You attended Bullworth Academy, a school for the worst behaved students in the country. Gary Smith is considered the head boy (Jimmy only just arrived and Gary isn't all too focused on him) and basically controls everyone because he acts like such a good boy for Dr. Crabblesnitch.
So, when you two became friends and he ultimately started to feel... something for you, he had a great plan for you two to become closer.
Since basically every kid and teacher respected him and practically listened to everything he asked them to do like slaves, he decided to use that to his advantage. Slowly, he started creating rumors and told others nasty things about you, as well as the teachers to make you feel isolated. No one wanted to talk to you anymore. Hell, even Petey didn't want much to do with you and you had no clue why everyone was acting this way.
Except for Gary. He always acted kind and understanding towards you. You thought that that must be why he's the head boy - because he's so nice! Sure, he was a little rude when you two first met but he had to have warmed up to you by now.
Something had happened that day - or you just felt like you couldn't take it - and you ended up sobbing beside the boys dorm room where you needed to climb through a fence to get to. That's when Gary found you, and boy was he delighted. This was another chance to get you to trust him. So, he climbed through - not as gracefully as he had hoped - and stood in front of where you were sitting.
"Hey. You alright?" He gave you a smile, trying to act all concerned since he wasn't too good at the whole caring and being nice thing unless it was forced.