The Most Interesting Storyline In Gilmore Girls: Rory And Dean’s Affair

rory and dean affair

This article was written by The Zillennial Zine’s spring editorial intern Fainite Auguste. Find her on Instagram at @ceilingdancing. If you would like to share an article with The Zillennial, send us an email at thezillennialzine@gmail.com.

Every year as the air gets colder and the leaves start to fall, people brew a cup of coffee, sit on the couch, and turn on Gilmore Girls. By now, most of us are nearing the end of the show. You either skipped the affair storyline or watched it through your fingers.

What is Gilmore Girls?

For those unfamiliar, Gilmore Girls is a beloved TV show that aired from 2000 to 2007. The show is set in the small town charming town of “Stars Hollow,” Connecticut. The town celebrates niche holidays, puts on events, and is full of eccentric characters like Luke, Patty, Kirk, and Lane. 

Our protagonists are the charming mother-daughter duo Lorelai and Rory. The two are only 16 years apart which makes them feel more like “sisters” than parent and child. Lorelai constantly reminds Rory that she is, perfect, the best, and the smartest. Richard and Emily also share this sentiment. There is little room for Rory to make a mistake and learn from it. For the entirety of the show, the Gilmore family constantly remind Rory that she can not get pregnant like Lorelai did. This dynamic will be the downfall of Rory as a person.

Perfect First Loves

The story begins with Rory’s acceptance into Chilton, a prestigious private school, forcing Lorelai to reconnect with her wealthy, estranged parents for financial assistance. Richard and Emily agree, but with the condition that they will be active participants in Rory and Lorelai’s life. 

In the first episode, we are shown Rory’s impulsive characteristics. She meets Dean in the halls of Stars Hollow High while packing up her things. Her teenage brain is immediately fixated on Dean. She tells her mother she no longer is interested in going to Chilton. Lorelai immediately puts two and two together and realizes it’s because of a guy, but eventually is able to convince Rory to attend Chilton.

Throughout season one, Rory and Dean find their footing in their relationship. They are the perfect small-town couple; Dean is protective of Rory but ultimately is kind to her. The couple’s first hiccup occurs when the two leave a dance early and fall asleep at Miss Patty’s dance studio and are found in the morning. Emily assumes the worst while Lorelai defends Rory.

How It all Went Wrong

In season 2 Luke’s nephew, Jess, moves to town. He’s a the classic troubled bad boy type, a foil to Dean who Lorelai loves. The season consists of a love triangle between the three teens; and eventually Rory initiates a kiss with Jess at Sookie and Jackson’s wedding and runs off. She confesses this to Lorelai, who tells her not to mention the kiss. The way this situation was handled affected Rory’s thinking about cheating; there were no consequences then. Why would she think there would be consequences later on?

@gg_and_gg_edit

ℝ𝕠𝕣𝕪 𝕒𝕟𝕕 𝕁𝕖𝕤𝕤 𝕗𝕚𝕣𝕤𝕥 𝕜𝕚𝕤𝕤 💋 #gilmoregirls #roryandjess #roryandjesskiss #gilmoregirlsedits

♬ dźwięk oryginalny – GG&GG

The Affair Timeline

Season 4, Episode 4: “Chicken Or Beef?” Dean without warning, invites Rory to his wedding. The night before his wedding Dean and some friends drunkenly stumble into Luke’s Diner. He calls out for his ex-girlfriend, Rory. Luke swoops in and moves Dean to his apartment to sleep the alcohol off. The following morning Dean and Luke skirt around the events from the night before. Luke doesn’t give him any words of wisdom, instead vaguely urges Rory not to go to the wedding.

Season 4, Episode 17: “Girls in Bikinis, Boys Doin’ the Twist” Rory, Paris, and friends go on a spring break trip. While drunk Rory and Her friends call Dean. This reignites their “friendship.”

Season 4, Episode 18: “Tick, Tick, Tick, Boom!” Rory talks badly about Dean’s new wife, Lindsay at the grocery store and she hears. What strikes me the most from Rory’s rant is the fact that she asks “what does she do all day?” Dean made it clear in season 1 that he wanted a stay at home wife.

Season 4, Episode 22 “Raincoats and Recipes”: Rory sleeps with Dean, despite him still being married. The camera follows Lorelai and pans to Rory’s bed; the pink sheets are disheveled. Lorelai knows, “What did he borrow?” The thing she’s been terrified of since Rory was fifteen finally happened.

The Breakdown

Season 5, Episode 1 “Say Goodbye to Daisy Miller” Rory tries to find support from Lane about her affair with Dean. Like any other teenager Lane sees this more as gossip and something cool that Rory did.

Season 5, Episode 2 “A Messenger, Nothing More” Rory writes her feelings for Dean out in a letter and Lindsay finds it. The pair of mothers and daughters run into each other in town. Lindsay’s mother  famous 

Season 5, Episode 4 “Tippecanoe and Taylor, Too” Dean and Lindsey divorce, Dean and Rory get back together again

Season 5, Episode 5 “We Got Us A Pippi Virgin” Lorelai tries to mend fences by inviting Dean to movie night with Luke and Rory.

Season 5, Episode 8 “The Party’s Over” Rory’s grandparents don’t like the idea of her dating Dean and try to introduce her to better suitors. Dean breaks up with Rory for the last time at her grandparents house.

What are your thoughts on Rory and Dean’s Relationship? Do you think Jess or Logan were better choices? Let us know!

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