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They can both mean troubled or worried, based on my reading of Google Translate. But are there subtle differences in usage or context between them?

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No, actually, as fas as i know, preocupado means "worried or troubled" and molestado means "upset" or "bothered" – Laura Sep 27 '12 at 13:50
Just as a little correction, the word "molestado" is wrong as an adjetive, the correct one is "molesto". "molestado" is the past participle form of the verb "molestar". – Dante Sep 27 '12 at 16:11
@Dante: Fixed the spelling. – Tom Au Sep 27 '12 at 20:02
@TomAu Maybe you are confused about the using of "no te molestes" and "no te preocupes"? – Laura Sep 28 '12 at 8:09
@Laura: Yes, that is one context where they seem to be used similarly. – Tom Au Sep 28 '12 at 19:27
up vote 6 down vote accepted

You seem to have some sort of confusion here.

"Preocupar" means:

  1. To trouble,
  2. To worry,
  3. To be concerned.

"Molestar" literally means:

  1. To bother
  2. To make upset
  3. To hassle

"Molestado" needs some elaboration particularly in its use. It is gramatically incorrect to say "estoy molestado"; you say "estoy molesto" ("I'm annoyed" or "I'm pissed") or "estoy preocupado" ("I'm worried", "I'm troubled").

In the context of having someone make you upset, you would rather say "me han molestado" or "he sido molestado" which both mean more or less "somebody has hassled me" or "I have been disturbed" or even "somebody made me upset" or "I have been bothered".

Maybe if you could give a little more context into why you think both terms mean troubled or worried you could get a better answer.

Hope this helps.

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