Holly's new, young teacher has a dark past, and a dangerous future. She soon finds herself charmed by his ways, and gets thrown into the chaos. Who knew having an ex-gangster for a teacher could be so troublesome? As Holly and Mr. Heywood grow closer, more questions about his past come upon Holly, as does danger. What is Mr. Heywood keeping from Holly? And why is it so bad? But most importantly, if she falls for him, could their relationship survive? After all... it would be a proscriptive relationship.

<<Previously; I'm In Love With My Best Friend...Did I Mention He's Gay>> There's only one guy that has never showed any interest in Emi Aldridge, Matthew Fletcher, her best friend. Of course, it's completely too common that she's in love with him, but hey, the heart wants what the heart wants. When Matt tells Emi he's gay, she's totally crushed, but as his best friend, she has to support him and is doing everything she can to help keep his secret and save his reputation, even if it means losing hers...

Gracie May Howards is a brat. She's mean, and she not very smart at all. But she has that personality that's strong that you can't say no to. She is rather naive when it comes to guys. She really doesn't know anything about love, about accomplishments, and feeling good about what you do, until she meets her arrogant, rude, straight forward, mean Tutor.

Josh is your steryotypical hot guy with charm, chicks on his arm, and an ego to cover up his true personality and feelings. Jenna is not your typical teenage girl. She has mild OCD, a crazy family, and a need to prove her mother wrong. Jenna and Josh had completely different lives until Josh's parents decide to force a life change on him by sending him to an all-girls boarding school. Jenna's school.