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For writing a text book, I am looking for some ambiguous sentences with compound particles.

As an illustration, consider my attempt as follows. Recall that when の and に are combined, it results in a new particle のに, so there is a possibility to make ambiguous sentences with のに.

  • の can be used to nominalize clauses. For example: お酒を飲まないの
  • Nに can also be needed for some expressions. For example: アニメに興味がある

Now I have to find sentences with pattern XのにY such that they can be read in two ways:

  • Xのに、Y --> Even though X, Y
  • XのにY

タバコは吸わないのに興味がある。

It can be interpreted in 2 ways:

  • タバコを吸わないのに、興味がある。Even though I don't smoke, I am interested in smoking.
  • タバコを吸わないのに興味がある。I am interested in not smoking. (the speaker must be a smoker.)

Questions

Could you give me other better examples?

  • The object for 興味がある is missing if you use を instead of は after タバコ in the sentence meaning "even though I don't smoke, I'm interested in". Usually, 吸わないけれど or 吸わなくても is used in this case, not のに. – user4092 Jan 13 '17 at 7:32
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I came up with the following:

健気にも生きる人達。
健気に + も + 生きる / 健気 + にも + 生きる

それでは何も起こりません。
それでは / それ + で + は
(the former might seem uncommon but a GM of TRPG would say that)

それでも勝てる。
それ + で + も / それでも

Or I'm not sure whether this famous example is what you want though:

ここではきものを脱いでください。
ここ + で + はきもの / ここ + で + は + きもの

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