The foreshadowing in Gilmore Girls surprisingly deep to rewatch.

The series excels at subtly planting seeds of doubt and longing, using Rory's reactions and Dean's quiet desperation to foreshadow the explosive collision of their unresolved feelings. The storyline was even doubled down on in Rory’s "worst" Gilmore Girls moment.

Rory's Negative Reaction To Learning Dean Is Getting Married

Rory Can’t Hide Her Surprise And Concern

In season 3, episode 20, “Say Goodnight Gracie”, Dean pulls Rory aside after Fran’s funeral. He seems anxious and excited when he announces he is engaged to Gilmore Girls’ Lindsay. Rory’s initial response is almost nonverbal, clearly taken aback by the news, and Dean presses her for a response, saying, “So, what do you think?” and Rory’s first instinct is to ask, “Why now?”, followed by a series of logistical questions about their age and his ambitions to go to college. Rory does not criticize Lindsay personally, but his decision to marry young to someone he hasn’t known for long.

Dean does not take Rory’s reaction to his news well. The only thing he seems to want from Rory is congratulations, and he expresses his disappointment in her reaction. He then lashes out at Rory, suggesting she is only not happy for him because Jess treats her poorly. However, it seems unfair that Dean expects a perfect reaction from Rory - springing the news on her at a funeral is not the ideal setting, although he arguably wants Rory to hear it from him rather than through town gossip. Rory tries to argue that she is only taken by surprise.

Dean Mumbles Rory's Name On His Bachelor Party

Dean Remains Heartbroken That Rory Didn’t Want Him

In season 4, episode 4, “Chicken or Beef?”, Dean has a bachelor party and winds up at Luke’s with his friends. Luke initially offers them all pancakes, but after Dean starts mumbling Rory’s name at the counter, he dismisses his friends and puts him up to bed. Dean carries on with his drunken rambling about Rory, talking about her intelligence and “pretty hair”. Once he is about to drift off to sleep, he says plainly, “I miss her” and “Why didn’t she love me?”

Their situations are comparable, with Luke having just married Nicole...

Despite Dean liking the idea of marriage and wanting to move on, this scene shows that he has not really moved on from Rory. Significantly, Luke is there to Dean in this scene, and he does not seem to have anything to say. This could be because he does not think it is his place, but their situations are also comparable, with Luke having just married Nicole. This scene shows how doomed Dean’s relationship with Lindsay is, and the inevitability of the unresolved feelings between Dean and Rory coming to the surface.

Rory Calls Dean On Spring Break

Rory Leaves A Voicemail For Dean While Drunk

In season 4, episode 17, “Girls in Bikinis, Boys Doin’ the Twist”, Rory spends Spring Break with Paris and other friends. Over drinks, the topic of relationships comes up, and Rory breaks the news to her friends that Dean is married. Madeleine and Louise echo Rory’s previous incredulous reaction and the question, “Why?”, reinforcing that it is arguably a natural initial reaction regarding someone in their age group. Louise goes on to give a future prediction that Dean and Lindsay’s marriage will not work because he is still in love with Rory.

This alone shows that the writing on the wall about Rory and Dean is obvious to everybody around them. After this, Madeleine dials Dean’s number and es Rory’s phone back to her to leave Dean a voicemail. Rather than simply hanging up the phone, Rory leaves a drunken voicemail, saying she is on Spring Break and that Madeleine is “evil” for drunk dialling his number. Although they are still friends, Rory begins to toe the line with their boundaries. Rory also talks about how his new wife is pretty, tall, blonde, and leggy, letting her jealousy show.

Rory Complains About Dean Quitting School

Rory Is Upset That Dean Is Dropping Out

In season 4, episode 18, aptly titled “Tick, Tick, Tick, Boom”, the ticking clock of Dean and Lindsay’s marriage intensifies. Dean seems to be giving in to the pressure of other people’s expectations and losing touch with what he truly wants out of life. Initially, in this episode, Rory only contributes to the pressure surrounding Dean, who is one of Gilmore Girls’ best love interests. Her way of approaching the conversation makes it easy to understand why Dean is defensive about it.

When he tells Rory he is going to be dropping out of school to earn enough money to buy a town house for him and Lindsay, Rory gives him her honest opinion, telling him that a lot of people drop out, saying it will be temporary, but then they could lose their momentum for study. Dean fires back, saying, “Have a little faith”, and Rory has clearly struck a nerve. Rory’s concern about Dean’s future is being a friend from her point of view, but the extent to which it bothers her is telling.

Rory's Rant About Lindsay In Doose's Market

Rory Calls Lindsay “Selfish” And She Overhears

Later in “Tick, Tick, Tick, Boom”, Rory complains about Dean’s work situation in Doose’s Market with Lane. She says that, if anything, she is angrier with Lindsay because she is being “selfish” by pushing Dean to work rather than be in school. Lindsay overhears, and later in the episode, viewers learn that Dean had not informed Lindsay that he and Rory were still talking. That Lindsay does not seem to know Rory is involved with his life in any way sets the tone for secrecy and crossed boundaries, arguably adding sympathy to Lindsay’s plight in Gilmore Girls.

Lindsay tells Dean not to talk to Rory anymore, but it only seems to bring them closer together - Dean says that ceasing with Rory is “not going to happen”, the secrecy setting the stage for the cheating storyline. That Lindsay is not comfortable with him speaking to someone who cares about his college ambitions and is trying to be a positive influence further worsens his sense of isolation and unhappiness. Although it does not excuse their actions, it provides the context for the inevitable event. Rory said their sleeping together “just happened”, but there is a clear buildup.

