Random Best Movies Where the Guy Doesn't Get the Girl (20 items)

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  (#17) Dumb and Dumber

  • Film

  How many of us thought that dimwitted Lloyd was actually going to score with Mary (Lauren Holly) after he and Harry (Jeff Daniels) travel all the way to Aspen to return her briefcase? Lloyd did claim to feel a connection. Of course, chicks don't dig guys with low IQs and bad bowl cuts, even in the movies.
  
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  (#12) Chasing Amy

  • Film

  What happens when a straight dude falls in love with a lesbian? He gets dumped not once, but twice. Even someone who looks like Ben Affleck can't fight human nature.
  
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  (#4) (500) Days of Summer

  • Film

  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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  (#19) Up in the Air

  • Film

  Imagine a world in which someone who looks like George Clooney doesn't get the girl. It seems unfathomable, but that was the case in Jason Reitman's love story about two frequent fliers. This is yet another case of marriage getting in the way of romance.
  
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  (#9) The Bodyguard

  • Film

  And I will always love you. That sentiment might be true for Rachel (Whitney Houston) and Frank (Kevin Costner), but the diva and the bodyguard who saved her life were simply not built for happily ever after.
  
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  (#3) Casablanca

  • Film

  "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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