Having just watched "Let the Games Begin," it's so easy to see the through-line directly from there to the end of Season 4, in a way that makes it feel almost depressingly inevitable, haha. Jess is the guy Rory wants, but doesn't want to want, and Dean is the guy who Rory doesn't want, but desperately WANTS to. Her desire for Jess, at this point, she almost seems to view as an embodiment of her chaotic impulsive streak, which definitely existed long before Jess moved to Stars Hollow, but has seemed increasingly hard for her to control. And this is something Rory really doesn't like about herself. In her mind, her desire for Jess, this overpowering, uncontrollable thing, has "made" her hurt the people she cares about. It "made" her hurt her mother (she missed her graduation), it "made" her hurt Dean (whom she HAD loved, still cares about, and believes "deserves" her love), severed her relationship with Dean's family, and will make literally everyone else in her life (except for Luke) unhappy. She has let everyone down because she couldn't control her own feelings. It's interesting that she doesn't seem to blame Jess himself for this, but she blames herself for liking him, which... If you're going into a relationship hating yourself for liking the other person, that's not really a recipe for a healthy relationship. 😭 Rory made her pro/con list at the end of the summer and concluded that Dean was the superior choice (nevermind how her own anger over seeing Jess kiss someone else might have skewed her "study"), but she couldn't seem to make herself act "rationally," and that was a Failure. So... the end of Season 4 rolls around, and Rory WANTS Dean again (just like she was supposed to, right?), and she's told Jess NO, she DIDN'T want to be with him! And probably actually meant it this time (helped along by Jess himself, poor bastard)! So that means she's finally feeling the way she should be and everything will be right again! Right?
