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.