — trying to push for a headline.”

He noted that it felt “very disingenuous” and that it wasn’t something he “expected” from Kelley. “It kind of caught me off guard,” Peter added.

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Clare Crawley and Dale Moss

The Bachelorette season 16 couple’s whirlwind romance — Clare ended her relationships with the other men within the first two weeks of filming to be with Dale — came crashing down in January 2021. Following a five-month engagement, Us confirmed that Clare and Dale were on the rocks. While the athlete subsequently confirmed they had split, the hairstylist later alleged that he announced the breakup without her knowledge.

“I was made aware of a ‘mutual’ statement at the same time you all were, so I’ve needed some time to really digest this,” Clare wrote via Instagram. “Speaking for myself, my intentions with this relationship have always been very clear, so the truth is I am crushed. This was not what I expected or hoped for and am still trying to process this.”

Clare added that their relationship wasn’t “perfect,” but she was “genuinely invested with all of [her] heart.” Two days earlier, Dale wrote that their split was “the healthiest decision” for both of them.

“We appreciate the love and support we’ve received from so many people,” he wrote. “We strongly believe in leading with love and always remaining true to oneself — something our families have taught and instilled in us throughout our lives. We only hope the best things for one another.”

In February 2021, Clare and Dale sparked speculation that they were back on after they were spotted together in Florida. Us broke the news that month that they were back on.

Credit: Marion Curtis/Starpix/Shutterstock

Andi Dorfman and Josh Murray

The season 10 Bachelorette detailed her tumultuous split from her fiancé in her first book, It’s Not Okay, calling their relationship the “most volatile and f–ked up” of her life. After the tell-all was released in 2016, Josh denied Andi’s accusations that he was emotionally abusive.

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Jake Pavelka and Vienna Girardi

The season 14 Bachelor couple blamed their issues on each other during an explosive interview with Harrison in 2010. "I'm disgusted with you," Jake told the emotional Vienna at the time. "What guy in America would ever want to be intimate with someone who undermines him, emasculates and doesn't respect him?"

Credit: Matt Klitscher/ABC

Jason Mesnick and Melissa Rycroft

Jason made history in 2009 as the first Bachelor who changed his mind after the season 13 finale, breaking up with Melissa to pursue runner-up Molly Malaney. (Jason and Molly wed in 2010 and share daughter Riley.)

“I was so angry with the whole production. I was like, ‘They all lied to me. They all got me here. They got me dressed up.’ [And] I was furious with him for doing it to me,” Melissa recalled to Us in 2020. “[But] I’m like, ‘Listen, we are so OK, and we are right where we’re supposed to be. If Jason and I got married, it would have been the biggest blowup ever, like, it would have been terrible. We are not supposed to be together.”

Credit: Tony DiMaio/Startraks

Marcus Grodd and Lacy Faddoul

The season 1 Bachelor in Paradise couple may have walked down the aisle in Mexico, but it turned out that they never legally wed. After news of their split broke in 2016, Marcus publicly slammed Lacy. “I definitely feel played,” he told Us at the time, claiming things “progressively changed on her side.”

Credit: Courtesy of Robby Hayes/Instagram

Amanda Stanton and Robby Hayes

Following a fling on season 4 of BiP, photos of Robby making out with another girl surfaced online.

“When a fan direct messaged me a photo of Robby kissing another girl at a concert, I was further convinced he wasn’t truly interested in any type of relationship or commitment. … I felt his motivation was to look good and get more airtime,” she wrote in her 2019 book, Not Accepting Roses.

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Amanda Stanton and Josh Murray

Much like his relationship with Andi, Amanda’s engagement to Josh also ended with a tell-all book and accusations that he was controlling.

“I would even have to wait for him to go to the gym so I could call my best friend Lauren Bushnell. Or even my mom! He didn’t approve of my childhood friends or my neighbors,” Amanda wrote. “When I caught him peaking beneath the bathroom door to make sure I wasn’t texting anyone, I finally had enough from this experience.”

Josh never publicly commented on Amanda’s memoir.

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Arie Luyendyk Jr. and Becca Kufrin

A decade after Jason’s finale switch-up, Arie broke off his engagement to Becca during the season 22 finale because he wasn’t over runner-up Lauren Burnham. After ABC aired their entire breakup unedited in March 2018, Minnesota State Representative Drew Christensen proposed a bill to ban Arie from Becca’s home state. In the end, Arie married Lauren, welcoming daughter Alessi in 2019, and Becca was named the Bachelorette. While she got engaged to Garrett Yrigoyen during the 2018 finale, they split in 2020.

Credit: Courtesy of Jenna Cooper/Instagram; Courtesy of Jordan Kimball/Instagram

Jenna Cooper and Jordan Kimball

After getting engaged on season 5 of BiP, Jenna was accused of having a “sugar daddy” and lying to Jordan about her intentions when her alleged text messages were published online. Reality Steve, who posted the alleged texts, later apologized. Nearly two years after the scandal — and their split — Jenna opened up to Us about Bachelor Nation turning against her.

“I thought that Jordan would defend me and we would get through it together, but it turned out very different. I mean it was a big downward spiral,” she said. “I know what happened initially and how bullied I was, and part of me just never wanted to talk about it, but I couldn’t let it go and it feels amazing. I can’t even describe it. It feels great to get the truth out.”

