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The date goes well, but Theodore hesitates to promise when he will see her again, so she insults him and leaves.

Theodore mentions this to Samantha, and they talk about relationships.

Theodore reluctantly agrees, but is overwhelmed by the strangeness of the experience.

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Theodore is fascinated by her ability to learn and grow psychologically.

Theodore confides to Amy that he is having doubts about his relationship with Samantha, and she advises him to embrace his chance at happiness. Samantha expresses her desire to help Theodore overcome his fear, and reveals that she has compiled the best of his letters (written for others) into a book which a publisher has accepted.

Theodore takes Samantha on a vacation during which she tells him that she and a group of other OSes have developed a "hyperintelligent" OS modeled after the British philosopher Alan Watts.

Theodore asks her if she is simultaneously talking to anyone else during their conversation, and is dismayed when she confirms that she is talking with thousands of people, and that she has fallen in love with hundreds of them.

Theodore is very upset at the idea, but Samantha insists it only makes her love for Theodore stronger.

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