Q: Sentence (1) A riding academy.
Sentence (2) Academies of literature and philology.. Word: academy.
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A: different meanings

Q: Sentence (1) He is the Republican boss in Kentucky.
Sentence (2) Party bosses have a reputation for corruption.. Word: boss.
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A: the same meaning

Q: Sentence (1) Where do you stand on the War?
Sentence (2) Standing water.. Word: stand.
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A:
different meanings