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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?
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.
En Perú sería una ofensa traducirlo "tonto". Más bien decimos "disforzado" lo cual se aplica a alguien quien se hace el payaso o está haciendo reír a alguien.
