‘The Bachelorette’

07.31.11

The Bachelorette’s 6 Most Humiliating Moments

Ashley Hebert declares her true love on The Bachelorette’s Monday finale, but her quest for romance has been anything but a rose ceremony. From insults about her chest to getting dumped on a boat, WATCH VIDEO.

The Bachelorette Gets ‘Played’

So much for not crying in the special “Men Tell All” episode. Hebert failed to keep it together when asked by host Chris Harrison what the toughest part about watching herself on television was. Here, she confesses that feeling like a fool after being “played,” being called an ugly duckling, and just being criticized by the public in general really weighed heavily on her. But the hardest part, in fact, was seeing how much time she wasted. It’s an interesting, if not awkward, regret for a reality television star who some would argue wasted more than 20 hours of our time during the entire season.

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The Roast Heard Around the World

Roasting comes from “a place of love and affection,” in the words of comedian and Bachelorette roast master Jeffrey Ross. If Ross’ words are true, then Episode 3's  group date showed bachelorette Ashley Hebert lots of love—or at least it should have. In an outing to a comedy club, the contestants were challenged to show off their performance chops by roasting the flame-haired woman of the hour, herself a rejected Bachelor contestant. The roast, performed before a packed house, started with good-natured jabs but quickly turned humiliating when Hebert’s suitors took pot shots at her chest size, called her the previous Bachelor’s “leftovers,” and compared her to the previous season’s winner, Emily Maynard. “It’s been a rough day…When it rains, it pours,” Hebert later conceded of the date that left her in tears—and left the audience cringing.

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The Least Eligible Bachelor of All Time

The Bachelor and Bachelorette franchises are no stranger to broken hearts and manipulation, but Hebert’s season featured a new breed of single villain: Bentley Williams. Early on in the season, Hebert questioned Williams’ motives, thanks to a text from former Bachelor contestant Michelle Money, who said he was appearing on the show just to promote his business. The text, however, was just the beginning of his backstabbing. Williams would go on to compare planning a wedding with Ashley to “swimming in pee” and regularly made disparaging remarks behind her back, including this gem: “I came in thinking Ashley wasn’t attractive at all.” Hebert fell hard for the bad boy, but in a surprise standoff later in the season, Williams got what he deserved: A “f—k you” on national television. Every rose has its thorn, but some, apparently, are hiding more than others: Watch Bentley break Hebert’s heart by leaving the show because he missed his daughter—or so he says.

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Sealed with a Diss

What could be more embarrassing than getting shot down in the bedroom? Try getting shot down on national television. After a bumpy ride, Hebert and her three final suitors went on a getaway to Fiji in Week 9 of the show. The South Pacific island should have had all the makings of the “ultimate place to fall in love,” in Ashley’s words, but might have been more aptly described as the ultimate place to get dumped. On a date when Ashley was supposed to spend the night with the man of her choice, Constantine Tzortzis, the unlucky in love bachelorette went home alone after the 30-year-old Atlanta native said he had too much “respect” to bed her.  “This fancy suite, I know what it means. I also know what it implies,” Tzortzis said over dinner. “And if I got to this point and I wasn’t in love with you, I wouldn’t accept the fancy suite.” He took the high road—at least compared to bad boy Bentley—and departed the show immediately after coming clean.

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Ashley Hebert, Who?

Hebert landed the coveted spot of bachelorette after she was rejected on the previous season of The Bachelor, when troubled hunk Brad Womack passed her up for blond bombshell Emily Maynard. But comparisons to Maynard, who eventually split with Womack, didn’t end for Hebert after the previous season’s rose ceremony rejection. Maynard might as well have made an appearance on The Bachelorette, what with all the cast mates pining for the Bachelor winner. To assuage Hebert’s doubts, the contestants made half-hearted attempts at reassurance. “One man’s trash in another man’s treasure,” William Holman said of Womack’s choice. We’re guessing that didn’t make Hebert feel better.

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A Rejection of Titanic Proportions

Can’t a girl at least get dumped on dry land? Bentley Williams might have kicked off the premature departures, but Mickey McLean brought new meaning to the phrase “rock the boat” on a trip to Hong Kong. After Ashley whittled her suitors down to seven, Williams made an unexpected return halfway around the globe to bring some closure to his earlier departure. The Bachelorette’s villain left early on in the season because he wasn’t interested in Hebert, but he said he wanted to keep the possibility of a relationship open between the two. Although Hebert told Bentley off with the “f—k you” heard ’round the world, their secret rendezvous didn’t go over well with some of the other bachelors, including McLean. The 31-year-old chef was so unhappy with news of Williams’ brief return that he stormed off the show mid-date—on a boat. Let’s just say his rose went overboard.

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