Er setzt sich zu der Frau.

Note

we don't use 'with' (mit) here in German. It would mean that they both sit down together. Since the woman sits already, the man is sitting down 'to' the woman: zu.
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How do German cases work?
German has four grammatical cases: nominative (subject), accusative (direct object), dative (indirect object), and genitive (possession). The case determines the form of articles and adjectives. For example, "the dog" is "der Hund" as a subject but "den Hund" as a direct object.

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