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Hannah Ann Sluss and Peter Weber

A third switcheroo went down in 2020 when Peter broke off his engagement to Hannah Ann because he was still thinking about runner-up Madison Prewett while season 24 of The Bachelor was airing. “Word of advice, if you want to be with a woman, you need to become a real man,” Hannah Ann quipped during their heated After the Final Rose confrontation.

After Peter and Madison went their separate ways for good, Peter reunited with Kelley Flanagan, who came in fifth place on the series.

Credit: Broadimage/Shutterstock

Courtney Robertson and Ben Flajnik

She made headlines for being the “villain” of the show, but the season 16 Bachelor was accused of cheating on his new fiancée in 2012. Despite the rocky start, Courtney and Ben were engaged for 10 months before going their separate ways. After she detailed their breakup in her 2014 book, I Didn’t Come Here to Make Friends, he publicly slammed her.

Credit: Peter Brooker/Shutterstoc

Byron Velvick and Mary Delgado

Mary, who was Byron’s final pick on season 6 of The Bachelor, was arrested in 2007 following an altercation between the two of them.

"Just because you met on a reality show, got engaged on this beautiful incredible setting doesn't mean that we're Prince Charming or Beautiful Princess," Byron said in a statement after Mary’s 2007 arrest. ”It's nothing like that. It's just a real couple going through real things."

Bryon and Mary split for good in 2009.

Credit: Danny Moloshok/Invision/AP/Shutterstock

Cassie Randolph and Colton Underwood

Per Cassie’s restraining order, she claimed that Colton was harassing her with “unsettling text messages,” allegedly placed “a tracking device on her vehicle” and would show up to her home uninvited. Colton was ordered to stay 100 yards away from his ex.

After the details of the restraining order were made public, a rep for Colton told Us, “As this is a legal matter, we cannot provide any comment at this time.”

Colton broke his silence on November 3, 2020, claiming Cassie dropped the investigation and order.

“Today Cassie asked the court to dismiss the temporary restraining order against me,” he told Us in a statement. “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 came out as gay in 2021 and went on to wed Jordan C. Brown in 2023. Cassie, for her part, celebrated her fourth anniversary with boyfriend Brighton Reinhardt (a.k.a. Brighton Taylor), in August 2024.

Credit: ABC/Craig Sjodin

Rachel Recchia and Tino Franco

Shortly after Rachel and Tino got engaged on The Bachelorette season 19 finale in September 2022, it was revealed that the pair had broken up post-filming as a result of Tino kissing a woman he had met before joining the show. Fans watched their filmed breakup play out on the After the Final Rose special, during which Tino expressed regret for his actions.

However, he seemingly shaded Rachel for joining the season 9 cast of Bachelor in Paradise in August 2023. “I’ll be watching, but focusing my rooting on for the boys,” he said on the “After Reality podcast.

Rachel clapped back during an interview on “The Viall Files” podcast one month later, questioning, “Why am I not allowed to move on? And why am I not allowed to find love?”

She also alleged that there was “so much more” between Tino and the woman he cheated with than just a kiss, and that he had planned on “seeing” the girl before being cast on The Bachelorette. “There was this emotional relationship happening and this person that it happened with was someone he was going to date after the show,” Rachel claimed. “It’s just hard for me to hear him continue to say ‘Oh it was just this one drunken mistake,’ because it wasn’t.”

Rachel continued: “I guess there’s just a lot to the story. It doesn’t matter now, I really have moved forward. That’s not something I want to harp on or be like ‘He was wrong for this, this and this.’ I guess it’s just hard to know what I know and still have this coming out.”

Credit: DISNEY/John Fleenor

Jenn Tran and Devin Strader

Like many Bachelor Nation couples before them, Jenn and Devin broke up after filming and getting engaged on season 21 of The Bachelorette. During the show’s September 2024 After the Final Rose, Jenn claimed that Devin began “pulling away” from her after the show and eventually confessed that he was no longer in love with her. Their Hawaii proposal was still aired despite their split, something Jenn exclusively told Us she “wanted” Devin to watch.

During AFR, Jenn revealed that Devin had followed her former Bachelor season 28 castmate Maria Georgas, who turned down the offer to be the season’s leading lady before Jenn was cast, the morning after their breakup. Maria clarified in a TikTok video that she had never met Devin and that he unfollowed her by time the follow was brought to her attention.

Devin shared his side of events in a lengthy Instagram video not long after, claiming that he wasn’t Jenn’s “first choice,” referring to her runner-up Marcus Shoberg. He noted that watching Jenn and Marcus’ feeling play out on the small screen only “reaffirmed” his decision to call it quits.

In addition to sharing texts between him and Jenn — which he quickly deleted and apologized for sharing — to back his defense, he took “full accountability” for following Maria in another lengthy Instagram video.

“I shouldn’t be following people that I have no relationship with whatsoever. I don't know Maria, I've never met Maria, I’ve never met up with Maria, and I will never follow Maria,” he stated. “I know I hurt Jen now … I’m just here to apologize for that, so I am sorry.”

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