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I was talking to my language partner and she mentioned ぶさかわ being used in situations when you want to describe something not pretty but nice. Apparently the word is relatively new and was first used in a pet magazine.

What is the actual meaning?

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Probably, it is short for [不]{ぶ}[細]{さい}[工]{く} 'ugly' + [可]{か}[愛]{わい}い 'pretty'.

It may sound contradictory, but the direction of the two properties point to slightly different angles, and the positive one somehow out wins the negative property.

Realizing that you mention it was used in a pet magazine, I think it typically refers to the face of a bulldog or a pug, which sometimes is ugly but nevertheless cute. It is contrasted with other kinds of dogs that have the nose sticking out and the chin skinny, which are considered simply "handsome/beautiful".

A similar one with contradictory flavor is ヘタウマ, which is short for [下手]{へた}([糞]{くそ}) 'bad at' + [上手]{うま}い 'good at', and means 'drawings or writings intentionally made to look bad (like a child's scribble) but are pretty much under control'.

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Yeah, that's what I thought but I was hoping for a more exciting origin. –  Oleg Levy Jun 17 '12 at 13:17
    
One thing to note is that, 不細工 is pretty much Kansai (or other) dialect. It is not used much in Tokyo. In Tokyo, the word ブス 'ugly girl' and ブ男 'ugly boy' are more common, so the counterpart will more likely be ブスかわ. –  user458 Jun 17 '12 at 13:23

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