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15 Most Awkward Moments Of The Bachelor/Bachelorette

With a new season of the Bachelor underway and 25 beautiful women all vying for the heart of bachelor, Ben Higgins, it’s fun to look back at all the memorable and just flat-out awkward moments that have taken place throughout the past Bachelor and Bachelorette seasons.

Besides giving us an excuse to drink wine on Monday nights, the past twenty seasons have given us endless entertainment. From cheesy limo exits, drama that never ends and heartbreaking blindsides no one ever saw coming, here’s a round up of 15 of these awkward moments that still make us cringe.

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15 When Jason Mesnick broke up with Melissa Rycroft on live television

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Getting dumped is hard enough without having it be broadcasted on live television. This was the case with season 13 of the Bachelor, Jason Mesnick, who went from being one of the nicest bachelor’s to some of the worst. He found himself in love with two women at the end and ended up choosing Melissa over Molly.

Yet their happily-ever-after was halted as, at the After the Finale Rose special, Jason created one of the most cringeworthy moments in Bachelor history by dumping Melissa on live TV, resulting in her calling him a "bast*rd". Then, if that wasn’t bad enough, he went on to ask out his runner-up Molly again. It worked out for the best in the end though, as Jason and Molly are still happily married and have a child together.

14 When Brooks dumped Desiree before the finale

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Usually it’ s the contestants’ who are afraid of having their heart broken by the bachelor or bachelorette. That wasn’t the case for Brooks Forester who competed for Desiree’s heart during her stint as the Bachelorette. It had even been highly speculated by Reality Steve that Brooks was the winner in the end, but it became very clear that wasn’t true after Brooks broke Desiree’s heart before the finale, leading to a very awkward fifteen-minutes of him rambling and her crying.

Some might say that Desiree settled for her second choice, Chris, but she does seem happily in love and the two are now married.

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13 When Juan Pablo shamed Clare

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Sex is a part of the Bachelor/Bachelorette series that many choose to not discuss. Yet, it happens, and it resulted in one of the most controversial moments in the show by bachelor, Juan Pablo.

During their time in Vietnam, one of the contestants and final two, Clare, snuck out at 4 a.m. to take a dip in the ocean with Juan Pablo…only they didn’t just take a dip. Many speculated that they actually had sex. All seemed well between them until the rose ceremony when Juan Pablo pulled Clare aside and expressed the regrets he had of hooking up with her as it was unfair to the other girls and because he has a daughter. Many fans were furious over Juan Pablo’s role in sl*t-shaming her on national television, thus fueling him to become one of the most hated bachelors.

12 When Jamie straddled Ben

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First kisses can be awkward, but Bachelor contestant, Jamie Otis, took it to a whole other level. Host Chris Harrison even called the kiss between Jamie and bachelor Ben, “easily one of the most horrifying moments in the history of the show.”

Jamie was known for being rather shy and prudish so it was a surprise to Ben when she decided enough was enough, she wanted to finally kiss him. It all went downhill when she said, “when I go to bed at night I definitely, uh, you know, I think about you often and I think about the things I'd like to do with you.”

Then she proceeded to straddle him and when they did finally kiss, she couldn’t stop laughing, making the entire thing awkward for them and cringeworthy as hell for the rest of us watching.

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11 Tierra’s “sparkle”

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Every season has a villain and Tierra LiCausi of Sean Lowe’s season had a “sparkly” edge to her antics. The entire season, she was unable to get along with the other girls and infamously couldn’t control her eyebrow (of which was given its own Twitter handle). Sean was always there for her, often spending his time reassuring her about their relationship and comforting her when she fell down the stairs and hit her head and then again when she apparently got hypothermia from the polar plunge they did while on a group date.

During the Women Tell-All special, Tierra explained why she seemed to be the root of drama, blaming it on her “sparkle.”

10 Andi confronting Juan Pablo post-fantasy suite

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It’s okay, it’s okay. Two words that former Bachelor contestant and Bachelorette, Andi Dorfman, never wants to hear again after her awkward encounter with Juan Pablo the night after their fantasy suite date.

Up to that point, she had been falling in love with him, but all it took was one night alone with him, with no cameras or crew around, for her realize she couldn’t spend her life with this guy. According to her, throughout the night, when he wasn’t talking only about himself, he told her that she had barely made it to St. Lucia and even talked about what went down with him and Clare. Adios, Juan Pablo!

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9 When devoted Christian, Sean Lowe, got called a “playboy.”

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Bachelor Sean Lowe was easily one of the most genuine and good-hearted bachelor’s there ever was. Not only that, but he was open in his Christian faith and considered himself a “born-again virgin.” So it was a huge shock to him—and viewers—when Desiree, one of his final three contestant’s, brother called him a “playboy” and questioned his intentions. This resulted in Sean defending himself and going on to eliminate Desiree at the rose ceremony as he couldn’t imagine a life with her while being at odds with her brother.

