‘The Bachelor’: Most Shocking Finales, From Jason Mesnick to Colton Underwood

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ABC

Was Colton Underwood's shocking two-night Bachelor finale the most dramatic in franchise history? 

For four hours, Bachelor Nation watched as the philanthropist followed his heart through shows of unbelievable athletic ability (he hopped an eight-foot fence!), blindsiding breakups and many, many tears.

Fans were on the edge of their seats wondering if Underwood would ever find love or lose his virginity, but when host Chris Harrison mentioned that his split from frontrunner Cassie Randolph was the most devastating in history, viewers tended to disagree. 

Over The Bachelor's 23 seasons, we've had quite a few headline-making finales, filled with switcheroos, non-proposals and even one man dumping both his final two in favor of flying solo. Check out the show's biggest shockers below: 

Alex Michel

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ABC

Long before fans expected a fairy tale proposal at the end of The Bachelor, there was Alex Michel. While there was no status quo to stray from, Michel’s finale upset fans after rejecting America’s sweetheart, Trista Sutter (nee Rehn), hours after Harrison had been told that Michel was going to get down on one knee. Michel ended up picking Amanda Marsh at the last minute, and Sutter went on to become the Bachelorette.

Bob Guiney

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ABC

Bachelor No. 4, Bob Guiney, didn’t propose either. He instead offered his final pick, Estella Gardinier, a promise ring -- but it seems his promise was only to keep dating for a few months. Guiney later dumped Gardinier via phone call.

Charlie O’Connell

Who can forget the season Jerry O’Connell’s little brother was the Bachelor? Maybe a few of us, because it happened all the way back in 2005. O’Connell didn’t want to play by the rules during his season (not that there were many on season seven), so his finale saw him ask both Sarah Brice and Krisily Kennedy to continue dating him in the real world for the next several months. At the show’s After the Final Rose special, he decided his heart was with Brice -- but still didn’t get down on one knee. The two dated off and on for the next five years, before calling it quits.

Brad Womack

While each Bachelor’s finale had at least appeared to end happily for a few months (or weeks), Womack shocked the world by rejecting both women at the end of his first season as the Bachelor in 2007. Both Jenni Croft and DeAnna Pappas were sent home in tears, even after Womack called Pappas’ father to ask for her hand in marriage. Womack quickly became public enemy No. 1, until semi-redeeming himself with a second shot at love in 2011.

Jason Mesnick

Call him Arie 1.0. Jason Mesnick became the most-hated Bachelor in history after originally proposing to Melissa Rycroft, only to break up on After the Final Rose and ask his runner-up, Molly Malaney, if she’d give him a second shot. She did, they got married in 2010, and the world forgot all about his drama. 

Jake Pavelka

Most of Jake Pavelka’s drama happened after his season finale, but that doesn’t mean he didn’t make headlines. The pilot famously left fan favorite Tenley Molzahn in the dust for the season’s villain, Vienna Girardi -- only to have their emotional, cringeworthy breakup play out on a special during Ali Fedotowsky’s season of The Bachelorette months later.

Ben Flajnik

Ben Flajnik followed suit in 2012, proposing to his season’s villain, Courtney Robertson. The pair broke up before Women Tell All but got back together in time for After the Final Rose -- so we could see their relationship drama play out on live TV. Flajnik and Robertson’s reunion was probably one of the most awkward in history (shout-out to Nick Viall and Vanessa Grimaldi!), with the two admitting that they didn’t know what the future held. Spoiler: they broke up, she started a fling with our current Bachelor, Luyendyk, and called him the best sex of her life.

Juan Pablo Galavis

After firing fans up with some not-so-nice comments throughout the season, America wasn’t exactly on board with Galavis' season finale -- but neither was he. After his dramatic breakup with our new feminist icon, Clare Crawley, who shut him down so hard -- he revealed it was Nikki Ferrell whom he wanted to… date. He liked her “a lot,” he just didn’t love her -- and even refused to say the L-word on After the Final Rose. No surprise here: their relationship didn’t last.

Arie Luyendyk Jr. 

Before Underwood, Bachelor Nation was still reeling from Luyendyk's famous switcheroo. The race car driver proposed to Becca Kufrin on his season finale, only to decide weeks later that he actually wanted to pursue a relationship with his runner-up, Lauren Burnham. Fans watched Luyendyk and Kufrin's brutal unedited split on his season finale, before he brought out Burnham and proposed to her on After the Final Rose -- becoming the first Bachelor to get engaged twice in one season. It all did have a happy ending, however, as Luyendyk and Burnham tied the knot in January, with Kufrin happily engaged to her final pick from her season of The Bachelorette, Garrett Yrigoyen.

Colton Underwood 

The former football player went where no Bachelor had gone before in his finale, when he went from three women to zero, then back to one! After his favorite gal, Cassie Randolph, broke up with him at final three, he jumped a fence and quit the show. He was located in the Portuguese countryside soon after, and eventually agreed to come back, break up with the remaining women left, and chase down Randolph. The aspiring speech pathologist was nowhere near ready to get engaged, but that was fine with Underwood, who decided they should just date. 

See more in the video below. 

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