Lots of food for thought there and you make a strong case for how you view the film. Your take on the riding scene especially interests me as i didn't make much of that scene originally. I'll have to watch it again but my impression was that Flora is the one who seemed enthralled by Miles' riding exploits, while Miss Giddens mostly looked afraid. Also i think there was some kind of weird music or sound effect as the camera turned up toward the sky. As though suggesting something supernatural or disturbing was happening, or at least that Miss Giddens thought so and perhaps she was more afraid of that than of Miles falling.
And yes, from the angle you are interpreting things i can see how having an older Miles in your play would make things work better. For in terms of the film, the problem i've had with that aspect is with him being so young. Which begs the question of why did they choose such a young actor? I remember though that Miss Giddens kissed Miles at the end of the movie in a way that made me feel uncomfortable, for it seemed more a lover's kiss than that of a governess kissing a child. So there is something to all this. Perhaps Miss Giddens was attracted to the ideal of innocence and could only love him, could only return his earlier kiss, once he was cut off from the Horror and could be an "innocent" again.
Yet i still continue to interpret the movie as revolving primarily around possession instead of a crazed governess. For me too many things point toward it being a ghost story, with other aspects (such as the relationship between Miles and Miss Giddens) involved in a secondary way.
Examples:
* Flora calling out to her former governess (or the other way around) moments prior to meeting the new one. It could be that Miss Giddens imagined the calls, but she only just arrived and so it is unlikely she would be hearing or seeing things at that stage unless she were crazy to begin with, but that would make for a far less interesting film. Plus, she heard the voice before she saw Flora or could have even anticipated where she might be other than at the mansion.
* Flora seems to know that her brother is returning ("Miles is coming! Miles in coming!").
* Flora mentions telling Mrs Grose that she wished there were a way to sleep in several rooms at once and this startled the old servant. But why? And why would the writers make a point of bringing this out? My guess is to indicate that Mrs Grose feared the children were in danger of being possessed (that is, if they weren't already). Flora's wish therefore strengthened this fear since being connected to the otherworld is the only way one could conceivably be in several different places simultaneously.
* Speaking of Mrs Grose, it is hinted that she both saw and heard the Horrors but tried desperately to make believe they weren't there. For instance, she told the children to pretend they didn't hear strange noises and also Flora declares that Mrs Grose is too afraid to open her eyes in the dark. Then, too, Mrs Grose chides Miss Giddens about the dangers of waking children from bad dreams. That to me is another indication of wanting to look the other way instead of confronting the "truth" of what was happening there.
* Miles recites a poem that strongly suggests a worshipful devotion to Quint. Then while still reciting it he appears to deliberately walk up to and look out of the very window through which Miss Giddens saw Quint. As though to say: "I know you saw him there and it is he who i am drawn to, am devoted to, and not you."
* Flora rows a boat after earlier indicating she didn't know how to. She was either lying or else was now acting under the influence of Jessel, enabling her to do things she could not otherwise have done.
* Then Flora danced that strange dance and afterward said it felt like someone was watching her. Who though? Jessel? Miss Giddens? Those are the obvious conclusions but this film seldom reaches for the obvious. My thought is that a Jessel-possessed Flora was dancing for Quint and it was his presence that Flora felt. A further thought is that when Flora and Miles are possessed they (their true selves) go into a sort of slumber and are aware of little that is happening. They are essentially in a dream-state. Thus when suddenly awakened from this dream it is a shock to them. In fact, I suspect that is precisely what Mrs Grose was alluding to when she said it is cruel to awaken a child from a bad dream since it can leave the child feeling shocked and deprived.
Deprived is an interesting word to use there. For why would being awakened from a bad dream leave one feeling deprived? It makes much more sense in terms of becoming un-possessed, of having something suddenly snatched away from you. This apparently proved too much for Miles, perhaps because he was more intensely attached to Quint (as evidenced by the recital) than Flora was to Jessel. Thus a greater shock. With Flora, the initial shock may have been less but after that i think she experienced something akin to withdraw symptoms due to feeling deprived of the presence of Jessel.
* Now that i think of it, the dancing was likely meant to mirror the horse riding scene. They both, for example, depicted the children performing as though for a private audience. If this is so, then it was probably a Quint-possessed Miles who was riding in order to please Jessel. It certainly looked like he was trying to impress someone (but not Miss Giddens, for he said something about how he wasn't aware that she was even there). To me it was Flora who seemed both pleased and impressed by Miles. Furthermore, it is likely that this type of derring-do is what attracted Jessel to Quint, just as her dancing may be what first caught Quint's eye, and thus both scenes could show the children being directed by the Horrors in order to recapture stirring moments from their corporal relationship.
* A final possible indication actually comes from outside the film. The Innocents was released a year or so after Village of the Damned. I haven't seen that movie (other than catching the end of it on TCM a while back) but i gather that the plot involves a group of children essentially possessed by aliens in some sense. The actor playing the lead child there is the same one who plays Miles. My guess is that this wasn't a coincidence nor is it the only connection between the films. For it seems reasonable that VOTD inspired a similar movie to be made, except with a ghostly theme instead of an alien one.
Perhaps this also explains why they went with such a young actor for Miles, since other than maybe being a little too young they knew he would otherwise be perfect for the part given the similarities between the films and the roles he would be playing.
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