Oh, I think I get then problem here. This isn't an ordinary CS: it's can application. In that sense, Milo would be answering the questions, not you. SO he couldn't have met Kyler yet. In addition, I don't get a feel that your character is speaking tio me in the sense all accepted characters are. I want to get to know your character. Also one of your sentences should be rephrased along the lines of; "Milo had nothing much better to do with himself; if he's going to do something why not make it for the good of everyone?"
High casual would require most sentences to be clear and concise. And remove it, for the sake of it being irrelevant.