She might have been the most infuriating girl on the whole campus, but he'd be damned if he didn't both envy and feel deeply sorry for her at the same time. Rachel Berry was probably the person who could understand him the most in that hell-hole they both lived in.
Kurt may have been one of the more quiet students, at least verbally. His outfits tended to be the loudest among the men and the women, but he supposed it balanced out. But he was smarter than people gave him credit for, which is in part why he spent more time observing and less time acting. It's why he slipped into the background a good amount of the time. Being the star of the show had consequences that he watched play out every single day. Still, he watched people be loud and proud, but none of it was real. They were all actors and actresses, like high school was just one big show.
Life is a stage. Some people have every single person watching with rose colored glasses from the audience. They've got people who will support them even if they hit the wrong note and fall on their faces, and they damn well know it. These people were popular, and they tended to not care about giving their best. Whatever entertained the masses.
Occasionally someone is unabashedly just themselves, but the best they can be. They know who they are, they know what they want, and they're not looking at the audience. They don't have a single person in that audience rooting for them. People rooting for the other members on stage aren't this secure, and neither are the people they're cheering for. They throw things, and shout obscenities. They're abusive, and they turn the spotlight off of that person, but nonetheless they perform because the performance isn't for them. Rachel Berry was this person.
Kurt can't afford to be Rachel, no matter how much it sets him on fire to see her doing what he loves. To see her striving for her dreams that are so achingly similar to his own. She's so similar to him, but no one would know. Deep down he's afraid, so he stays in the background always watching.
