I feel this could work as a double feature with When Harry Met Sally
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The Shop Around the Corner 1940
A very sweet love story that ends nicely on Christmas eve. I really love Jimmy Stewart character in this, towards the end, he really does remind me of some Hugh Grant's characters in Richard Curtis's films.
I would say that the Matuschek company was the less interesting part of the story. I imagine this works better on the stage. But overall I think this works a lot better than You've Got Mail (1998).
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It Happened One Night 1934
I wonder how many films owe their story to this one. I just didn't think it would be Shrek.
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