I think all the angst was plausible this episode. As was stated earlier, he's trying.
Loved the movie part too!
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Don't you just love how art imitates life? She gets to tell her whole story, and it is only a movie. He gets to be her lover, and it's only a movie. I think this way is much more endearing than how Please! Teacher was done. There is no basic taboo of a teacher student relationship. But it is still the unusual premise of older woman, younger man. Although I do not think she qualifies to be a cougar, not while still in high school.
And as far as movies in an anime, I think the movie they are making will be more interesting to watch than the one from Haruhi. More Kubrick, less Corman or Troma studios.
newy EDIT: Don't double post