The Most Cringeworthy Moments On The Bachelorette

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Are you a big fan of reality TV? Great to know it’s not just us! There’s something about watching the surreal adventures of contestants thrust into some of the craziest situations. For this reason, we absolutely love to watch The Bachelorette, a show that’s all about helping an eligible young lady find love. Sometimes it works out, sometimes it doesn’t. But even when there’s not a love match, you are guaranteed heaping helpings of juicy, juicy drama!

Arguably, the best drama on The Bachelorette comes from the cringeworthy moments that make you gasp out loud. Of course, you don’t always have time to watch a whole season in order to experience them. But that’s where we come in: we’ve assembled the most awkward moments in the history of The Bachelorette. Just keep reading to discover the biggest drama bombs in all of reality TV history!

That’s a “rap”

Everybody loves a good music video, right? The only thing that can make a great tune even better is a killer video to go with it. That’s probably why The Bachelorette agreed to create a music video for the 2013 season: they thought it would bolster the fandom, and since they got help from Soulja Boy, they probably hoped it would go viral. However, the producers should have been careful about what they wished for, because this video went viral for all the wrong reasons!

This was the season featuring Desiree Hartsock, and she drops such cringeworthy lines as “I’m the Bachelorette and I’m rapping to you poolside. Here to find true love, one man for my whole life. … Dating all these guys really ain’t that easy. I’m looking for a husband, not abs and a cheesy smile for the camera.” The whole stunt backfired, and most fans of The Bachelorette agreed this was one of the worst things the show had ever done. As for the rest of the internet, the general consensus was that this video was so stupid, they wouldn’t be checking out the show anytime soon!

Instant tattoo regret 

There’s something incredibly sexy about a good tattoo. Who doesn’t love a hot person turning their body into a perfect canvas? However, unless you spring for super expensive laser removal, tattoos last forever. Because of that, you should never rush to get ink, especially if it’s ink related to a relatively new relationship.

Unfortunately, Bachelorette contestant Kasey Kahn had to learn this lesson the hard way. In trying to woo Ali Fedotowsky during Season 6, he made a bold statement that he would always be there to “guard and protect your heart.” Matching words to actions, he impulsively got a large tattoo of a heart and shield on his wrist. When he was booted from the show after the fifth week, he claimed he “would never change” his ink because he got it for himself. Nobody bought this, and most fans agree he was crazy to rush into getting a tattoo in the first place!

Run, Rego, run

On paper, The Bachelorette is all about strangers finding true love. That’s not why most of us watch the show, however. If we’re being honest, most of us tune in to catch some messy drama. And it didn’t get much messier than in Season 6, when Ali Fedotowsky learned that contestant Justin Rego (a wrestler better known as “Rated R”) had a girlfriend, Jessica Spillas, going so far as to chat with her on the phone. After that, she confronted Rego, acting super sweet before telling the wrestler things must have “been especially difficult” for him because “you probably really miss your girlfriend in Canada.”

Instead of answering, Rego got up and walked away. This would have been pretty awkward on its own, but the wrestler kept facing obstacles, including a locked door. He then had to climb over various fountains and planters to complete his embarrassing exit. The whole time, Fedotowsky tried to get him to explain his actions before warning him he would regret what he did to her!  

Birth of a supervillain

Reality TV isn’t something that most of us watch because we want to see heroes. No, the fun comes from watching normal people deal with extraordinary drama. However, the lack of heroes doesn’t keep some people from playing the villain. The best example of this is likely Bentley Williams, who stayed on The Bachelorette for one absolutely awful reason: he wanted to torment Ashley Hebert!

You see, he realized relatively early that he wasn’t into Hebert, and he went so far as to call her an “ugly duckling” (ouch!). Later, in a confessional, things got even worse when he admitted his cruel scheme. “The guys know I’m a frontrunner, but none of them have any idea that I don’t care about Ashley. I had the opportunity, and I played everyone.” He went so far as to say his goal was “to make Ashley cry” before revealing his real concern: “I hope my hair looks okay.” He eventually quit the show and then came back, but he never showed any remorse about becoming the worst supervillain The Bachelorette had ever seen.

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