Romantic Movies The Best Movies Where the Guy Doesn't Get the Girl  

Ann Casano
6.8k votes 1.3k voters 126.2k views 28 items

WARNING! Potential spoilers on this list.

We’ve been trained by Hollywood to expect that the guy will always get the girl at the end of the movie. The couple will be greater than their differences, overcome their enormous obstacles, and fight against all odds to stay together in order to live happily ever after. That’s how all great romantic movies end, right? Yes. Except when they don't.

This is not a list of films where relationships end because someone died like in Love Story. Instead, this list ranks the best movies and rom coms that dare challenge Hollywood conventions and shove past genre codes, even at the expense of audience delight. In these movies, the guy doesn't get the girl, there isn’t a happy ending, and we can’t imagine a future filled with children and Disney vacations.

Sometimes romantic comedies and other films about relationships are actually like real life. And in real life, most relationships simply don't work out. Not every couple is meant to overcome their differences (The Way We Were), not every couple can fight against uncontrollable odds and stay together (Casablanca), and not every couple is meant to last for the long haul (500 Days of Summer).

We might cry at the end of Casablanca every time we see Bogey watch Bergman get on that plane, but admit it, doesn’t the bittersweet ending help to make Casablanca one of the best films ever made? Life isn’t all about happy endings anyway. There has to be some truth, even in our entertainment. So vote up the best movies about in which guys don't get the girl and hope that your own attempts at true love are more successful.

Casablanca is listed (or ranked) 1 on the list The Best Movies Where the Guy Doesn't Get the Girl
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1 458 VOTES

"Here's looking at you kid." Rick (Humphrey Bogart) kisses Ilsa (Ingrid Bergman) goodbye and audiences bawl their eyes out. Yes, they will always have Paris, but why, Rick, why did you send her away?! Why?!

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#8 on The Very Best Oscar-Winning Movies

#85 on 'Old' Movies Every Young Person Needs To Watch In Their Lifetime

#19 on The Greatest World War II Movies of All Time

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(500) Days of Summer is listed (or ranked) 2 on the list The Best Movies Where the Guy Doesn't Get the Girl
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2 537 VOTES

Just like in Annie Hall, we know right from the beginning of Marc Webb's postmodern, non-linear love story that Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel) do not wind up together in the end. The narrator tells us, "This is a story of boy meets girl, but you should know upfront, this is not a love story."

It's true that sometimes the cynic and the dreamer are just not meant to be and it's heartbreaking to watch Tom wallow in his misery, that is until he meets Autumn (Minka Kelly) during a job interview, and the tides of love seem to change with the season.

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#36 on The Greatest Date Movies of All Time

#64 on Movies That Should Be Made Into Broadway Musicals

#6 on 50+ Quirky Romance Movies That Are Unique in Their Own Way

#72 on List of Movies Like Inception

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Cast Away is listed (or ranked) 3 on the list The Best Movies Where the Guy Doesn't Get the Girl
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3 453 VOTES

No, this isn't about Chuck (Tom Hanks) losing dear Wilson, although that is perhaps one of the most tragic events in the film. Chuck's girlfriend Kelly (Helen Hunt) thought he was dead, and though she searched for him after his disappearance, after four years she moved on to marry another man.

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#34 on The Top Tearjerker Movies That Make Men Cry

#53 on The Greatest Epic Movies Ever Made

#52 on The Greatest Movies for Guys

#49 on The Best Rainy Day Movies

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Gone with the Wind is listed (or ranked) 4 on the list The Best Movies Where the Guy Doesn't Get the Girl
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4 346 VOTES

An epic story of romance during the American Civil War, a Southern belle and an outsider fall madly in love. But Scarlett (Vivien Leigh) turns Rhett (Clark Gable) away, then begs him to come back to her. The guy doesn't get the girl in the end, because he frankly didn't give a damn about her crying pleas that she never stopped loving him.

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#84 on The Best War Movies Ever

#2 on The Very Best Oscar-Winning Movies

#25 on The Greatest Chick Flicks Ever Made

#9 on The Best Movies Based on Books

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