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On occasion, I end up writing sentences that contain a duplicate word, often what is probably a preposition (or better yet, an adposition). The specific example that I just ran into involves a duplicate 'to' in this sentence:

I think we really ought to leave that up to the people we're assigning the label to to judge.

Is this proper grammar? If it is so technically, is it proper style to leave it like that, or should it be rephrased, so one doesn't stumble over it when reading?

Should there be a comma between the two?

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While your sentence

I think we really ought to leave that up to the people we're assigning the label to to judge.

is not grammatically incorrect, it would be considered inelegant by many writers, especially because it involves a duplicate preposition. (It is not uncommon to find "...had had..." in formal contexts and this is not usually frowned upon.) So, you are right your construction is not stylistically preferred. Also, there should not be a comma between the duplicates.

Here are possible revisions in increasing order of elegance:

  • I think we really ought to leave that up to the people to which we're assigning the label to judge.

  • I think we really ought to leave that judgment up to the people to which we're assigning the label.

  • I think we really ought to leave that judgment up to the people whom we're labeling.

  • I think we really ought to leave that up to the people we're labeling to judge.

  • I think we really ought to leave that judgment up to the people we're labeling.

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    Quick tip, Jimi, I recommend using the angular right bracket to quote lines here, rather than the 4 space code indentation, as the latter switches over to a fixed width font. angular brackets provides for a batter rendering style too. Dec 22, 2010 at 6:32
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    +1 especially for your last sentence. (I'd even revise "I think we really ought to" to "We ought to", if it were up to me.) Dec 22, 2010 at 6:40
  • @Joost Schuur: Thanks for the suggestion. I usually reserve the blockquote environment for actual quotes from the question (like I did for yours) or referenced sources, while I use the pre (code) environment for my own examples. Certainly doesn't look so nice, so I'll consider implementing your suggestion in future posts.
    – Jimi Oke
    Dec 22, 2010 at 6:59
  • @ShreevatsaR: Thanks. Completely agree. Thought of excising "really" in the final example, as well, but I'll leave that to the author to decide.
    – Jimi Oke
    Dec 22, 2010 at 7:01
  • @Joost Schuur: I've been implementing your suggestion regarding my answer formatting, and the results have been wonderful! Thanks!
    – Jimi Oke
    Dec 23, 2010 at 17:43
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I have seen duplicate words in print frequently, but usually with words like "had" rather than "to". For example: "If Joe had had a better instructor, he would have passed the test." Such sentences can be a little hard to read, but in general there is no rule against it; the construct is grammatical. Often a reader will have the same reaction as an automatic spell checker -- "This must be a typo" -- only to re-read and see that it actually does make sense.

There seems to be a case for the notion that "had had" is more acceptable than "to to". In print, it's probably best to avoid "to to", but when spoken, I really don't see a difference regarding the level of awkwardness or clarity. For example:

Person A: I'm really not in the mood to run the mile right now.

Person B: But you have to to make the team!

Spoken with proper tone of voice, I think this usage is perfectly acceptable and understandable.

In general, I would consider rewording the sentence to make it flow better, on a case-by-case basis. Here is an article provided by Grammar Girl discussing usage and correctness in more detail.

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    "Had had" is not a duplicate preposition; it's just the past perfect of "have", like "had eaten" and "had gone". So I think it's unrelated to the question -- for instance, you cannot avoid "had had" by reordering the words as you can do here. Dec 22, 2010 at 6:35
  • @ShreevatsaR: Yes, you are right. I was describing a larger class of duplicate words, forgetting that the OP specified adpositions. I will edit my answer accordingly. As a reader, though, I still find that "had had" has a similar awkwardness to "to to", so I think it's related. (Like how I did a triple "to"? :) Dec 22, 2010 at 9:38
  • Great link to the Grammar Girl article, Mitch. Dec 22, 2010 at 13:26

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