regional.cl.lexicon
Everyday Chilean words: cachái, weón, bacán, pololo, fome
A survival kit of chilenismos: cachái (get it?), weón/hueón (dude/idiot), bacán (awesome), fome (boring), pololo/a (boyfriend/girlfriend), la raja (great), cuático (intense/weird), al tiro (right away).
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Explanation
The keystone is weón (written hueón/güeón, from huevón). Like Argentine boludo it swings from insult to affectionate 'dude' purely on tone: ese weón (that guy), no seai weón (don't be an idiot), weón, ¿cómo estai? (dude, how are you?). It also works as a filler.
Judgments: bacán and la raja and filete mean 'great/awesome'; fome means 'boring/lame'; cuático means 'intense, over-the-top, or weird'; penca is 'crummy'. People and life: pololo/a is a steady boyfriend/girlfriend (pololear = to date), cabro/a chico is a little kid, la once is the evening tea-meal, and carrete is a party (carretear = to party).
Time and manner: al tiro means 'right away', altiro nomás 'right now', and la raja / bacán double as enthusiastic yes. Cachái ('you get it?') punctuates nearly every sentence. A dozen of these plus po and the voseo verb forms and you sound recognizably Chilean.
Examples
Hey dude, you know about Saturday's party? It's gonna be awesome.
Region: CL
That movie was really boring.
Region: CL
I'll be there right away, wait for me at the corner with your girlfriend.
Region: CL