Stewie Griffin goes to high school in "McStroke" episode eight of season six of Family Guy. It first aired in the United States in January 2008 and is also the episode where Peter gets a stroke from eating too many free burgers.
Stewie makes a bet with Brian to enroll in high school and become the most popular boy in a week.
Stewie chooses the name "Zach Sawyer" and starts getting in with the cool crowd immediately and easily wins the bet. The coolest girl, Connie Damico, wants to "go to Anal Point" with him and of course he obliges.
When they get there and Stewie takes off his pants she laughs and leaves him there for his "baby penis". The next day he is teased at school and he decides to get revenge on Connie.
She agrees to give him one last kiss but when she closes her eyes Stewie takes off all his clothes so everyone can see that he really is a baby. Connie is arrested and Stewie is satisfied.
Cool facts about this episode
* It is one of the episode that did not include Seth McFarlene on post-production because he was participating in the Writer Guild of America strike.
* It was named the Worst TV Show for the Week by the Parents Television Council on January 25, 2008.