Cindy centers around two misfit middle school cheerleaders, Cindy and Heather. They both desperately want to be more experienced with boys and dating, but neither really have any idea what they're doing. Heather thinks she has everything all figured out after a 'date' with a boy from school which leaves Cindy trying desperately to catch up. After a romantic encounter with the boy she likes, Heather and the rest of the cheer squad convince Cindy that the consequences of her actions are far more severe than she could have imagined.