It's 1987 and thirteen year old Ramona Avery lives in Riverside, Massachusetts, the most boring town on the face of the earth. Thankfully she has her two best friends, Scott and Noreen, to make life worth living. All she needs is a boyfriend and her life will be complete. Too bad every guy who asks her out is a giant loser. Then she meets Lenny Sinclair, and Ramona is absolutely, positively sure that he is THE ONE. But when Lenny gets her pregnant, everything changes. He definitely isn't the guy she thought he was. Now Ramona has to deal with raising a baby on her own. No matter how hard she tries, though, she just seems to screw things up. Will she ever be able to straighten her life out?