The episode begins with Carrie and Sebastian playing a dice game when Sebastian professes his love for her. As an answer, Carrie tells him that she wants to have sex with him. At the diner, Carrie is embarrassed about voicing her thoughts and tells Mouse that she is feeling bad about it. At home, the phone rings and Dorritt and Tom rush to pick up the call. It is Deb and Dorritt is disappointed. She leaves to go to the record store. Deb and Tom are dating and Tom tells Deb that he hasn’t told his children yet. Deb wants him to come over to her place for a “night cap” and they decide on the next Friday. Deb tells Tom to come prepared.
At Interview, Larissa tells Carrie that they are going to do a section of the magazine dedicated to the Virgin Tour. Larisa tells Carrie that Madonna is launching the tour in Seattle and the party is going to be at the Plaza. They are getting the clothes from the show and Andy wants to do a ‘Bahamas’ theme. Larissa tells Carrie that she could attend the party with Sebastian. Carrie is excited and she tells Sebastian about the party. She later adds that they could spend the night in one of the hotel room. Sebastian likes the sound of it. At home, Carrie tells Tom about the party and asks him if she could go. Tom agrees. He seems pretty happy because now he can have the night cap with Deb.
Dorritt arrives to get some breakfast and she isn’t wearing any makeup and she is looking nice. Carrie at once realizes that Dorritt is seeing a guy. She asks Dorritt about the guy in her life. Dorritt tells her about Miller, and Carrie tells her that Miller should like her for who she is and not what he wants her to be. Dorritt says that she doesn’t want to take any advice from Carrie. At school, Mouse is trying to get some extracurricular activities done and West decides to help her. Carrie and Sebastian arrive at the party and Larissa and Benet tell them that they need to go to the VIP lounge. The person at the door says that Carrie’s name is on the list, but they don’t see Sebastian’s.
At school, West is still helping Mouse and Mouse thinks that he is flirting with her so that he can mess up her grades. West tells Mouse that he likes her and will do nothing that would harm her. Mouse is unable to resist West’s charm and she ends up kissing him. At home, Tom asks Harlan for some advice. He wants to know what a woman means when she says “come prepared”. Harlan tells Tom that he needs to carry some condoms when he goes over to Deb’s. Tom is nervous, but excited.
At the party, Sebastian tells Carrie that they can have their special evening even without being VIP. Carrie doesn’t agree to that. She is determined about her special evening and so she goes into the VIP area to look for Larissa, but is unable to find her. She finds Benet and tells him about the situation. He tells her to find a guy with a “big wrist” and ask him to talk to the gatekeeper. Carrie is worried but decides to follow Benet’s advice. He walks up to a “big guy” and tells him about the situation. The guy loves “love stories” and he tells her that the first time he kissed his boyfriend was during one of Madonna’s concerts. Carrie is surprised to learn that the big guy is gay. He also tells her that his boyfriend is the one handling the entry into the VIP area and that he would talk to him.
At the diner, Donna finds Dorritt reading a book. She also notices Dorritt’s ‘no makeup’ look. She at once realizes that there is a guy in her life. Dorritt tells Donna that she would never change herself for a guy. Donna tells her that there is no harm in changing her looks for a guy she likes. Dorritt seems a little confused because that is not what Carrie told her. At the party, Carrie manages to get Sebastian into the VIP area. Tom is at Deb’s place and Deb leads Tom into her bedroom and they get at it.
Later, Tom wakes up to go to the bathroom and he runs into Deb’s son, naked. Tom is embarrassed but Don, the son, does not react much and guides him to the bathroom. Tom starts getting dressed and Deb asks what is going on. Tom is not at all happy that they had sex when her son was in the house. Deb tells him that her ex was supposed to take Don, but he cancelled. She also says that she doesn’t get to see Tom because of their busy schedules and she didn’t want to cancel the “night cap”. Tom tells her that it was wrong of her to do something like this and Deb is pissed that she is being judged. She asks him to leave. At the party, Carrie and Sebastian decide to spend some time alone.
Sebastian goes to get some drinks and Benet tells Carrie that the party is going to be over soon. He says that he hasn’t gotten a chance to talk to many people and get their quotes. He asks Carrie to help him. He wants her to talk to Billy, Madonna’s songwriter and get a quote from him. Carrie is excited and doesn’t want to lose this chance. She tells Sebastian that she has some work to do. Sebastian is fine with it. She talks to Billy and manages to get a quote from him.
The party is over and Carrie is excited that finally she will have her name in the magazine. Sebastian is pissed. He tells her that this night was supposed to be theirs and Carrie managed to make it her night. He is also pissed about the fact that when he told Carrie that he loved her, she didn’t reply. He thinks that she doesn’t love him. Carrie tells him that she was waiting for the perfect moment. Sebastian feels that she thinks too much about things. Carrie tells him that is how she is and if he cannot deal with that, they should break up. Sebastian agrees if that is what she wants.
At home, Carrie tells Mouse that she loves Sebastian. She is also upset that Sebastian did not fight for her and he let her go easily. Mouse assures her that things would get better. The next day, at the diner, Tom meets Deb. He tells her that he is sorry for being insensitive towards her situation. He feels that he shouldn’t have walked out on her and apologizes for his actions. Deb tells her that if they are dating, they are bound to have fights and it is normal. Deb promises to get a babysitter the next time they decide to have a night cap. Tom is relieved.
Next, West tells Mouse that he really likes her and that he wants to go out on a date with her. Mouse agrees. Dorritt brings Miller home and they decide to have sex. Carrie is lonely and upset and for the first time, she is unable to write down her thoughts in her diary. She goes to bed The episode ends.