"How about this, you go on a date with me every day this week. If you still don't like me next Monday, then I'll let you go, but if you do end up liking me, then you'll be my girlfriend." Josh Hamilton is Riley Smith's best friend. They are both popular in school and on the baseball team. Josh has had a crush on Riley's twin sister, Olivia, for years. He finally finds the nerve to ask her out at a baseball game. Olivia is a nerd at school, not very popular. In middle school, she used to get bullied all the time so she isn't very confident. All of her friends are in relationships, but she has only ever been on two dates, both of them first dates. This is their story.

Christina is the most popular girl in the whole school. Everyone knows who she is. Guys want to date her. Girls want to be her. She is basically a mean girl in the making. But what will happen when history with the school nerd comes back to destroy her reputation as the glamorous jock-loving queen bee?