Bachelorette Dates That Almost Ruined The Whole Season

Usually, a single date can only be so bad. But on "The Bachelorette," a rough date can seem way more devastating. The long-running reality TV series — known for its headline-making scandals and the fact not all of the couples end up staying together — is basically love and dating on steroids, so it's perhaps not too surprising that some of the worst dates in the show's history have been, well, pretty epic. When these particular onscreen dates go down, they can end in tears, total meltdowns complete with lots of screaming, and, of course, tabloid hearsay. 

Whether the dates are devastating, drama-filled, or just so awkward it's not clear if anyone involved could ever recover, a handful of "Bachelorette" dates have been so rough, they've seemed capable of derailing the entire season in which they appeared. From guys who revealed in truly awful ways that they were, in fact, there for the most wrong of wrong reasons, to group date disasters and woefully-bad hometown meet-cutes the fam, here are some of the worst dates on "The Bachelorette" ever that almost ruined the whole season.

When Ashley Hebert led Season 7 of "The Bachelorette" in 2011, she was already plagued by insecurities that the male contestants were let down when the likes of fellow "Bachelor" alumni like Emily Maynard and Chantal O'Brien weren't named that season's bachelorette, per OK! magazine. Unfortunately, things took a turn from not great to outright bad when Ashley went on a group date in which 10 of the men were tasked with roasting her. The event was hosted by Jeffrey Ross, ​​Comedy Central's own Roast Master General, and Will Holman — an aspiring comedian — saw it as an opportunity to advance his career.

"I really want to make Ashley laugh, but I may make her cry tonight," Will told the cameras when he learned the date was a roast (via OK!). "It's ruthless. An opportunity to finally be real with Ashley. I'm gonna be real." While most of the guys decided to mostly joke about the other contestants or poke fun at things like Ashley's flat chest (sigh), Will's routine was much harsher. "Ashley: so beautiful, so gorgeous, so used. They say one man's trash is another man's treasure. I thought I signed up to be with Emily or Chantal and then Ashley's here," he said, touching on a sore subject. "Get out your cell phones to donate to the Ashley boob fund." 

With Ashley left in tears, Will finally read the room and ultimately bowed out of the rest of the evening, per Entertainment Weekly.

Before she was promoted to co-host of the series, Kaitlyn Bristowe spent time looking for love in 2015 as the lead of "The Bachelorette" during Season 11. Usually, the odd group dates happen early on in the season (you know, when they're still filming in the United States), but when Kaitlyn and the contestants traveled to Europe, they broke the mold and had one of the show's strangest ones ever in Ireland. The episode, cryptically titled "Kaitlyn's Dead," featured a group of the guys attending a fake Irish wake for her in an actual funeral home, per Vulture.

"I regret to inform you that the worst has happened," Chris Harrison explained to the men ahead of the morbid group date (via The Ashley's Reality Roundup). "Kaitlyn is dead ... for today." The contestants were even tasked with writing eulogies for their bachelorette. And although Ashley insisted this was all supposed to be "lighthearted," that was not the case for everyone involved — especially for Ben Z., who was only 14 when his mom died of cancer complications. 

As Ben explained during the "Men Tell All" episode (via Today), "Leading up to Ireland, I thought everything was great, but something happened in Ireland that forced me to close off a little bit. ... That was hard for me. It doesn't matter how much time has passed. As much as my walls came down, they came back up very quickly during that week."

As one of the most controversial contestants in "The Bachelorette's" history, Luke Parker had already alienated a lot of viewers (and his fellow contestants) early on when he declared he was falling in love with bachelorette Hannah Brown during a group date. But a few episodes later, some major red flags became apparent when the former high school football player got violent during a game of rugby on another group date. 

"Boys, I'm excited," Luke P. said when the date activity was first announced (via the Daily Mail). "I'm a competitor, so it's about to get bloody." Hannah seemed to have the same attitude, saying, "I want blood, sweat, and tears!" But unfortunately, Luke P. actually made good on that promise and ended up body slamming another contestant, Luke Stone, during the game. Calling Luke P. a "frickin' animal," Luke S. later explained, "This is the kind of guy that might, god forbid, you know, hurt someone. Luke can't control himself. ... I think at this point it's fair to say that in competitive situations, he poses a threat to other people." 

As for Hannah, she ended up in tears over the violent turn the game took (another contestant, Kevin Fortenberry, also ended up injured in a separate incident and was even taken to the hospital). "I wanted them to give their all, and be tough and tackle," she told the cameras. "But of course I don't want to see anybody get hurt."

Hannah Brown kept Luke P. around for most of Season 15 of "The Bachelorette." As she later told Nick Viall on his "Viall Files" podcast (via E!), "My relationship with Luke P., especially at the beginning, like the instant connection, reminded me a lot of my really long-term relationship and so it was like this initial attraction of like, goo goo ga ga eyes." Noting that she "really held on to that," Hannah admitted, "He's like the brightest light out there and I don't know if the light is like a 'do not come here' caution light, or like the beacon."

It certainly seemed to be the former and not the latter during the duo's fantasy suite date, however, when Hannah appeared to hit her limit after Luke P. essentially slut-shamed her for being intimate with other men on the show. According to BuzzFeed News, she responded during the explosive episode with, "Why do you have the right to do that? Because you're not my husband. You're questioning me, and you're judging me, and you feel like you have the right to, and you don't at this point. ... I'm a grown woman and can make my own decisions, and I'm not strapped to a man right now."

