The Worst Winners in 'The Bachelor' History
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The Worst Winners in 'The Bachelor' History

Olivia Jimenez
Updated March 1, 2025 17 items
Ranked By
965voters4.5Kvotes

Why do we love The Bachelor so much? Is it the drama? The chance for true love? Or is it because we love to hate on the contestants and the winners? Well, actually, it's all of the above. To celebrate that hatred, we've created this list of the worst winners in The Bachelor history.

In Bachelor history, some winners have stood out for all the wrong reasons. While not always the fault of the women themselves (cough cough men who can not commit cough cough), these winners have faced intense scrutiny for various reasons. Sometimes, it was the lack of commitment from the bachelors, leaving fans wondering if they were truly ready for a lasting relationship. In other cases, the drama brought into the house overshadowed any potential romance, casting doubt on whether contestants were there for love or just to stir the pot. Whether due to incompatible matches or high-stakes theatrics, these winners have become infamous in the annals of Bachelor lore.

Check out our list of the worst winners from The Bachelor! Vote for the women you think was the absolute worst contestant to win the show. 
 

Over 900 Ranker voters have come together to rank this list of The Absolute Worst Winners
This list is dynamically ranked based on user voting. The order reflects the consensus of our voters and is not influenced by paid placements or editorial bias.
  • Vienna Girardi
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    Vienna Girardi

    Vienna Girardi, winner of Season 14, was chosen by Jake Pavelka. Her time on the show was marked by drama and controversy, often clashing with other contestants. After the show, her public breakup in June of 2010 with Jake was highly publicized and messy, involving heated exchanges on national television. This tumultuous relationship and her polarizing personality made her a controversial winner in Bachelor history.

    337 votes
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  • Courtney Robertson
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    Courtney Robertson

    Courtney Robertson, from Season 16, left audiences stunned when Ben Flajnik chose her as the winner. Known for her manipulative tactics and frequent clashes with other contestants, Courtney quickly became one of the most disliked winners. Her unapologetic attitude and ability to stir up drama overshadowed any romantic connection she had with Ben. The couple broke up approximately nine months after the show ended.


     

    • Age: 42
    • Birthplace: Phoenix, Scottsdale, Arizona, USA
    307 votes
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  • Shayne Lamas
    3

    Shayne Lamas

    Shayne Lamas was chosen by Matt Grant in Season 12, but their engagement ended shortly after the show concluded. Critics often point to her evident lack of seriousness about the relationship and her focus on pursuing fame. The rushed nature of their romance left fans questioning the authenticity of their connection. The twosome called it quits shortly after their season finished airing in 2008. 

    Shayne went on to marry Nik Richie, an American online personality and blogger, in 2010.


     

    • Age: 40
    • Birthplace: Santa Monica, California, USA
    165 votes
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  • Whitney Bischoff
    4

    Whitney Bischoff

    Whitney Bischoff won Season 19 when Chris Soules chose her, but their relationship ended shortly after the show aired. Despite initial chemistry, Whitney's reluctance to relocate to Chris's rural hometown played a significant role in their breakup. The couple's inability to find common ground highlighted a lack of long-term compatibility from the start.

    Chris Soules was later arrested and later sentenced to two years on probation for his role in a 2017 car crash that killed an Iowa man. 

    232 votes
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  • Vanessa Grimaldi
    5

    Vanessa Grimaldi

    Vanessa Grimaldi, chosen by Nick Viall in Season 21, faced numerous challenges in her relationship. The couple struggled with differences in lifestyle and future plans, along with rumors of Vanessa's jealousy during the show, leading to their breakup shortly after the show. Their inability to align on key life decisions made her choice as a winner seem more like a temporary match than a lasting partnership.


     

    18 votes
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  • Cassie Randolph
    6

    Cassie Randolph

    Cassie Randolph was chosen by Colton Underwood in Season 23, but their relationship was filled with ups and downs. The couple left the show before the engagement finale, ultimately leaving us with the iconic jumping the fence scene. 

    The couple eventually broke up in 2020 amid personal and legal disputes, casting a shadow over her victory. The drama that unfolded post-show emphasized the instability of their connection.

    Colton came out as gay, and married his now-husband Jordan Brown in 2023. The couple have a son, Bishop, whom they welcomed in 2024.
     

    15 votes
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