4 Books Found

Based on your description:

"A story about a kid with red hair either going to a new school or entering a new grade. He is nerdy and totally reinvents himself to be seen as cool. I think he had red hair that he seriously gels down to make straight, gets contact lenses, maybe even starts wearing a leather jacket. He ends up getting a girlfriend, or kisses a girl at the very least. I remember that the book's first scene is him being driven to school by his mom and it's mentioned that the oatmeal he had for breakfast is being felt in his stomach. I think the kiss occurs in gym class or recess? They were on scooters or sleds or something, and fell."