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Recently I wanted to bitch at my staff and I wrote the following sentence:

Do you want someone who has taken off their shoes to prepare your drink without washing their hands?

And then it suddenly felt weird to me because, technically, the to-part could refer to the relative clause as well as the nesting main sentence. The context makes it clear here but still I was confused at the second reading. I thought about using a comma but then I remembered that necessary relatives are not to be "comma"-ed (my native language is German). Here are my questions:

  • Is the sentence proper English?
  • If yes, am I correct that it has a potential double meaning?
  • If yes, is it considered bad style or would people just rely on context?

Last but not least:

  • How could that be phrased in a way that avoids the issue?

As for the context... taking off your street shoes to put on work shoes means you touch the shoes. Some people go and do a caipirinha right after that without washing their hands

  • I kind of like the very slight possibility of confusion that could give rise to the interesting image of preparing drinks barefooted, but you could also consider the following if you really want to avoid it: "Would you want someone who has not washed their hands since changing their shoes be the one [responsible for] preparing your drink?" – Papa Poule May 4 '15 at 22:48
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Yes, the sentence is perfectly proper English.

It is possible to construe two different meanings from the sentence, yes; but the second meaning is extremely unlikely. I had to read the sentence four times after reading your question before I realised what the second interpretation would be. It would be a very strange question to ask. (It’s already a bit odd as it is—what does not wearing shoes have to do with making drinks?)

In fact, there are at least four possible ways you could construe this question—each more unlikely than the next.

It is only ‘bad style’ (if you can even call it that) to use structures that are highly ambiguous and remain so even in context; this is definitely not that. Even without context, the risk of ambiguity is so small here that there is no need whatsoever to worry.

Basically, the options I can think of are:

Do you want [someone who has taken off their shoes] [to prepare your drink without washing their hands]?

= If someone is going to prepare your drinks without washing their hands, do you want it to be someone who has taken off their shoes?

Do you want [someone who has taken off their shoes] [to prepare your drink] [without washing their hands]?

= If you’re not going to wash the hands of the person who’s preparing your drink, would you want them to have taken off their shoes? (Bizarre question.)

Do you want [someone who has taken off their shoes to prepare your drink] [without washing their hands]?

= If there is someone who has taken off their shoes in order to prepare your drink, do you want them without washing their hands? (Utterly grotesque question.)

Do you want [someone who has taken off their shoes [to prepare your drink without washing their hands]]?

= If there is someone who has taken off their shoes in order to prepare your drink with dirty hands, do you want them? (Downright outré question.)

— And I’m sure you could think of even more mind-boggling ways of interpreting the question.

The point is: everything is ambiguous. Every single sentence you utter in a day can possibly be misconstrued to mean something else than what you intended for it to mean. This is very rarely a problem, however, because people don’t usually spend their time trying to find obscure and bizarre meanings in what other people are saying to them—they don’t have the time, because the conversation has already moved on and they need to come up with an answer as well.

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    Thanks. I know that stuff is ambiguous. I was just wondering if it is something similar to dangling participle or some of that other stuff that English grammar has to offer. As for the context... taking off your street shoes to put on work shoes means you touch the shoes. Some people go and do a caipiriha right after that without washing their hands. – Emanuel May 4 '15 at 18:59
  • Oh, I see—it was the actual removal of the shoes, rather than not wearing shoes, that was relevant. To get rid of that bit of ambiguity, I’d probably be more specific and say, “Would you want someone who’d just been touching their outdoor shoes to be preparing drinks for you without even washing their hands?” or maybe “Would you want someone to be making drinks for you without even washing their hands first if they’d just had their hands on their outdoor shoes?”. – Janus Bahs Jacquet May 4 '15 at 19:02
  • @Emanuel I think your listeners would readily understand the context. However, like Janus I was a little confused; I thought it was a slightly weird but very effective remonstrance. Perhaps you could edit your question and add your comment as a footnote. – Mari-Lou A May 4 '15 at 19:27

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