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

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  (#1) Captain America: The First Avenger

  • Film

  Being a superhero ain't easy, just ask Captain America. How often do heroes have to give up true love in order to save the day? Captain America (Chris Evans) falls for Peggy (Hayley Atwell) while he's fighting Nazis. But in the end, he has to make the decision to save the world from Red Skull, at the expense of his love life. Is there anything lonelier than being a hero?
  
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  (#2) Cast Away

  • Film

  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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  (#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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  (#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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  (#5) Gone with the Wind

  • Film

  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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  (#6) Star Wars

  • Film

  Thank goodness the guy didn't get the girl in Star Wars! Luke and Leia did sorta seem perfect for each other, but thankfully, by the end of Return of the Jedi, the twins find out their true identities before any funny business could happen.
  
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  (#7) Big

  • Film

  She could have gone with him. When Josh's (Tom Hanks) wish is granted to return to being just a kid at the end of the comedy classic, he offers Susan (Elizabeth Perkins) the opportunity to join him in youth. Although the stern businesswoman is tempted, she contends that one childhood was enough.
  
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  (#8) Batman Begins

  • Film

  Sometimes (sigh) love must be sacrificed for the greater good. Rachel (Katie Holmes) knows that the city of Gotham needs Batman, even at the expense of their romance. If a superhero can't get the girl...
  
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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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  (#10) The Phantom of the Opera

  • Film

  The famous Andrew Lloyd Weber musical was adapted for the big screen in 2004, but even in the movies, the deformed Phantom (Gerard Butler) does not get the girl of his dreams. All those voice lessons the Phantom gave to Christine (Emmy Rossum), and he still can't close the deal.
  
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  (#11) My Best Friend's Wedding

  • Film

  Okay, so this is technically a movie where the girl doesn't get the guy. Julianne (Julia Roberts) is in love with her best friend Michael (Dermont Mulroney), but here's the hitch: he's getting hitched to Kimmy (Cameron Diaz).

  Julianne makes a fleeting attempt to ruin their nuptials by confessing her love, but in the end realizes that Michael and Kimmy are actually perfect together.
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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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  (#13) Pocahontas

  • Film

  Sometimes even in Disney movies the guy doesn't get the girl. Captain John Smith sails to the New World and falls in love with Pocahontas of the Powhatan Tribe. They come from worlds that could not be further apart, yet sparks fly and romance fills the air.

  When John asks Pocahontas to go back to England with him after he is severely injured, she declines her true love in order to stay with her tribe.
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  (#14) The Terminal

  • Film

  Another movie where Tom Hanks can't get the girl! This time she's a flight attendant named Amelia (Catherine Zeta-Jones) who helps Viktor get out of the airport after being stranded there for months. The pair share a makeshift romantic dinner and a single kiss, however Viktor will go back home to Krakozhia alone.
  
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  (#15) Lost in Translation

  • Film

  Is it crazy to think that middle-aged and bitter Bob Harris (Bill Murray) could have gotten recent college graduate hottie Charlotte (Scarlett Johansson) in Sophia Coppola's second feature film? Another romantic movie where there is no actual bedroom romance.

  Instead, we get to see the exploration of loneliness, an odd friendship, a secret unheard, and one single kiss.
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  (#16) The Break-Up

  • Film

  You know how when the couple breaks up in a romantic comedy, you feel okay because you're sure that in the end they will work things out by professing their shortcomings and admitting their mistakes? Although we expect that Gary (Vince Vaughn) and Brooke (Jennifer Aniston) will make up after their horrific breakup, it never happens, even after Gary tries to win Brooke back.

  She simply knows that she can't give anymore to the relationship, even if ending their union is totally heartbreaking.
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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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  (#18) The Way We Were

  • Film

  Politics really do ruin everything. Audiences knew deep down that the Marxist and the Wasp were probably never going to make it, but we fooled ourselves into believing in true love even after Katie (Barbra Streisand) and Hubbell (Robert Redford) got divorced.

  It wasn't until the couple ran into each other on the street in a chance meeting years later that their goodbye finally resonated as permanent. Cue the tears and grab the tissues - it's hard to accept that some things are simply not meant to be.
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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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  (#20) Once

  • Film

  Why, oh why did these two not get together? Sometimes there is heartbreak, even without romance. “Guy” (Glen Hansard) and "Girl" (Markéta Irglová) make such pitch-perfect beautiful music, but each has other relationship commitments that they can't let go of. Damn you husbands and girlfriends.
  

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