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Does the 目 mean 'eye' in this case? What does Au mean in this case? The pain and the 目 coming together to experience the hurt?

Is this a one-off sentence or can I use other variations like 苦しい目にあう (only negative ones?) or 楽しい目にあう?

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「目{め}」 has far more meanings than J-learners tend to think. A decent dictionary would give over ten.

Does the 目 mean 'eye' in this case?

No, it does not. 「目」 here means "experience", so 「痛{いた}い目」 means a "bitter experience".

What does Au mean in this case?

「あう」 used in this expression means "to encounter", "to go through", etc.

So, "to get a black eye" is not what this expression means at all. That is unless getting a black eye was coincidentally the end result from your bad experience.

Is this a one-off sentence?

No, it is not.

「苦{くる}しい目にあう」 is just perfect.

「楽{たの}しい目にあう」 would be less common but still okay.

The adjectives that are used often in 「~~目にあう」 are:

ひどい、散々{さんざん}な、危険{きけん}な、つらい、悲惨{ひさん}な, etc.

It would mostly be a word with a negative meaning. I think it is safe to say that 「痛{いた}い」 would be the most common adjective.

The expression that I personally would suggest that J-learners learn would be 「いい目を見{み}る」, which means "to be fortunate/lucky". I say this because I almost never see a J-learner use that expression.

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    I appreciate the notes on expressions not frequently used by learners of Japanese. It helps to grow a much more native perspective on the language rather than purely grammatical and formulaic. – Joshua Detwiler Sep 28 '17 at 5:24
  • Thank you! Was wondering if it might not mean 'hurt eye' but maybe literally it means that as the originator of the proverb. Interesting. Guess it was just a coincidence. Good mmemonic for myself though Would certainly keep いい目を見みる in mind. Short and easy to remember too! I suppose 目 can be considered an alternative to koto for the same cases as well right? ひぢい目になっちゃった&ひどい事になっちゃった seem fine。 – shoryuu Sep 28 '17 at 11:01

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