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Now, that's where role-playing comes into play.

Sure, you might be able to roll high, with high modifiers, but what you say could affect the DC. Talking nice to someone, say, a Captain of the Guards, in order to get their help, means that you might only need a 10 to pass, and if you talk real nice, even getting a total of 5 when trying to roll with advantage might be good enough - but, insult their mother - you'd best roll a 20, at disadvantage, to keep them from calling the guards, and the local thieves thieves guild (whose leader is the guard captain's brother), who will then join forces to defend the honor of said mother.

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