Lorelai Being Creepy, Line-Crossing, And Or Hypocritical About, With, And To Dean-A Comprehensive Guide- Season 1
1x7, Kiss and Tell: Lorelai to Rory while talking about Rory kissing Dean: "Dean kind of looks like Christopher.â Dean talks back to Lorelai on his and Rory's chaperoned date with Lorelai and Lorelai doesn't hold a grudge for years over this. 1x9, Rory's Dance: âItâll be all sparkly and exciting, youâll be standing on the dance floor while some great looking guy stares at you so hard that you wonât even realize that Paris and Tristan have just been eaten by bears.â Dean is a "Good kid" (same episode he publicly threatens to kill Tristan)
1x10, Forgiveness and Stuff: To Luke: "He is not trouble! He's 6'2! He's beautiful! He's in love with my daughter!" The first of many instances spanning over 5 years where Luke tries to impart to Lorelai that Dean is a piece of shit and she's too blinded by lust. Lorelai finds Dean peeping in her window late at night and calmly opens the window to flirt with him, later referring to it as "The ol tapping on the window bit!" Lorelai advises Rory to "go call Dean" and "Go, talk mushy to each other, then spend an hour arguing over whoâs going to hang up first.â
1x11, Paris is Burning: Lorelai: "How many times did dean call tonight?" Rory: "Not manyâŠ3âŠ5.â "Not an all time high, but very respectable."
1x14, That Damn Donna Reed: Dean talks back to Lorelai again ("I'm not an idiot"), Lorelai is unphased. Lorelai finds out Dean and Rory were unsupervised at Babette's house, is barely phased and not panicking that they're going to fuck in the driveway. Quote: "Youâre 16 and you have the whole house to yourself for the evening, I expect youâre going to have your boyfriend over.â 1x17, The breakup Part II: Lorelai teasingly refers to Dean as "Stalker material!" after stating that he's called the house 25 times and doodled Rory's name all over his notebooks. Even though Rory asks Lorelai to get rid of a box of Dean's worthless crap she's been saving, Lorelai lies to Rory and agrees to do it but just hides the box instead. Lorelai runs to Max's house late at night to cry that Dean and Rory broke up (then Lorelai and Max have sex).
1x20, Ps I Love You: Max and Rory are alone in a classroom, a foot apart, where heâs telling her that heâs concerned about her after her breakup with Dean, which Lorelai told him about without Roryâs knowledge. Later, Lorelai tells Rory that she talked to Dean behind her back without her knowledge. Lorelai confronts Dean at work and pretends to be mad that he dumped Rory, but her loins are quivering. Dean talks back to Lorelai. Lorelai is unphased. Dean describes their breakup to Lorelai thusly "I said I love you to Rory and all she did was sit there and I donât understand why that makes me a jerk." Lorelai's first concern when cornering Rory about the breakup is how Dean is taking it. "He said I Love you and you didnât say it back? That must have been rough on him." then Lorelai imparts some confusing wisdom on Rory that glosses over the fact that Dean shouldnât be pressuring Rory to do or say anything she doesnât want to and instead is more focused on Rory living life without regrets or some shit like that. Rory looks defeated. 1x21: Love, Daisies, and Troubadours: Rory finds the box of Dean Shit Lorelai said she'd throw out. Lorelai kept it because "you're gonna want some of that stuff one day, when youâre old and married, and you can look back and say "I certainly had an interesting life!â Whatever you say Lorelai. Iâm sensing a theme here, which is that Deanâs lot in life is to make Roryâs life more interesting for her mother. "You can pull out all of your old boyfriend boxes!" We never see a Jess Box :(
Stay tuned for Part 2!














