On the walk home, Lorelai wonders what kind of a world is it where no one has rented Willy Wonka. She tells Rory that she has good news and that CuteDean is coming to watch the movie, too. Rory does not find this to be good news at all. She starts whining that she didn't want her first date with CuteDean to be with her mother. She says that this isn't Amish country and that boys and girls aren't supposed to have dates with their mother hanging around. Lorelai says she wasn't thinking of this as a date but more like a "hanging out session." Rory wonders in what universe would Lorelai think that Rory would want to first hang out with CuteDean with her mother. Lorelai asks Rory to stop saying the word "mother" like that -- "like there's supposed to be another word after it." Rory says she feels humiliated. Lorelai assures her that she's just overreacting. Rory can't believe that this boy she likes is now forced to come over and "eat crap and watch a movie." Lorelai continues to whine that she was just trying to do a nice thing, but the more she whines, the more she looks like my last boss who used to wiggle and moan outside my office door, begging me to go get drunk with her after work. Rory says that this is like Lorelai's mother inviting a boy Lorelai liked over for dinner. Lorelai is crushed at the notion of comparing her to her mother and says she'll tell CuteDean that the movie night is cancelled. Rory says she can't cancel or it'll look like she wigged out. Lorelai says she'll just stay hidden in the other room and leave them alone. Rory says that'll look like her mother arranged a date for her. "What'll we do?" Lorelai asks. "He has to come," Rory says, with this incredible pout that shows the fear and nausea of having to have the boy you like hang out at your house and meet your family before you're even sure if he likes you. Because you want the boy to really, really like you before he enters the house. When he enters the house, he gets an idea of What You'll Become. You want him secure in his likehood before he gets a chance to back out at the vision of you washing dishes and dancing to A-Ha. Rory and Lorelai both put on fake smiles and try and pretend it'll be fine.
Lorelai finds Rory in her bedroom with all of her clothes on her bed. She's just staring at all of the sweaters and tops as they sit in a pile. Lorelai offers to help her get ready for CuteDean. Rory says that she's "supposed to look pretty and girlie, which is completely impossible because [she's] gross and [she has] nothing to wear." Lorelai picks up a purple sweater and roots around until she finds a top that says "hip" and "cute" but also "relaxed." Rory marvels at how her mother can turn a top into an outfit. Lorelai says she has years of experience in the "fashion brain-freeze." Rory asks how her mother is so good with men. She says that Lorelai's always funny and makes them laugh and then does this hair-flip thing (Lorelai corrects her and shows that it's actually a twirl) and completely amazes the guy. Rory says she'll never be able to do that: "Trig, I can do. But boys? And dating? I'm a total spaz." Lorelai sits down next to Rory and says, "Listen. The talking part? You just get used to. The hair twirl I can teach you. The leaving him amazed part? With your brain and killer eyes, I'm not worried." She tells Rory just to give it time and she'll get better at these things. She tells Rory to hustle and get ready. "We've got a man coming over."