Countdown to Gilmore Girls: A Year in the Life – 24 Days Left

Written by M.

24 DAYS LEFT!! We are officially in the month of November, the month that will bring us Gilmore Girls: A Year in the Life!


Crash Course lesson # 10.

Who is Dean Forester?

Dean is Rory’s first boyfriend, and has a recurring role in her life. He was termed as the “perfect first boyfriend” by Rory and she had a relationship with him three different times. Dean worked at Doose’s Market during high school, where he and Rory had their first kiss. He departed the series in Season 5.


Dean first meets Rory at Stars Hollow High School, where he was the new guy, having recently moved from Chicago with his family. He noticed Rory, is impressed by her concentration while reading and finds her interesting. Before Rory heads to Chilton, she and Dean experience shy love and Rory even debates not attending Chilton so that she could stay with Dean at Stars Hollow High. They have a quiet flirtation and Dean gives Rory a bracelet for her birthday (which he made). Rory initially keeps the budding romance a secret from her mother, Lorelai. Rory and Dean share their first kiss at Doose’s Market where Dean works. Dean initiates the kiss by offering Rory free “pop”, making her guess which was behind his back and then kissed her.


After that, Rory runs away, unintentionally shoplifting cornstarch, which she kept on her desk as a memento of the kiss. Rory hesitantly asks Dean to attend a Chilton dance with her and Dean agrees, after some persuasion. When they arrive, they agree to keep the evening spent at the dance brief as it’s neither of their type of event. When Louise tries to flirt with Dean, he turns Louise’s compliment about his height to Rory who responds that she doesn’t mind so much in heels.

Before Dean and Rory are about to leave the dance, Rory’s (in her opinion) bothersome and troubled classmate, Tristan Dugray (who has “a thing” for Rory), gets into a public confrontation with Dean where Dean defends himself successfully, and Tristan is left embarrassed and surprised. Despite this, Dean and Rory continue the evening in Stars Hollow. As they are walking through town, Rory tentatively asks Dean if he’s her boyfriend to which he asks her if she wants him to be. This prompts them to declare each other boyfriend and girlfriend. They continue to date happily until Dean reveals that he is building Rory a car for their six month anniversary and tells her that he loves her. Rory reacts badly to this, stating that she needs time, and this is a big step to take, Dean is really hurt and breaks up with her. The night after that, Rory and Lane go to the birthday party of Madeline, where she ends up kissing Tristan. After the break-up, Rory reveals that Dean broke up with her because she didn’t respond with “I love you too.” This break, however, doesn’t last long. After months, Rory starts to drop significant hints (like at the town meeting) that she misses Dean and really does love him, resulting in him turning up at Chilton where Rory tells him that she loves him, and they get back together.

When the new school year starts, it’s time to reenact Shakespeare and Rory is teamed up with Paris, Madeline, Louise, Brad and Tristan. And Rory and Tristan are chosen to play Romeo and Juliet at the death scene. This makes Dean jealous and worried, since he hates Tristan. Tristan however gets into trouble and is pulled out of school before the reenactment and he says his goodbye to Rory with a very jealous Dean watching close by.


Their relationship goes well until the arrival of Luke’s nephew, Jess Mariano, whom Rory finds herself drawn to. They both share the same interests in literature and music. Rory feels confused about him at first since she suspected he was trouble and her mother didn’t trust him, but she still ends up being good friends with him. Dean notices Rory growing distant with him as she grows closer to Jess. This causes insecure feelings about his relationship with Rory to manifest, and he begins clinging to her to the point where it becomes frustrating for Rory. Lorelai tells him that sometimes the best thing someone can do to help a stressful situation is to give the other person a little space. Dean sees her point and realizes he’s been crowding Rory, and he pulls back. In the 18th episode, however, Lorelai finds him on their porch where he simply says, “She likes Jess, doesn’t she?”

In Season 3, Dean breaks up with Rory at a 24-hour dance marathon the town is hosting. Rory is partnered with her mother for the dance, and as the event unfolds, Dean finally cracks at the obvious sight of jealously Rory is demonstrating over Jess. He publicly calls the two out on their feelings for each other, tells Rory he’s “not her boyfriend anymore,” and walks out which prompts Rory and Jess to begin their relationship.

Rory later climbs a tree to knock on Dean’s window, attempting to apologize for her behavior and claiming that she really did love him. Dean is still distraught over the conclusion of their relationship and closes the window on her, showing that he does not accept her apology. As time passes, however, Dean approaches Rory where he expresses that he wishes for them to be friends. She readily accepts.

