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Top 10 Most Cringeworthy Moments from The Bachelorette

VO: Emily Brayton WRITTEN BY: Savannah Sher
Script written by Savannah Sher On the Bachelorette there were moments that made us go “awe!” and then, there are some cringeworthy moments that are definitely hard to watch! For this list, we’re looking at the most embarrassing and awkward moments from the US version of “The Bachelorette”. We’ve included moments like when Chad and Evan fight, Ali confronting Justin, the soul boy rap, Emily yelling at Kalon and more!
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Top 10 Most Cringeworthy Moments from The Bachelorette


Some moments on this reality show can be unbearable to watch. Welcome to MsMojo and today we're counting down our picks for the Top 10 Most Cringeworthy Moments from The Bachelorette.

For this list, we’re looking at the most embarrassing, uncomfortable and awkward moments from the U.S. version of “The Bachelorette.”

#10: Chad & Evan’s Fight

By the third episode of JoJo’s season of “The Bachelorette”, the audience was in shock that Chad was still around. From their view, it was obvious that he was this season’s villain, as he terrorized the rest of the guys while out of JoJo’s view. This guy was clearly a loose cannon, and after a group date that was supposed to be lighthearted, he attacked one of the other guys and then punched a door claiming that it “got in his way”. This whole thing was embarrassing to witness, and we were thankful that he was sent home at the end of the next episode.

#9: Ali Confronting Justin

If you’re familiar with Bachelor nation, you know there’s always going to be a contestant with a secret. In Ali’s season of “The Bachelorette”, it was revealed that Justin AKA “Rated R” actually had a girlfriend back home in Canada. As soon as she tries to bring it up to him, he says “I’m out” and attempts to avoid a conversation with her in the most ridiculous way. Justin trying to escape from Ali by heading into a restaurant and the door being locked was just the cherry on top of this cake. Him hobbling around climbing over bushes with his foot in a cast was especially painful to watch.

#8: Ian Showing His True Colors Well he surely thinks highly of himself! Ian turned on bachelorette Kaitlyn part way through the season, telling her that she wasn’t “deep” enough for him. She was understandably offended by his snobby attitude, as he made it clear that he was not the nice guy he had tried to come off as. As he’s driving away in the limo after they mutually decide that he should leave, he goes on about what a great Bachelor he would be. Lines like “I’m being punished for being an intellectual” are just pure reality TV gold.

#7: The Soulja Boy Rap

We’re betting that Soulja Boy regrets taking part in this mess. In the second episode of Desiree’s season, the gang puts together a little rap video on one of the dates. We almost have to cover our eyes while watching this one because it’s just so painful. Whose idea was this date anyway? By season nine had they run out of better date concepts? Also, considering everyone participating in this trainwreck is white, this also seems kind of racially insensitive with a little bit of perspective.

#6: Emily Tells Off Kalon

Emily was known during her season as one of the sweetest and kindest bachelorettes, but when someone spoke a negative word about her daughter, she was not above throwing down over it. The audience at home already knew Kalon was a total jerk, but she became fully aware of it when another one of the guys told her that Kalon had referred to Emily’s daughter Ricki as “baggage”. Emily is understandably furious, and dramatically asks Kalon to leave after giving him a serious talking to about what it’s like to be a single mom.

#5: When There Were Two Bachelorettes

We know by this point that the producers of this franchise will do anything for ratings and for the sake of being able to call something “the most dramatic premiere in Bachelorette history”. But even by those standards, this was taking it a bit far. Season 11 started with two bachelorettes, and the guys got to vote on which one would actually stay. Any small semblance of feminism that exists on this show was dashed when they put the power back in the men’s hands, leaving Britt in tears when she found out that they chose Kaitlyn.

#4: DeMario's Ex Showing Up

Like in many seasons of Bachelorettes past, Rachel had to deal with a guy who had some unfinished business at home. In this episode from season thirteen, DeMario’s ex girlfriend shows up, claiming that they never actually broke up. The whole situation seems a little fishy, but Rachel is put in an awkward predicament having to deal with this woman who arrives during one of the dates to stir up trouble. DeMario is clearly hiding something, and Rachel has to watch him lie right to her face.

#3: Nick’s Question After the Final Rose

While viewers never actually get to see what happens in the “fantasy suites” on the overnight dates, it’s sometimes heavily implied. In season 10, Nick and Andi chose to spend the night together, only for it to be thrown in Andi’s face on “After the Final Rose”. Andi ended up sending Nick home, and so he asks her why she “made love to him” if she wasn’t in love with him. First off, Nick, you should probably know by now that sex doesn’t always equal true everlasting love, and second, this was a totally inappropriate thing to bring up on live TV.

#2: Kasey’s Tattoo

One of the craziest contestants in Bachelor history has to be Kasey, from Ali’s season of “The Bachelorette”. With his singing, his constant reminders that he was there to protect Ali’s heart and just his general demeanor, his entire time on the show was pretty cringey. But to top it all off, he went out and got a tattoo to represent his and Ali’s relationship, which left her pretty dumbstruck. She could tell that he was possibly unhinged, so she sent him home almost immediately.

#1: The Roast Date

The idea of the guys having to “roast” the bachelorette for a date could have been fun and playful, but several of the contestants decided to hit below the belt, leaving Ashley in tears by the end of it. Making negative comments about her chest size, this is the sort of thing that could fly in 2011 but honestly wouldn’t be put on TV today. Will played into Ashley’s insecurities that the guys weren’t really there for her by implying that he had hoped he’d be dating Emily or Chantal. There is no doubt that this is the most uncomfortable moment in the show’s history.
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