Entertainment

The Objectively Worst Decisions In Rom-Com History  

Donn Saylor
279 votes 47 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."

Please. 

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Never Been Kissed is listed (or ranked) 2 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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Kate & Leopold is listed (or ranked) 3 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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27 Dresses is listed (or ranked) 4 on the list The Objectively Worst Decisions In Rom-Com History
Photo:  20th Century Fox

Once perpetual bridesmaid Jane (Katherine Heigl) realizes she is in love with Kevin (James Marsden), she crashes a wedding to tell him how she feels. Not content to wait until the event is over, she interrupts the wedding and declares her love in front of a roomful of perplexed strangers. 

Imagine spending thousands of dollars on your special day only to have a Katherine Heigl character hijack it to make a personal announcement about her own love life. 

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