11) When Dean breaks up with Rory Season 3, Episode 7: “They Shoot Gilmores, Don’t They?”
Rory likes Jess and Jess likes Rory. Seems simple, but it’s not. Why? Because Rory is still with Dean and Jess is with, well, a random girl. When Dean realizes what’s up after attempting to dance for 24 hours at the Stars Hollow Dance Marathon, he breaks up with her in front of the town.
12) When Rory gets into Harvard, Princeton, and Yale Season 3, Episode 17: “A Tale of Poes and Fire”
Rory was able to use one of her favorite decision-making tools, the pros and cons list-to decide between the colleges of her dreams. Originally set on Harvard, after a few speeches from her grandfather, a proud Yale alum, Rory decides pro for Yale.
13) Rory’s Chilton Graduation Speech Season 3, Episode 22: “Those Are Strings, Pinocchio” “As she guided me through these incredible 18 years, I don’t think she realized that the person I wanted to be most of all was her.”
Rory’s valedictorian speech at her high school graduation-with a special dedication to her mother-is one of the most heartwarming moments from the series. Even Luke cried.
14) Luke and Lorelai’s first kiss Season 4, Episode 22: “Raincoats and Recipes” “Will you just stand still?”
After four loooong seasons and a few awkward first dates, Luke and Lorelai finally share their first kiss. Though it’s interrupted by a terrified, naked, sleepwalking Kirk, it’s a classic Stars Hollow first kiss.
15) When Dean and Rory have sex Season 4, Episode 22: “Raincoats and Recipes”
While Lorelai explores a new relationship with Luke, Rory explores an old one with her former high-school fling. Now married, Dean is bored of his mundane life and Rory, who feels like she’s failing at Yale, is in search of familiarity. Rory’s decision to lose her virginity to her ex is the beginning of Lorelai and Rory’s major fall out.
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