I think you're only looking at the physical aspect. Theodore wants a "purposeful" connection, something with more than a sexual component, such as he had with his ex-wife. In the somewhat dystopian world he occupies, nearly everyone keeps to themselves and stay inside themselves. Real communication between people seems cropped and sanitized. Theodore struggles to find meaning in all this, despite his talent for writing heartfelt letters that speak to the soul. He wants more than what's all around him. Sure he's got typical male attitudes and almost has sex with his date. That moment of realization that they're drunk and the starkness of the mood change in that scene with Wilde was jarring. She wants more but he's not what she's looking for and he wants more, yet she's not what he's wanting either.
Samantha is that sudden constant, that interactive one who sees him and talks to him when he's away from that world at home and then sometimes outside in that world. She knows his hopes, his dreams, his struggles, his faults and his gifts.
This movie came across to me as a bitter-sweet romantic story that does have a strangely pleasing end. It's a rare, very thoughtful and introspective movie that I believe is a looking glass into our very near future.
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