I'm not sure I completely understand what you mean. Generally, if a word has two different meanings, you don't use it as the subject of a sentence and use one meaning for part of the sentence and the other for the second part, unless you do it as a joke. "
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wholegrainCan a given word have two different meaning in the same sentence?Much humor depends on it, yes. But there the whole sentence usually has two meanings at the same time.
CalifJimAnd my perennial favorite, showing that literal and figurative meanings cannot be mixed:What's wrong with the example? I understand it perfectly.
She left in a Cadillac and a bad mood. (in to show literal position vs. in to show figurative position)
New2grammarWhat's wrong with the example? I understand it perfectly.Well, it's very funny to a native speaker! As explained, it mixes two uses of "in".
wholegrainWhat about these?What about them? They are all bizarre. I don't see a double meaning in the first, fourth, or the last.