Learn English – The usage of the word pretty is “pretty” confusing

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I am aware that there are plenty of threads on intensifiers(very, rather, pretty, quite, fairly, etc.), both on this site and on the web, because of their ambiguity in terms of meaning. What I have learned is that their meaning can change depending on which country you are from, which context they are used, or your intonation. So instead of comparing all intensifiers, I decided to make my question more specific. I chose to focus on the word pretty because of its "common" usage.

So as we can see, the word pretty has two meanings and unfortunately they are "pretty" opposite. My question is can you tell me, just by taking into account the example sentences below, in which sentences "pretty" means "fairly,", and in which it means "very?"

Does "Tom looks pretty tired" always mean "Tom looks a little/fairly tired" ?

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http://www.macmillandictionary.com/dictionary/british/pretty

Best Answer

It depends on intonation. With a certain, emphatic intonation, Tom looks pretty tired can mean "Tom looks very tired; indeed, his level of tiredness is remarkable." With ordinary intonation, it just means "Tom is moderately tired—tired enough to matter, but his level of tiredness is not especially remarkable."

The emphatic intonation that I have in mind drags out each syllable of pretty to an equally long length, about as long as the word tired. The pitches go something like E D C, like "Three blind mice". Of course, there are many other kinds of intonations and emphasis that a person could give the words, suggesting many different kinds of tiredness, and there is no precise, standardized code. You just improvise.

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