"a superficially charming person who is indifferent to the pain of others and has spent his life in and out of prison for violent crimes would most likely be diagnosed with which type of personality disorder? "

Can be diagnosed with an antisocial personality disorder. In this personality disorder, the person cannot adapt socially or follow social or legal norms, is characterized by constantly lying, breaking the law, impulsive behavior, and little or no empathy. Its diagnosis can be from childhood, but it is usually diagnosed in adolescence or early adulthood.

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