8 When Chantal slapped Brad

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Before Juan Pablo, Brad McCormak was the most hated Bachelor of all-time and season 15 contestant, Chantal O’Brien, let him know so. During her first time meeting him, she bravely announced that she had something for him on behalf of every woman in America before proceeding to slap him hard right across from the face. Brad looked shocked at first before breaking out into a laugh and saying that he actually liked her and that she had a good hit.

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7 How Bentley Williams played Ashley Hebert

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Before even coming in as the Bachelorette, Ashley Hebert had doubts that the guys would be happy that it was her and not Emily Maynard, who was also a fan favorite from Brad’s season.

All of these insecurities sadly came to light after Bentley Williams, a contestant on her season, played her throughout the show, leading her to believe that he actually liked her before abruptly leaving the show mid-season. Not surprisingly, even after they had a face-to-face talk, Ashley still felt betrayed by him, saying, “I cannot believe I wasted so much time on Bentley. He's such a player. He disrespected me to the core and I don't understand what I did to deserve this. Bentley, if you're watching this, f--k you, I’m done with you.”

6 The failed backflip limo exit

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The Bachelor and Bachelorette have had it all when it comes to limo exits. From arriving in a cupcake, wearing a wedding dress, pretending to be pregnant, flying in a helicopter to whipping out a 50 Shades of Grey tie, these contestants take their one shot at a first impression very seriously (and hilariously). While some of these work, grabbing the attention of the season’s lead, some epically fail. This was the case for Robyn Howard of Sean Lowe’s season who tried to do a backflip while in her dress and heels, only to wipe out right in front of him. Talk about an embarrassing first impression.

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5 Sharleen Joynt’s awkward kiss with Juan Pablo

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Sure, she can sing. But can she kiss? It didn’t seem so when the Opera singer finally locked lips with Season 18’s Bachelor, Juan Pablo. It was during the soccer group date in episode three that the two of them were sitting picnic-style on the grass. All was cute and romantic until the two locked lips and provided viewers with one of the most awkward kisses on Bachelor and Bachelorette history.

4 Jake Pavelka and Vienna Giraldi’s messy public breakup

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Perhaps in a move to extend their fifteen minutes of fame, Bachelor Jake Pavelka and his ex-fiancé Vienna Giraldi aired out all their dirty laundry on national television, resulting in one of the messiest breakups in Bachelor-history. There was crying, yelling, insult throwing and lots of potential for a spike in ratings. In the end, Vienna moved on to a different reality TV show, appearing in Relationship Rehab and Jake went on to Dancing with the Stars.

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3 Rozlyn Papa’s affair with a producer

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Bachelor contestant Rozlyn Papa may have come to the show for love, yet she didn’t find it with the season’s lead—she found it with a producer instead. The 28-year-old single mom and model had been accused of having an “inappropriate relationship” with one of the show’s producers who turned out to be married. He was fired from the show and Rozlyn was also asked to leave during the season’s second episode. She later confessed to the accusations and even came back for the Women Tell All episode, where she later said there was lots of tension between her and host Chris Harrison.

2 When Juan Pablo wouldn’t say he loved Nikki Ferrell

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Usually at the end of the Bachelor and Bachelorette season, the lead’s can finally breathe a sigh of relief as they’ve fallen in love and can finally utter the words, “I love you,” to their chosen one. That wasn’t the case for Juan Pablo, an unconventional bachelor as he didn’t propose to Nikki Ferrell and the most feelings-wise he told her was that he “really liked her.” This floored host Chris Harrison who hadn’t gotten along well with Pablo all season, and during After the Final Rose, it was extremely awkward as Harrison kept trying to get Juan Pablo to say that he loved Nikki—all while she was sitting right there. The relationship between the pair didn’t last—though Pablo did finally tell her that he loves he— and Nikki recently got engaged over the weekend.

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1 When a contestant has a boyfriend/girlfriend back home

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Nothing would be worse than discovering that your significant other has gone on to the Bachelor or Bachelorette, therefore proclaiming to the world that he or she is single as can be. This leads to the awkward moment where the truth comes out and the boyfriend or girlfriend comes back to confront their partner on national television.

This happened to several contestants throughout the series—Wes Hayden in Bachelorette season 5 shockingly had a girlfriend back home and then in season nine when Bachelorette Desiree had to deal with Brian Jarosinski and his girlfriend who came to confront him.

Sources: elle.com, wetpaint.com, wetpaint.com, usmagazine.com, nypost.com

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