When he was little, Rory's best friend was Georgie Denbrough; it was kinda perfect, considering their big brothers were the same age, so there was always a reason for them to be around each other. And unlike Georgie, who was a smiley, chatty boy, Rory was shy and had a harder time making friends. When he was in first grade, his best friend went missing, and he was suddenly all alone--aside from his big brother, of course. 

Eventually, they moved away from Derry, and for a long time, Rory really didn't talk to anyone besides Richie. It took months before he finally started making new friends at school. As he got older, Rory slowly started to grow out of his shyness (though it wasn't until college that he started truly coming out of his shell). When he was 14, he got into an accident while messing around with some friends, and ended up losing his right eye. He was insecure about it at first, but Richie (in all his infinite wisdom) suggested he have fun with it, find a way to laugh at it before anyone else could. So that's what Rory did. He made up all kinds of ridiculous stories for what happened, made the pirate joke before anyone else could whenever he wore an eyepatch, and started collecting fun fake eyes. 

Rory started having dizzy spells after the accident, but it didn't become a real issue until college. He would pass out at school seemingly at random and got frequent headaches. He dropped out of school and moved back in with his parents while going to various doctors to figure out what was wrong with him. During that, when he felt the most isolated, Rory started making silly videos of himself commentating on whatever show he was watching or book he was reading, and posting them online. He didn't really expect anything to come from it, he just. . .needed something to do. Before he knew it, he had a bit of a following. For some reason, people enjoyed what he had to say. By his late 20s, he was something of an Internet celebrity.