Gypsy's. Jess, proving his smarts to us immediately, leans against a gas pump and prepares to light a cigarette. And also, why is he starting smoking now? Do we really need to watch more fake smoking? But see, Jess is in love now, so he's already decided he doesn't need cigarettes anymore, that one television cliché they won't get rid of ever. Love cures smoking. Always. A really bad song is playing in the background as Rory walks up and asks what he's going to do with that cigarette. "Depends," he says. She asks where's the part for his car. Jess pretends he can't believe Gypsy didn't leave the part for him like she said she would. More small talk. Rory asks what smoking the cigarette depends on. "What's going to happen," Jess says. "When?" Rory asks. "Now," Jess says. He pulls her in and they kiss. Rory kisses Jess much more open-mouthedly than she ever kissed CuteDean. They stop kissing and Rory says she's really glad Jess decided not to smoke the cigarette. They kiss again and Jess slowly, slowly, deliberately, carefully puts the cigarette in his pocket to smoke later. Maybe it's not love, after all. Jess says, "Well, if nothing else happens between us, at least we know that part works." He's...kind of looking at his crotch as he says that. You make the call. Rory pulls away and says she has to go. Ah, there's the Rory we know. Jess asks if he did something. Rory says this was wonderful and she looks forward to many similar occurrences in the future but she has to go right now. "Understand?" she asks. "Not at all." Rory says it's more fun this way. He kisses her goodbye and tells her to beat it. She leaves, so he can.
Rory climbs a tree and over to the window of...CuteDean. Y'all, someone needs to fire an art director. "A boy's room? I've never done a boy's room. I guess...what would teen boys like? Hmm...One dart board. Uh...one baseball flag-looking thing that they have in bars. One...picture of a guy playing football. Drew Bledsoe? I love Drew Barrymore, so this'll work. Oh, it's so boy-like and rugged! Great!" Rory knocks on Dean's gigantic, screenless window. Dean stops reading Sports Illustrated and walks over to the window hesitantly, as if at any moment Jess is going to drop down from the roof and start grabbing Rory's boobs. He opens the window. Rory says hello. He asks what she's doing. She says she climbed the tree. "Why?" he asks. Rory says she was afraid that his mom wouldn't let her in, since she probably knows about their breakup and hates Rory. CuteDean says he hasn't told his mother yet. Rory babbles that eventually his mother will know, and the thought of her eventually hating Rory really sucks, because Rory likes his mom. Dean, actually, looks upset about the breakup, because he was the only one in that relationship for a while. Rory figures that Dean will probably tell his sister, too, and that then Clara will hate her. "Well, too bad, Rory," Dean says. "Somebody doesn't like you for once." Ooh! Nice one. I love CuteDean 3.0, y'all. He asks what she wants. Rory makes a lame comment about that girl who lived in a tree for a year. CuteDean starts to shut his window, saying he's got to go. Rory: "I want to say that I'm sorry." Dean: "For what?" Rory: "For treating you the way I did. For all the things you said. I am so, so sorry. It's all my fault. I don't know what's wrong with me. You were the most amazing boyfriend in the world. You made me so happy. You made me laugh. You made my mother like you. You were nice to my friends. You protected me. You even came with me to that stupid debutante ball." CuteDean stops her, saying he doesn't need the list. Good thing, because the next would have to be, "You put up with me kissing Tristan. Then I went and kissed another boy a different time. I like kissing boys that aren't you." Rory says, "I really did love you." We all note the past tense form of the verb together. "Please believe that." CuteDean asks, "You with...him now?" Rory says she doesn't want to talk about him. "I just came to tell you that I'm truly sorry that I hurt you and that I'm going to miss you so much and I just hope that some day you won't hate me anymore." CuteDean lets out a big sigh and says, "I hope so, too." He shuts the window in Rory's face. He doesn't close the curtain, however, so she sits there watching him ignore her. Yeah. Take that, Rory. And hey, Jess? Nice that your kisses make her want to apologize to her ex-boyfriend. They remind her of shame.