Perhaps unsurprisingly, Hannah sent Luke P. (who later expressed regret for his actions on the show in a since-deleted Instagram post) home that same week.

Most contestants on "The Bachelorette" seem to have tight bonds with their families. However, Dean Unglert was put in the awkward position of confronting his familial issues on camera during a hometown visit alongside bachelorette Rachel Lindsay.

Dean later explained on Instagram that his estranged father's conversion to Sikhism following his mother's death was not his point of contention, but rather his father's absence. As he told the cameras (via E!), "When mom passed away, I was a 15-year-old in my most vulnerable state in my life, and my father, my brothers, my sister ... none of us came together and came in like a moment of solidarity." Dean added, "I'm worried that my family's put on this front that we all are a big traditional happy family because at the end, everything isn't fine and cool."

For her part, Rachel revealed in a blog post written for People that she found Dean's family to be "totally welcoming and comforting" to her. Noting how she got more "insight" into Dean's past, she added how "bravely" he had handled the confrontation with his dad. Though she and Dean "ended up sharing [their] love for each other," she admittedly "cried on the entire flight home," as the experience ultimately led her to question "whether he's in a place in his life where he's ready to settle down and start a family in the near future."

Another memorably awkward hometown date came in Season 6, when Ali Fedotowsky met Kirk DeWindt's family in Green Bay, Wisconsin. This date on "The Bachelorette" seemed to be going pretty well — until Kirk's dad decided to take Ali to the basement and show off his taxidermy collection, that is. Kirk later said he was surprised to have been cut. "I actually thought the hometown date went very well, to be honest with you," he told Reality TV World. "Obviously, my dad's basement and the taxidermy thing threw a lot of people off. But as far as how she interacted with my family, I thought that had gone really well."

Although he said he initially "wish[ed]" he'd been cut before the hometown dates, Kirk and his family are ultimately happy to have appeared in the episode. "They were actually very glad it happened and it was a unique opportunity for them," he explained. "Obviously, my feelings were involved and theirs were too, but I don't think I would have it any other way. I think now that I've had some time, everybody's okay with it, they're all glad it happened, and I think it was just part of the process. So, I don't regret making it that far."

Group dates that try to take a group activity or sport and make it sexy are common on "The Bachelorette." When Clare Crawley had several of her men play a game of strip dodgeball on Season 16, however, it sparked controversy. Both Clare and then-host Chris Harrison made it clear that everyone on the losing team would have to be fully nude by the end of the game — and it upset a lot of viewers. Many fans, for example, felt the game exposed a "double standard" in the treatment of men and women in the franchise, with some who have even been involved with the show pointing out how outraged most would be if a male bachelor lead had imposed the same rules on a group of female contestants.

The game also upset one contestant who wasn't part of the group date, Yosef, who confronted Clare about the decision to impose the stripping rules, saying that, as a father, he wouldn't have participated anyway. "Number one value is to have respect for myself and my daughter," he said, according to The Hollywood Reporter. "I don't want her turning on the TV and seeing dad's a**." Clare got into it with Yosef onscreen over the criticism and later got defensive with viewers who criticized the date on Twitter, too.

While most of the dates on this list almost ruined a season of "The Bachelorette," you could argue this one actually did. Clare Crawley's time on the series ended abruptly in 2020, when she completely fell for one contestant, Dale Moss, pretty much immediately, decided to call off her search for love, and bounced with her new man not even a couple weeks into filming, according to Us Weekly. Before she officially admitted that she only had eyes for Dale, however, that fact became painfully clear to a group of contestants, when Clare basically abandoned a group date to hook up with Dale in her room.

When the other men figured out what had happened, they "threaten[ed] to leave" the show themselves, per Cosmopolitan, with one contestant saying, "If you want to go be with Dale, then we'll all go home." At one point during the sneak-away make out session, another guy came to check on Clare, knocking on her door while Dale was still in the room and prompting him to say (via The Hollywood Gossip), "Let me go hide in the closet."

It was undeniably a messy situation, even by reality TV standards. But ultimately, Clare addressed her obvious feelings for Dale, left the show way early with him (and with a ring on it, of course), and paved the way for Tayshia Adams to step in as bachelorette. Sadly, Clare and Dale called it quits in 2021.

You might assume that all of the most disastrous date moments in the history of "The Bachelorette" are long behind us, and that guys on the show have become a little more savvy in the ways of televised love. That assumption, sadly, would be wrong. During Season 18, which began airing in October 2021, bachelorette Michelle Young had a group date thoroughly ruined when none of the men seemed to notice she was even on said group date, per People. Usually, group dates are full of "Can I steal you for a second?" moments, but during a slumber party-themed day, the guys competing for Michelle's affections seemed to actively forget she was even there. Major yikes. 

This would be a hard situation for any bachelorette to handle, but it was especially difficult for Michelle, who had opened up earlier in the season about her struggles with feeling unseen growing up as a Black girl in a predominantly white community. "I was caught off-guard a little bit by the fact that I pretty much had to call the guys over," she explained (via Us Weekly). "I'm upset. Now that the boys are going to be competing against each other instead of making small moments with me during the group date." 

Michelle eventually confronted the issue with the men competing for her heart, most of whom immediately took steps to correct the problem and give her the attention she deserved.