The shady guy at school should be involved with the story of the woman in the pharmacy. At the very beginning, when you try to find out about anal, she wont talk to you about it but your friend at school then tells you, that the shady guy sells pills that will help you, which you then put into her drink during her coffee break. So, it is not Adriana who sends you to him, but the guy at school.i am having an issue with the shady guy at the school I cannot trigger him. I am very far into the game and usually he is triggered by now. I have great points with Adriana (studio girl) and I have progressed with her very far she talks about him but never sends me to him as she did in earlier versions.