Consider this example:

That 'that' that that guy used was ungrammatical.

The four instances of "that" are all grammatical, but have different functions/meanings. What is the function/meaning of each "that"?

  • this page might be a start. – user6951 Jul 13 '14 at 14:55
  • Determiner, noun, relative pronoun, determiner. – Damkerng T. Jul 13 '14 at 15:01
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    Although there's an argument to be made that that that that Damkerng refers to as a relative pronoun is in fact the same marker of subordination we find in non-relatives and is not a relative pronoun at all. – snailplane Jul 13 '14 at 15:07
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    Compare to: "That thing that those guys used was ungrammatical." – F.E. Jul 13 '14 at 18:25
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    @CoolHandLouis F.E. has made his point clearly enough already. Did you misread his comment? Those, like the fourth that, is a distal demonstrative determinative. Those guys is syntactically very similar to that guy. It makes it clear which that is being used by substitution with a less ambiguous word of the same type with the same function. – snailplane Jul 13 '14 at 19:24

It may be difficult for non-native English speakers to even understand the question (which is important since StackExchange is intended to be a resource). So let's build up the semantics one "that" at-a-time, which, incidentally, will also answer the question.

  • 1st That: That flower looks pretty. The first that is a demonstrative determiner, indicating which flower is being talked about.1

  • 2nd That: That "that" should be capitalized. The second that is simply a reference to the word itself, so it is a noun. For example, consider the following incorrectly capitalized sentence written by some student in a paper: John thought, "that is interesting." A teacher, talking to the student, might point her finger at the word 'that' and say, "That 'that' should be capitalized."

  • 3rd That: That milk that he used is sour.2 The 3rd that is a relative pronoun introducing a relative clause. Note that one can often remove that when used as a relative clause: That milk he used is sour. (See also, https://english.stackexchange.com/questions/104512/is-this-a-relative-pronoun-or-conjunction.)

  • 4th (last) That: That "that" that that guy used is ungrammatical. Here we can see the last that is again a determiner, indicating which guy is being talked about. We can also eliminate the 3rd that (the relative pronoun): That "that" that guy used is ungrammatical.

Note that, when spoken, the different that's are emphasized through varying volume and pauses. Here's an approximate description: (Normal) That (louder and lyrical like two syllables) THAT (very short, like it's connected to the next that as one word) that (normal but louder than the first that) that guy used is ungrammatical.

1. The Demonstrative determiners are also popularly called demonstrative adjectives. The latter nomenclature might have evolved as a mix of terms or a misnomer, but it's popular enough that it will likely remain in print (and on the Internet) for a long time. See https://english.stackexchange.com/questions/61456/use-of-determiners-as-adjectives/61470#61470 and http://www.lel.ed.ac.uk/~gpullum/grammar/detv_sli.pdf.

2. I've highlighted all instances of the relative pronoun 'that' with grey background so one can easily see where-it-is and where-it-isn't.

  • Someone may not conceive of this question, but it is a useful example and it helps sort out how these things work. It's also pretty interesting, I think :) – Mark Jul 13 '14 at 18:12
  • Awesome explanation, btw. I only take issue in saying the third "that" is a relative pronoun. A subordinating conjunction subordinates a clause to another clause, such as SINCE: "Since you've been gone, I can't stand the loneliness." But a relative clause ties a clause to a noun phrase: "I like the cake THAT Linda brought." Which CAKE? The cake THAT Linda brought. – Mark Jul 13 '14 at 18:18
  • @Mark, I've corrected #3 as per your comment. Thanks! – CoolHandLouis Jul 13 '14 at 19:37
  • Another good example is the substitutions in: This_1 thing_2 that_3 those_4 guys used was ungrammatical. (Credit to @F.E. for the basic wording, though I've enhanced it to make it clear.) – CoolHandLouis Jul 13 '14 at 21:07
  • @snailplane, thanks! I've updated the answer to reflect this. – CoolHandLouis Jul 13 '14 at 23:08

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