Dean Tells Rory She's The Only One Who Cares About His Future

Dean Feels Pressure From All Sides, While Rory Is ive

In the same episode, Dean and Rory have both reflected on their argument regarding his schooling by later in the episode. Showing their mutual care for each other, they both apologize - Dean, for lashing out defensively, and Rory, who concedes that he should make his own decisions about his life. She goes on to tell him she only wants the best for him, in line with her expressed reservations about his engagement to Lindsay. Dean agrees and goes on to tell Rory that she is seemingly the only one who wants the best for him.

This further fuels the setup for Rory and Dean’s cheating storyline - Dean seems to have pressure from all sides at this pivotal time in his life. He seems to enjoy his work in construction and feels good about earning money, which he is correct in pointing out Rory has an “elitist” judgment about. However, Rory also has a point in telling Lane how smart Dean is and that he is limiting his options at his wife’s behest. However, Rory’s assertion that he should make his own decisions makes Rory seem like the only one who prioritizes Dean’s happiness.

Dean Picks Rory Up From The Bar After Her Bad Date

Dean & Rory Have A Dinner Date Of Their Own At The Bar

The Rory and Dean scenes come thick and fast in season 4, with another major moment in episode 21, “Last Week’s Fights, This Week’s Tights”. In the episode, Rory is on a bad date and realizes she does not have any cash - a member of staff advises her that there is an ATM a few blocks down, but it is “dicey” at night. Rory then asks Dean to pick her up from the bar, claiming, “I didn’t know who else to call.” When he arrives, they have dinner together, and Dean takes her back to campus.

This episode further sets up the cheating storyline, with Dean saying, “It’s good to get out, it’s good to laugh,” implying he feels cooped up and miserable in his marriage. Rory also asks him how it is possible he can be out with her following Lindsay’s forbidding him to speak to Rory, and Dean is evasive. Rory probes him for more information about his situation, but their conversation is cut short, building the suspense for the seemingly inevitable cheating storyline.

Dean & Rory Almost Kiss At The Dragonfly Inn

Dean’s Protectiveness Is Called Into Question

Dean and Rory’s almost-kiss occurs in the same episode they sleep together - season 4, episode 22, “Raincoats and Recipes”, right after this buildup of small moments between them that set the scene. Dean and Rory had steadily moved closer together over the previous few episodes. While Dean is helping Lorelai with some manual labor at the Dragonfly Inn, Rory and Dean have a tense conversation about Jess turning up at the end of the previous episode.

Rory tells Dean Jess didn’t stay, and Dean gives terse responses, giving away his disapproval of their relationship. Rory then pushes harder for clarity from Dean than she did in the previous episode. She presses him to explain why her relationship with Jess means so much to him, and why he feels so protective of her. As the conversation continues and Dean confirms he is her friend, he leans in for a kiss, which is cut short by a ing colleague interrupting.

Rory its She Messed Up With Dean

Rory Compares Dean With Jess

In the same episode, “Raincoats and Recipes”, Rory reflects on her past behaviors in a conversation with Lane. She refers to her relationship timeline with Dean in Gilmore Girls when she chats with Lane over Pringles. She tells her how “awful” it was when Jess had shown up out of nowhere the night before and asked her to go away with him to start a new life in New York. Lane points out that part of Jess’ appeal is his unpredictability.

In comparison, Dean was Rory’s “safe” boyfriend who got away. She its to Lane, “I think I really blew it there, you know? I didn’t appreciate it” when she is reminiscing about Dean, who made her feel that “I always knew that no matter what happened, he would be there”. By lamenting that she sabotaged her safe and loving relationship in favor of one she finds unreliable, she shows that she still has strong feelings for Dean.

Rory Was Reckless About Dean As Early As The Pilot

Lorelai Confronts Rory About Dean In The First Episode

The pilot episode of Gilmore Girls is probably one of the best in television in the way it sets up the key relationships in the show. The characters do grow and evolve beyond how they present initially, but Amy Sherman-Palladino does an excellent job with how she sets up Lorelai and Rory as mirroring each other. Ultimately, she honors this repetition of history in A Year in the Life. The events of the pilot episode set up Rory’s essential flaws throughout Gilmore Girls beneath her image as the “special” and “smart” girl with a bright future.

Rory even makes a prophetic joke when she first meets Dean and he talks about her unbelievable reading concentration - “Maybe I just didn’t look up because I’m unbelievably self-centered”, a key trait that makes a lot of viewers dislike Rory and which ultimately informs her imperfect decision-making. More significantly, though, right after meeting this romantic interest, Rory expresses her reservations about going to Chilton.

Logistics thinly veil her true motivation - the new boy in town...

Just like she does about Dean’s decisions in seasons 3 and 4, Rory backs this up with logistical details, like the journey time and that Lorelai’s money should be going toward buying an inn with Sookie. However, logistics thinly veil her true motivation - the new boy in town - which is uncovered later. This culminates in an intervention by Lorelai. Lorelai points out, “You’ve always been the sensible one in this house,” which foreshadows another key time Lorelai points out Rory’s usual rational thinking when Rory sleeps with Dean in Gilmore Girls season 4. She also plays the “mom card” in both scenes.