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Be it either whilst writing or reading, I've not come by an easy way to comprehend the use of the 'that that' lexical ambiguity, taking into account that improper use of punctuation is not the issue.

Is there an example anyone could cite (and link if possible) that doesn't affect the flow of the prose itself to the reader?

  • He said that that won't do.

  • I think that that is the best choice.

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    This is really a matter of opinion ... I don't think that these examples are that hard to understand. Note that the two thats are pronounced differently in many dialects. Possibly people who pronounce them the same use this construction less. – Peter Shor Feb 8 '15 at 11:11
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    What level are you aiming at? French has different words for the complementiser and the demonstrative pronoun usages (que, and ça etc). You could compare "I think that that is the best pub in town" with "I think that that's the best pub in town" and "I think that this is the best pub in town." (I've changed the example slightly to get further from the "should we use 'this', 'that' or either in this sentence?" complication.) – Edwin Ashworth Feb 8 '15 at 11:52
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Oftentimes the problematic "that" is superfluous and can simply be removed (especially colloquially). For example, instead of "I think that that is the best choice," just say "I think that is the best choice."

Another option is to eliminate "I think that," and simply state the opinion that forms the most important part of the sentence: "That is the best choice." Oftentimes it is presumptively the case that what a speaker says is his own opinion. Of course, context may make this approach unsuitable (e.g., where the speaker is emphasizing that the opinion is his own).

There are plenty of other ways to restructure as well. "According to him, ..." instead of "He said that," for example.

  • I don't agree with your first paragraph. "I think that that man doesn't know what he's talking about" doesn't have a problematic "that" -- and in writing, it is less confusing than "I think that man doesn't know what he's talking about." – ruakh Feb 8 '15 at 19:26
  • @ruakh: You mean that without the second "that" it's ambiguous — it might be taken to mean that "mankind doesn't know what he's talking about"? – Peter Shor Feb 8 '15 at 23:39
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    @PeterShor: Right. And even if it hadn't been completely ambiguous, it could still lead you down the garden path. ("He had a very difficult childhood, and I think that childhood is part of why he turned out the way he did.") – ruakh Feb 8 '15 at 23:49

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