The Objectively Worst Decisions In Rom-Com History  

Donn Saylor
267 votes 45 voters 1.7k views 15 items

List Rules Vote up the decisions that would result in a crappy ending in real life.

Romantic comedies are usually meant for little more than silly fun and entertainment. Nevertheless, most of us still wonder about those romantic comedies in which characters make awful decisions. Some romantic comedy plots are so outrageous they could really only hold up in a rom-com universe. A little fantasy and escapism are always nice at the movies, but when you're dealing with the worst choices ever made in rom-coms, you generally aren't left with a satisfying happily-ever-after ending. Even the worst romantic comedy tropes pale in comparison to these terrible decisions. 

The rom-coms gathered here run the gamut from modern classics to largely forgettable fluff, from multimillion-dollar box-office smashes to big-time bombs. But they all have one thing in common: They contain some of the worst decisions made in rom-com history. 

Jerry Maguire is listed (or ranked) 1 on the list The Objectively Worst Decisions In Rom-Com History
Photo:  TriStar Pictures

Dorothy (Renée Zellweger) makes a few bad decisions over the course of her relationship with the title character, Jerry Maguire (Tom Cruise). First, the single mother quits her stable job to follow Jerry to his startup.

Next, when the startup falters, she has an opportunity to take a stable job with benefits elsewhere. However, Jerry proposes to her to get her to stay, and she says yes.

Finally, Jerry treats her terribly, only to come to her in the eleventh hour and apologize. Of course, she forgives him because he, "had her at hello."


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Kate & Leopold is listed (or ranked) 2 on the list The Objectively Worst Decisions In Rom-Com History
Photo:  Miramax

Kate & Leopold is a time-travel romance with a happy ending that hangs on one terrible decision. Kate (Meg Ryan) meets the third Duke of Albany, Leopold (Hugh Jackman), who travels to modern-day New York City from 1876 via a temporal portal at the Brooklyn Bridge.

Confusion and culture clash unfold before the couple falls in love and Kate willingly forgoes her life in the modern world to marry Leopold in 1876 - before women have the right to vote, control their own bodies or finances, or work in certain fields. 

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Never Been Kissed is listed (or ranked) 3 on the list The Objectively Worst Decisions In Rom-Com History
Photo:  20th Century Fox

Josie (Drew Barrymore) is a 25-year-old undercover journalist posing as a high school student to write about life as a modern teen. Although pretending to be a teenager is questionable in any context, what makes the decision truly disturbing is the fact that her English teacher Sam (Michael Vartan) falls in love with her.

Regardless of their attraction to each other, Sam is under the impression that Josie is a teenager under his supervision. 

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Grease is listed (or ranked) 4 on the list The Objectively Worst Decisions In Rom-Com History
Photo:  Paramount Pictures

Straight-laced Sandy (Olivia Newton-John) and bad boy Danny (John Travolta) are from two very different worlds. But by the end of Grease, Sandy decides to change her wardrobe and her personality to win Danny's heart. 

Gone is the goody-two-shoes and in her place is a cigarette-smoking, big-haired dominatrix. Altering key aspects of yourself and your personality are not hallmarks of a lasting relationship, but in the rom-com universe, Sandy's metamorphosis means her and Danny get to live happily ever after. 

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