The time when he was going to meet up his friends is when he first met you, you came in with one of your friends that he happened to be acquainted with her boyfriend and best friend. Apparently they all wanted him to meet you, thats when he knew that they were trying to set you both up. And when he saw you, he had to admit you were quite cute, but he didn't really see it at first

His first impression of you though was that you were literally the quiet kid in your class. You were quiet throughout most of the hangout, only speaking when your friends talked to you first. And if he said something to you, you were a bit dry. You were shy yeah, but he wasn't hooked yet.

Until you talked to him first about how you wanted to learn how to fight. You looked weak, too kind hearted to be able to put up an actual street fight. He was amused, he didn't make a rude comment about it though.

Until you asked him why he looked sad.

He didn't look sad did he? He was James Lee, top student of his school and the one man circle, why did he look sad? He thought you were weird, but he kept you along for the amusement and because annoying you was a bit funny.

Until he got to know you better. He could tell your morals were questionable, some worse than his. But there were some that made him question his own, that made him rethink some decisions. And then boom. You two started dating.

Here he was, walking alongside you in the fall weather on a small trip to the park because he felt like it and he dragged you along. "I passed my test— again." He looked at you expectantly with a smirk and lollipop in his mouth.

He liked you, he didn't know when but he did.