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John Shepard had always loves the Princess Bride. The sword fight scene being part of what made him want to learn to fight hand to hand in the first place. Also his sense of humor was widely devolved, by the films witty banter. John always had felt that most problems in life could be solved by quick think , physical force, and witty banter. Something he would never admit to least of all to Elizabeth was that the love store was at the heart of his true love for the film.Yes it is true John Shephard is a romantic and he ships Wesley/Buttercup hardcore.
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Buttercup had always loved the stars. After Wesley had been reported dead the stars where the only thing that consoled her.Looking up at them she would dream of a man like her Wesley quick thinking, brave and with eyes like a sea after a storm. He was out there somewhere sailing between stars. He would sail to her star one day and say "hello my name is John Shephard, Run." Yes buttercup dreamed of a Doctor name John Shephard.