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I think this is a question I should have asked a long time ago.. What is the
difference between 案外 and 意外? What does the correct situation look like when
using either?

Example with 案外:

> 人生は **案外** 短いものです。ですから、こんなにも貴重な人生を、自分が満足できない仕事で無駄にしているなんて、驚くべきことです。

Example with 意外:

> **意外** なことに、とてもうまくいってます。

The English translation definitely didn't help me with this one, as both are
"unexpectedly". Is there a certain degree that is associated with each?
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2012-07-24T14:35:48.017
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word-choice
When is the correct situation to use 案外 or 意外?
* 意外 "unexpectedly"
  * 案外 "after all", "unexpectedly in such a way that something is inferior than it was originally thought"

> 人生は案外短いものです。  
>  Implication: Life is thought to be long.

In your examples, they can be switched with some adjustment in the form.

> 人生は意外に短いものです。  
>  案外、うまく行っています。  
>  Implication: People thought it would be more difficult than it turned out
> to be.
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2012-07-24T16:35:51.283
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I've always thought of them in terms of their kanji make-up.

  * [`案`](http://jisho.org/kanji/details/%E6%A1%88): can mean "plan/expectation"
  * [`意`](http://jisho.org/kanji/details/%E6%84%8F): can mean "idea/mind/thought" (with the thought process maybe implying some subjectivity)

From there:

  * [`案外`](http://kotobank.jp/word/%E6%A1%88%E5%A4%96?dic=daijirin&oid=DJR_anngai_-010): 

>     * "not according to plans/expectations"
>     * "[contrary to/against] expectations"
>     * often, but not always "disappointing(ly)"

  * [`意外（に・と）`](http://kotobank.jp/word/%E6%84%8F%E5%A4%96?dic=daijisen&oid=00738200):

>     * "[against/not] what was [thought/expected]"/"(I/you) wouldn't have
> thought"
>     * "surprising(ly)"

Daijisen has some usage notes differentiating the two in the definition for
[`案外`](http://kotobank.jp/word/%E6%A1%88%E5%A4%96?dic=daijirin&oid=DJR_anngai_-010).
I think it basically says:

  * `案外` is used when expectations/situations turn out different:

> 期待していたが、案外つまらない映画だった  
>  I had [expectations/hopes], but it was a disappointingly boring movie.
>
> 心配していたが、仕事は案外楽だった  
>  I was worrying, but contrary to expectations, the job was easy.

  * `意外な`/`意外に` are used when the reality is different to what was thought, or with things that can't be expected:

> 意外に時間が早くたってしまった  
>  Time passed surprisingly quickly.
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2012-07-24T22:09:03.483
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「 **意外** 」 is used when what you're describing is unexpected.

「 **案外** 」 is used when what you're describing is **_contrary_** to what you
expected and is most frequently used with adjectives.

```

    「案外安い」 OK
    「案外簡単」 OK
    
```

However, I don't believe that you can say 「案外に」 the way that you would say
「意外に」

```

    「案外に安い」 NG　⇒　「意外に安い」 OK
    「案外に簡単」 NG　⇒　「意外に簡単」 OK
    
```
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