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Both Google Translate and Spanishdict.com translate silly as tonto. However, both as translate dumb as tonto also. I find this hard to understand because silly and dumb are not synonymous in English, and notably calling someone silly in English is generally fun and playful, whereas calling someone dumb in English is an insult.

How should I understand this? Is it completely context-driven? Is there a safer word for silly for a novice to use to ensure it is not taken offensively?

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    It always depends on the context... but in general, do not say tonto to someone until you know him/her well. – fedorqui Aug 22 '16 at 14:39
  • It is exactly the same as calling someone "fool". Sometimes is offensive and sometimes it is not. – DGaleano Aug 23 '16 at 14:29
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It actually depends on the context, and also depends on intonation a lot. However, I think most of the times we use it (in Spain) in an offensive way, it comes always with some emphasize that makes clear we're talking seriously. If you say it laughing in a non so-serious context it is difficult to offend someone or get misunderstood.

Here in Spain you could use 'bobo' as a translation for silly, since 'bobo' is even more playful. However, it can be offensive too, like you can see here and here, but is really not so common.

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