When we are writing, editing, or proofreading content it can be difficult to catch the nuances, which is a big reason errors creep in. And the problem has become even more pronounced as more and more people rely too heavily on the countless AI tools that are out there (instead of just reading carefully). All of these tools have one thing in common: They do not understand context.

This brings as to the unusual case of when the word “that” can be repeated. It isn’t as noticeable in conversational English, but when written some people (and almost all tools) will flag it as wrong.

Here’s an example of sentence that was flagged as an error in an article to be published in a journal:

Here we show that that does not generalize.

There are some cases where the repeated “that” can be wrong, but like so many issues in English, it depends on the context. The example above, however, is perfectly fine and grammatically correct.

Here’s a simple two-sentence example. 

The sky is blue.

The fact that that is true doesn’t mean it isn’t sometimes orange.

The second sentence is absolutely correct from a grammatical standpoint. The second “that” means this:

The fact that the sky is blue is true doesn’t mean it isn’t sometimes orange.

The second “that” replaces “the sky is blue” because repeating it isn’t necessary since it comes in the very next sentence. If the original fact being cited is in close proximity, what the writer/speaker is referring to is understood.

The important distinction here is that in this example the first “that” is a conjunction, while the second is a pronoun.

Let’s look at the second one first, as defined in Merriam-Webster’s Unabridged Dictionary. As always, the end of the quoted material is denoted by the box (∎):

1that

pronoun \ ˈt͟hat 

, t͟hət \ 

plural those \ ˈt͟hōz 

\ 

1a : the person, thing, or idea pointed to, mentioned, or understood from the situation : the one indicated 

<who is that>

<that is my father>

∎

So in our example, the fact that “the sky is blue” is indeed “the person, thing, or idea pointed to, mentioned, or understood from the situation.”

For the first one, here’s the edited definition from Merriam-Webster’s Unabridged Dictionary. I edited to stick with the relevant aspect:

3that

conjunction \ t͟hət 

, (¦)t͟hat 

\ 

1a(1) —used as a function word to introduce a subordinate clause that is a noun equivalent: 

<that many historic houses … are rapidly disappearing for lack of care has been emphasized by several organizations — Report: (Canadian) Royal Commission on National Development>

This repeated “that” is very common in conversational English. It looks funny when written, but can be correct.

When you hear a native speaker use it, the first “that” tends to be quick and the emphasis (shown bold) is placed on second “that,” like this:

The fact that that is true…

It’s mission critical to avoid reading sentences too quickly and then robotically assuming that something that initially “looks” funny is incorrect. The context is what determines whether it is correct.

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