During a hockey game, it is revealed that Dean is dating a girl named Lindsay Lister. Rory is confused as to how she feels about Dean moving on, and she admits that she wished he would pine for her a little to Lane. It is later shown that Lindsay does not trust Rory’s friendship with Dean when she seemingly glares at her during a town meeting (which she is attending with Dean next to her). A local boy, Kyle, throws a party at his house while his parents are away; Dean goes to the party with Lindsay. The couple have a brief conversation with Rory. Later in the evening, Dean is on the staircase with his girlfriend when Rory comes downstairs crying. When Jess follows her, Dean puts two and two together and realizes that Jess made her cry, and he punches Jess for whatever he did to upset Rory. The two continue their fight throughout the house and eventually onto the front lawn. The fight ends when they are pulled apart, and the cops quickly appear on the scene.One would think the fight would prompt insecurities about Dean’s feelings for Lindsay, but it is then discovered Dean proposed to her. Rory first reacts badly to the news, but later accepts it. She tells Dean to order whatever he and Lindsay wishes in a home catalog so she can gift it to him as their wedding present. Dean invites Rory and her mother to his wedding, but after some intervention from Luke (who heard Dean confess his remaining feelings for Rory the night before whilst he was drunk), the two decide to not attend.


Dean marries Lindsay in Season 4. While their marriage is a happy one at first, cracks begin to show, and Rory and Dean seem to grow closer. Lindsay tries to be a good wife to Dean, but she is hurt when he begins brushing her aside. Tensions increase when he yells at her for answering his cell phone. She overhears Rory criticizing her in the market, saying that she doesn’t know what’s good for Dean, and Lindsay tells him to no longer be friends with Rory. The old attraction and romance between Dean and Rory slowly builds again, and it eventually reaches its peak when the two have sex in Rory’s bedroom at her mother’s house. Lorelai unexpectedly comes home not long after, and she discovers them both hurriedly walking out of the bedroom. Dean promptly excuses himself, but overhears Lorelai and Rory fighting (as it didn’t take Lorelai long to figure out the situation). Rory tries to defend the situation when she says Dean said he was leaving Lindsay because the marriage was over. Rory initially tries to fix the situation when she asks Dean to meet her at Miss Patty’s so they can talk. However, they only accomplish having sex once again. She later leaves for Europe with her grandmother to get away from her mother, and while she is gone, Dean remains with his wife. Rory writes a letter to Dean while she is away, and Lorelai delivers it to him. It isn’t until Lindsay discovers the letter that she realizes Dean cheated on her, throws his belongings publicly out their apartment window, and they divorce.

Afterwards, Dean and Rory begin dating, but the affair and their time spent apart has clearly taken its toll. Lorelai is uncomfortable with the relationship because of how it began, and the couple also find themselves unable to go on dates as Dean works three jobs and Rory has school. When they do go on dates, someone is usually in the way or the time is brief because of their busy schedules. They plan for a date on an evening Rory is attending a party at her grandparents’ house. Dean had agreed to pick Rory up at a specific time, but when Rory comes out to him late and tipsy, he realizes they are no longer right for each other as their lives are headed in different directions. He leaves, and Rory softly cries as her future boyfriend, Logan, comforts her.

Dean’s final appearance is in To Live and Let Diorama where he compares his faulty relationship with Rory to Luke’s with Lorelai, saying Luke ultimately would hold Lorelai back from whatever potential she may have. With this statement, Dean concludes his five seasons worth of appearances.

Dean figured out how to keep the Gilmore Girls happy very early on and is willing to share his dating guide.


To me Dean is seriously one of the most boring characters of the series. Though most of the characters have multiple layers, Dean is an one layer character. The only thing he cares about is Rory and he broke up with her three times(!), because he felt a little insecure. The most exciting thing he has done is cheat on Lindsay, with Rory.


  • Dean’s allergic to walnuts.
  • Dean is an accomplished mechanic, able to build a car from acquired parts. His father and his paternal grandfather both worked leisurely on cars also.
  • He likes Nick Drake, Liz Phair and The Sugarplastic.
  • Dean likes Lord of the Rings, Neil Young and Battle Bots.
  • Jared Padalecki’s height (6’4″) is a recurring theme to the character as Lorelai, Miss Patty, Jess, Louise and others comment on it and make jokes about it.
  • Dean mentions having a Suzuki motorcycle (but it is never seen). This is contradicted, however, in the beginning of the series when Lorelai tells him Rory won’t be going on his motorcycle, and he states he doesn’t own one.
  • Dean and Luke used to play softball sometimes on the weekends.
  • His father sells stereo systems, and his mother transcribes medical records part time.
  • He has a younger sister named Clara who rides horses, and he has mentioned that he has an older sister as well. He is close to Clara, she is with him at the Bracebridge Dinner and when they go to the carnival with Rory and Jess.
  • He is a hockey player on his high school team. His hockey jersey spelled his last name “Forrester” with two R’s instead of one.
  • Dean states that he likes to the idea of a wife making her husband dinner because he was raised in a family where his mother did that for his father. This is especially important when he and Rory get into an argument over the Donna Reed Show.
  • Dean visits his hometown, Chicago, two summers in a row. The first is mentioned when Rory fractures her arm in a car accident, and the second is shown when his letters addressed to Rory (who is in Washington D.C.) state his return address as being Chicago, IL. He visits his grandmother while he is there.
  • Jared Padalecki’s departure from Gilmore Girls was due to his then new role on the TV series, Supernatural, for which Padalecki is best known.

Have love,

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