Meanwhile, Dorrit is sitting on a couch, smoking a joint, talking to her kissing boy about books like 1984. His name is Miller? No, scratch that, his name is irrelevant. Dorrit tells him she wears all the makeup and grungey clothes to piss her dad off but he doesn't seem to notice anymore. Then, her high sort-of-boyfriend tells her the best version of rebellion is to become someone people don't even realize is rebelling.
Segue to Larissa talking about Madonna, who knows how to rebel. Interview is doing a section dedicated to Madonna's Virgin Tour. Larissa tells Carrie that virginity is so over (and HIV is still a "gay disease"), and that nobody lives in Seattle. This is perhaps a nod to the coming grunge era that Seattle boomed in, then liked so much it decided to stay a while.
The plan is for Interview to talk to all the people behind the scenes who helped make the tour. Carrie can't wait to meet Madonna at the party, which is happening, you guessed it, Friday night. Carrie muses that with Sebastian by her side at this amazing party, it will be the perfect night. Yes, Carrie, sex the first time is so perfect.
At school, Carrie misses out on an opportunity to tell Sebastian how she feels, and instead invites him to the Madonna party. She sweetens the deal by reminding him that sex is on the way, and suggesting they get a hotel room in the city for the night.
Carrie asks her father for permission to go to the party and stay at "Mouse's place" that night. Dorrit is conveniently going to a sleepover at a friend's house again. Tom acts weird and makes a bigger deal out of it than he needs to in order to go sleep with Deb that night. Dorrit walks in without the heavy makeup and dark clothes, telling Tom she doesn't need his approval. What she needs is this Miller character's approval.
Carrie goes to visit with Dorrit, who is putting on makeup in the mirror. She asks Dorrit how it's going with the boy she's been seeing and Dorrit denies everything. Carrie warns her sister that a guy should like you for who you are, not who he wants you to be. But that is in opposition to everything girls do in middle school and high school, so it will probably go unwarranted.
Mouse holds a meeting of ... random high school students? To feign a viewing of "We Are the World," but actually to get help prepping boxes of chocolate bars for a fundraiser. Donna LaDonna leads the rebellion against Mouse, and everyone follows her out the door except West, who offers to work together with Mouse.