I’m a computational linguist. You could say that what my job is all about is dealing with ambiguity. If there were no ambiguity in language, computers would be able to understand it. But, language is full of ambiguity. If I say “what we need is more intelligent waiters,” does that mean that we need more waiters that are intelligent, or waiters that are more intelligent? Either meaning is possible–it’s ambiguous. If you read “lead,” is that the verb, or the metal? Either is possible–it’s ambiguous. In fact, you will hear and read very little today that is not ambiguous in some way.
The Zipf’s Law connection: today I had blackberries with my breakfast. I didn’t know the word for that in French. It turns out that the word for blackberry in French is la mure. In fact, there are three words that are pronounced exactly the same:
- la mûre: blackberry
- le mur: wall
- mûr: ripe, mature
That’s just the roots, though. All of these words have plurals (for the nouns and the adjective), and the adjective has male and female forms, too. So, you have:
- mûre blackberry
- mûres blackberries
- mur wall
- murs walls
- mûr ripe, mature (male singular)
- mûrs ripe, mature (male plural)
- mûre ripe, mature (female singular)
- mûres ripe, mature (female plural)
Note that mûre “blackberry” and mûre “ripe, mature (female singular)” are spelt the same, and mûres “blackberries” and mûres “ripe, mature (female plural)” are spelt the same. Here’s the kicker: every single one of the words listed in this blog post is pronounced the same!
So, now that you know all this, you’ll understand this story: one fine summer day, I went to the fruit stand up the street. I asked the marchande for some figs. She asked me if I wanted wall figs. Wall figs, I wondered to myself? What the hell are those? I looked at her with that dumb look that I’m giving everyone in France 50% of the time due to my inability to understand the simplest sentences. She tried again: Are you going to eat them today? Do you see where I had resolved an ambiguity incorrectly?
Zipf's Law 
great example and nice picture – j’adore les mures! (avec un accent circonflexe I can’t reach here). But English has masses of ambiguities, and as I tell my students, to try to understand a word you always have to work on the context and shouldn’t refer to a dictionary 🙂 could it be that your 50% would decrease if you just concentrated on whole sentences and not separate words?
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Yes, absolutely—English has rampant ambiguity. Ambiguity is actually one of the defining features of human language. In contrast, a well-designed computer language has no ambiguity. Context is the hottest thing in my field today–in computational linguistics, we very rarely use dictionaries, and the most popular approach right now takes advantage of efficient encodings of all of the contexts in which a word can occur.
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