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When I was talking to my girlfriend, she mentioned an incident where one of her friends surprised her with a gift. She said something like that least unexpected ... after which we got into a debate that least expected is right rather than least unexpected.

I said that least unexpected would be more like expected. After this, I googled the phrase and to my surprise found that least unexpected is used to express something that was not expected in many places. For instance, this:

“A Gem in the least unexpected place”

So I'm a bit confused now. Which one is right?

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Can you include some of the phrases you found where least unexpected is used to mean something that was not expected. It seems like it is being used wrong. – Urbycoz Jan 2 '13 at 11:12
@Urbycoz I found googling them, ex: "A Gem in the least unexpected " – Net_R Jan 2 '13 at 12:04
Can you post the link, so we can have more context. – Urbycoz Jan 2 '13 at 13:06
Welcome to ELU. I have taken the liberty of incorporating your Google finding into your question; around here it's regarded as a courtesy to answerers to provide this sort of information in the question, to save them the trouble of looking it up for themselves. – StoneyB Jan 2 '13 at 21:18

Least expected refers to something that is the least likely (or most unlikely) to happen. Least unexpected refers to something that is the least unlikely (or most likely) to happen. Using one for the other is simply a mistake.

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Least unexpected may in some contexts be the phrase called for. These, for instance, from the first page of Google results on “least unexpected”:

The Least! Unexpected! News! Story . . . !Evah source

The least unexpected award of the night – Meryl Streep gets her gong for The Iron Lady. source

Nobody was surprised that Tom Cruise was divorced and Meryl Streep won the Golden Globe; everybody expected these events, so neither story was at all unexpected. It is only a modest hyperbole to describe these as least unexpected.

On the other hand, this review (also from Google first-page results) clearly has it wrong:

“A Gem in the least unexpected place” ... We were on our way to Grand Tetons and had a long day of driving. We were both thinking lets just find a local "greasy spoon" and check it out ... source

In conversation, or in quick, casual writing, people use the words that occur to them on the spot. Unlikely or unexpected, get jumbled up with least likely, least expected, and the result is least unexpected. Nobody rewrites, nobody's keeping score, both speakers/writers and hearers/readers understand what is meant, so there's no harm done. Such misuses are not in the least unexpected.

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