Q. This may be impossible to answer, but I feel it’s important, so I’m gonna give it my best shot. This is how I would punctuate the following:
Can you believe that I said, “When she says, ‘Do you know which fruit Jim likes best: apples, bananas, or oranges?,’ tell her this: ‘Actually, I once overheard Jim say, “I only eat pears!” ’.”?!
A. Chicago style would omit the comma after “oranges,” and we would omit the period near the end, and we allow only one colon per sentence, and we would not allow the final exclamation mark, and I seriously doubt that any editor here would let a sentence like that into a book—but otherwise, your styling is perfect. Here’s a simpler version, just for fun:
Can you believe that I said, “When she says, ‘Do you know which fruit Jim likes best—apples, bananas, or oranges?’ tell her that, actually, I once overheard Jim say that he only eats pears”?