- ‶A college degree doesn't guarantee a job, it's not like it was with our parents″
- —Dean arguing with Rory[src]
Dean is the new kid in town at first, having recently moved to Stars Hollow from Chicago in autumn 2000. He quickly notices Rory and the two embark on a long romance, which culminates in Dean cheating on his wife with Rory in 2004. Initially, Dean is a cute, smart, witty guy, who seems kind and down to earth. He doesn't come across as talkative, but a solemn type who gets on well with Rory. Dean plays softball, hockey and hangs out with guy friends, but no one he's specifically close to. He does, however, have a close relationship with his little sister, Clara.
Dean first meets Rory at Stars Hollow High School, where he was the new guy, having recently moved from Chicago with his family. He's noticed Rory and is impressed by her concentration while reading, finding 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 her 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. 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.
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 cellphone. 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 shows up to work on the Stars Hollow History Museum. He's actively dismissive of Luke and when Luke tries to talk to Dean, 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. Dean states this based on he and Luke being 'townies', although Dean is from Chicago and only moved to Stars Hollow 4 years earlier.
Dean lives in Scranton with his wife, Jenny, and their three sons and Jenny is expecting a girl. Rory bumps into him at Doose's market. He tells her he is visiting his parents and gives her news of his family. Rory then tells him she is writing a book about her mother and herself and tells him she would like to write about their relationship, her regrets and all the good he gave her, to which he agrees.
Dean and his sister are very close for the entire series, Dean often bringing Clara to town events such as the Winter Carnival and the impromptu Bracebridge Dinner town feast at the Independence Inn. Clara appears as a general kid, very enthusiastic, at times talking a mile a minute and asking all sorts of questions. As Clara grows older, she and Dean still seem to have a good relationship, although Clara is now a teen and appears to have her own life.
He and Lorelai share a friendly relationship and Lorelai has on many occasions called him "the perfect first boyfriend." She makes use of Dean's hight to do physical chores around her house (i.e. mowing, changing the water jug, and the front porch light). She considers him a pal, and has shown clear preference of him over Rory's other boyfriends. This is clearly demonstrated by her telling her after his second breakup with Rory that they - meaning Lorelai and Dean - aren't broken up, so they can remain friends.
Beth is Dean's girlfriend before his family moves to Stars Hollow. They date for about a year, but split amicably and Beth starts dating Dean's cousin. According to Lane's info, Dean doesn't feel too weird about that as he doesn't think he and Beth were really in love.
Lindsay and Dean presumably know each other from around school at Stars Hollow High, which they both attend and start dating a few months following Rory and Dean's break-up. They seem to be having a good time, enjoying a fairly regular teen relationship, until Dean impetuously asks Lindsay to marry him, which she accepts. Their marriage is foiled by Dean's obvious love for Rory as well as he and Lindsay probably not being capable of having a serious relationship, let alone a marriage, as opposed to a relaxed teen romance. They get divorced after she discovers that Dean cheated on her with Rory after reading her letter to him.
- Main article: Rory and Dean
Dean is Rory's first boyfriend, and she later loses her virginity to him despite him being married at the time. Despite not being an avid reader, Dean reads the books Rory recommends to him, and he is patient when it comes to her book-shopping. Dean tells Rory he'll attend a four-year college, Southern Connecticut State, per her influence on him. He later cuts back on school when he's married because Lindsay wants a townhouse and they need more money, so he gets a job. He then eventually drops out of school altogether. Whether or not he picks it back up is not mentioned. Rory references Dean during a therapy session after returning to Yale. She is in therapy after taking time off from school; she states "I never stole a boat with Dean!.... My married ex-boyfriend who I lost my virginity to!"
- 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 or he was just lying to appease Lorelai
- 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, and she is with him 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.
- Before Padalecki was cast, two pilots were shot with other actors portraying Dean, the second of which was Nathan Wetherington
- Jared Padalecki left Gilmore Girls after landing a lead role on Supernatural
- In Defense of Dean Forester: Why 'Supernatural's Jared Padalecki Was the Ultimate 'Gilmore Girls' Guy (BUSTLE • MARCH 2014)