ANSWERS: 4
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In my own POV, being transparent is tantamount to not being able to keep secrets. That is a bad thing, especially when it's a top-secret stuff you're entrusted with.
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The negative connotations are: Being able to see through something or someone. Nothing between the ears, only light passing through. Usually meaning a person who lacks character. Being able to see through a lie to view deception. A shallow person. No subtlety. Thin-skinned.
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I don't see that the word should have any negative connotation at all, unless you mean that a person who is trying either to deceive or to appear clever/witty/intelligent/educated/refined/whatever, is not succeeding at it because you can see right through their attempt to deceive or impress. Even that is not negative, really, just perceptive LOL
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Some one tries to be something they are not is transparent to some one who sees through their disguise. Some people would call them a phony-- this is the negative.
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