Bachelorette’s 10 Most Embarrassing Moments


Over the years our favorite bachelorettes have been faced with their fair share of awkward situations. Sometimes they make us cringe and other times, we can’t help but bust a gut. This list takes a look at some of the most embarrassing moments of our beloved Bachelorette series.

10. Wes Hayden and the Girlfriend Situation

Poor Jillian was mortified to find out that the front-running, ultra-suave musician Wes Hayden had a girlfriend back home on season 5 of The Bachelorette. While this whole girlfriend waiting in the wings thing has now become an expected feature of the show, at the time this happened it was simply shocking! Wes has yet to break into the mainstream music circuit, but he has gone down in history as one of the most hated contestants of all time!

ABC/Adam Larkey

9. Bentley

When Bentley appeared on Ashley Herbert’s season of The Bachelorette a new brand of villain was born. Ashley questioned Bentley’s motives early on after receiving a text message from previous Bachelor contestant Michelle Money. Michelle said that Bentley was on the show simply to promote his business. Ashley fell hard for the bad boy who was busy saying all sorts of terrible things behind her back. He compared planning a wedding with Ashely to “swimming in pee” and stated, “I came in thinking Ashley wasn’t attractive at all.” Charming! He got his though! Ashley sent him packing with a giant “f*ck you!”

8. Brooks Quit the Show

Desiree Hartsock is one of the most beloved bachelorettes of all time and when the clear front-runner, Brooks Forester, broke her heart for the world to see, we couldn’t help but ache for her! Desiree was humiliated when Brooks took her aside to break the news that he just wasn’t that into her. That’s always hard to hear, but on national television? Ouch! The debacle made Desiree question the entire process, but in the end she chose Chris, and the two are still happily married. Guess all’s well that ends well!

7. DeAnna Pappas’ Horrific Grammar

Throughout season 4 of The Bachelorette, DeAnna Pappas constantly made simple mistakes in grammar that left audiences wondering where her head was at. It had become such a joke with producers and crew from the show that a series of outtakes were included in her blooper reel where producers were actually telling her the right words to complete her sentences. Case in point, “I did felt a little awkward” and “The relationship that Jeremy and I have, has continuously growed…” which she corrected to “grew” before being told it should be “grown.” Someone get this woman a book!

© ABC / courtesy everett collection

6. Nick’s Sex Talk

Nick Viall made the world gasp along with bachelorette Andi Dorfman when he confronted her on The Bachelorette: After the Final Rose for what/who went down in the fantasy suite! He asked her, “If you weren’t in love with me, why did you make love with me?” Bah, recoil! Andi got pissed and it was clear that she was humiliated and offended by his forwardness. Luckily, her fiancé Josh took it all like a champ and appeared on stage as though nothing had happened. Nick went onto more embarrassing moments on Kaitlyn’s season of The Bachelorette. You all know what I’m talking about! Yikes!

5. Good Ol’ Drunken Tim

Ashley Herbert was such a sweet bachelorette, but she had to take some initiative and send Tim McCormick home after he got more than just a little tipsy. The drinks were flowing freely and Tim gradually became increasingly belligerent. He chirped masked man Jeff, but it was his behavior that was the truly embarrassing part of the night. He wound up being carried off to a van to make his exit even before the rose ceremony could get started. Epic fail!

4. Emily Brings It

No one expected Malibu Barbie aka Emily Maynard to bring the heat when Kalon McMahon referred to her daughter Ricki as “baggage.” But Emily let loose on him in a way that became a thing of legends after Doug Clerget told her what Kalon had said. After her rant with her momma claws out she instructed him to “get the f*ck out” and solidified her place as on of our favorite bachelorettes ever!

3. Kasey Gets Inked

In a desperate attempt to win Ali Fedotosky’s heart, Kasey Kahl went to the extreme and got a wrist tattoo to demonstrate his commitment to “guard and protect her heart” on season 6 of The Bachelorette. He also decided that it was a good idea to try to woo her with some sweet serenading. Yikes! Obviously, Ali got spooked and sent Kasey packing, while the audience was busy recovering from wincing over his embarrassing efforts.

2. Ian’s True Colors Show Through

Back on Kaitlyn’s season of The Bachelorette, audiences got to meet Ian. The guy made a great first impression but that didn’t last long. He went on and on about how humble and deep he was until he got the boot from Kaitlyn. And while having an inflated ego should have been hugely embarrassing, it just wasn’t enough. Ian got into the limo and declared that he should be the next bachelor and he’d ‘bring them out of the woodwork.’ Classy! He went on to state, “Oh man. I need to have some sex.” That’s deep!


1. “Jo! Jo! Jo!”

The gimiks people come up with to make an impression are going to new extremes with ever season, and on this season of The Bachelorette, Nick B. showed up as Santa Claus. Saint Nick…get it? Wah wah. What could only make things worse was his sad attempt at a pun and his constant repeating of “Jo Jo Jo!” For the love of god, why? But all of this strangely didn’t seem to dissuade JoJo and she sat on his lap, happily accepted a gift (I need to know what it was!), and gave him a rose at the ceremony.


Jessica Bowden