I think the story was truly meant to follow a growth in Theodore more so than that in the OSes or…
Judah Berl

Thanks for that excellent analysis, Judah. The thing that really jumped out at me in your observations was Samantha as a “mirror” to reflect back to Theodore his own emotionally stunted Self. I’d have to see the movie again to dig more deeply into this angle, but I suspect that in this regard, it’s possible to interpret Samantha as a projection of Theodore’s ‘shadow,’ and that their relationship is in effect a way for Theodore to bring those ‘negative’ aspects of his psyche into the light of consciousness, process them, and move forward. Hence, his final letter to his ex-wife where he IS able to express authentic emotions, as opposed to all the other letter which summoned up a kind of inauthentic set of feelings on behalf of other people.

Again, thanks. Your insights are provocative and really got me thinking about the movie again.