Sophie Bennett is Jackson High school's match maker or as she is more commonly called Cupid's assistant. She is the type of girl that you go to to ask for relationship advice. She has a great judge of character, she has a talent for getting two people together. Or so everyone including herself thought. What happens to her judgment when she is having family problems, such as her cheating mother. Her best friend Simon and her younger sister Hannah seem to be ignoring her and always around each other. Is something going on there? Also what happens when Simon and a few of her friends are pressuring her to sing and tryout for the school musical, but she has horrible mental scars from singing because when she was younger she wasn't a good singer and everyone even the closest people to her made sure she knew it by saying it rudely. What also happens when an extremely hot new boy comes to school and he is interested in Sophie! While she is dealing with all of this she has 2 Cupid's assistant jobs. One is to set up one of her friends Mary with a cute cross country boy Peter. But it's getting hard because they keep hurting each of and the schools ass hole Tanner wants to make sure that never happens. The second one is to get Courtney and Kevin together, which seems easy but is actually harder than it looks.