Today was the graduation / term end ceremony at elementary schools across Japan. A class of fourth graders who I’ve taught for the past three years made me a book of notes. My favorite comment so far is the following, from one of my favorite little kids who is a legendary banana thief:

「ダニエル先生は、せが高くていいけど、小さいところに、はいれなくてかわいそうですね。」

かわいそう is a phrase that I remember hearing for a long, long time before I ever really got a sense of what it meant. I remember thinking, Is this person really saying that person is cute? Well, clearly that’s not what it means.  (For any kanji students taking notes: かわいい = 可愛い ; かわいそう = 可哀想 or 可哀相; and, yes, you actually see shit like that in shosetsu).

It’s a difficult phrase to translate into English, and it often ends up as words like pathetic, piteous, miserable, or wretched, all of which seem far to harsh. This is a situation where it’s useful to consult a Japanese dictionary and check the definition in Japanese.
    
That gives us:

弱い立場や逆境に在る者に対して、出来るなら何とか救ってやりたいと思う様子。

I’ll tell you right away, I have no idea what 逆境 means (although I did know the pronunciation – ぎゃっきょう), but it doesn’t really matter – the basic meaning comes through. It is being in the state of feeling as though you want to help someone in a weak or 逆境 position if possible.

Now, rather than finding a specific word to translate it into, what would you say in English if you were feeling like that and decided to vocalize these feelings? I can think of at least one:

“Aww…that poor little puppy.”

“Poor” would be listed as one of the possible translations, but I think the tone of the sentence would better express the meaning of かわいそう – a tone that would express sympathy and an honest desire to help the puppy. And I’m not referring to the tone of this sentence if it were being said by a person in the military about to throw the puppy off a cliff. That would most definitely not be かわいそう. That would be pathetic and miserable.

So this sentence really means something like this:

“It’s great that Daniel-sensei is tall, but it’s too bad he can’t fit into small places.”

かわいそう is a great way to express true sympathy for something you feel for. It definitely has a bit of wabi-sabi wrapped up into it, which makes it even more expressive. Plus, it’s hilarious that I can’t fit into small spaces.