Meet Chad Stevens -- a 15-year-old boy existing in the small town of Holford. He’s a loner, a soloist -- until he meets fellow outcast Chris. Chris hates Holford and is planning his escape, and he enlists kindred spirit Chad to help.
When Chad faints in class after seeing a diagram of the female reproductive system, Chris makes it his mission to get Chad more comfortable with the old, bold, female form. The boys hear a rumor about an adult photo shoot outside of town and embark on a quest to find it.
When Chris gets knocked down the bleachers during an assembly by one of the school bullies, he cries out in pain for his mom -- earning him the humiliating nickname “Mommy.” Chad helps Chris plot to get a better nickname, until one of Chris‘ ideas threatens Chad’s relationship with school crush Sharla.
Because the previous Halloween was canceled due to extreme weather, Holford rescheduled the holiday for spring instead. Chad still wants to trick-or-treat, but Chris convinces him to go to a boy-girl party that goes horribly wrong. Meanwhile, Jay is on the run from Holford’s legendary maniacal bad boy, Johnny Slade.
Chad wrecks the family car and gets a job at Frost King to pay for the damage. Chad immediately clashes with manager Benjamin Brent, the only other male employee who sees Chad as an obstacle in his otherwise sweet life of being the only rooster in the hen house. Chad must endure Benjamin’s torture while Chris tries to raise enough money to set Chad free from the shackles of the corporate world.
Chad is smitten with new girl Destiny, but he blows his chance after saving Jay from a bully who turns out to be her brother. Chad enlists Chris’ help to win her back with an elaborate plan involving walkie-talkies and a mysterious aphrodisiac.
Chris is upset by how close his mom and her boyfriend Terry have become. When he sees Terry buying a ring at the flea market, Chris is terrified he’s going to propose. Chris and Chad concoct a plan to get Terry out of Chris’ life for good.
After botching his oral presentation for history class, Chad decides to make a movie instead. With Chris's help/interference, the project becomes increasingly off-topic and out of control, leading to a disaster of near-biblical proportions.
When Wayne declines Chad’s request to compete in Holford’s annual father-and-son Hexathalon, Chad asks Sharla’s dad to compete with him instead. Meanwhile, Joanie asks Chris and Terry to do the race together to strengthen their bond, and the contest brings out everyone’s true colors.
Chad’s classroom doodles draw the attention of the “cool kid” yearbook staff, who invite him to join their inner circle. Chad and Chris enjoy their popular status until Chad discovers their new friends have ulterior motives.