Dean Forester was Rory's first boyfriend, and played a recurring role in her life.
Dean first appeared in the Pilot episode where he was the new boy at Stars Hollow High School, having recently moved from Chicago with his family. We discover that he had been watching Rory and was impressed by her concentration while reading. Before Rory goes to Chilton, she and Dean meet and experience shy love. Rory even debates not attending Chilton so that she could stay with Dean at Stars Hollow High School. They have a quiet flirtation and he gives Rory a bracelet for her birthday (which he made out of a coin).
Rory and Dean shared their first kiss at Doose's Market where Dean worked. Dean initiated this kiss by offering Rory free "pop" where he made her guess which was behind his back and then kissed her. After that, Rory ran away with cornstarch and kept it on her desk to remind her of the kiss. During Rory's Dance it is decided that they are officially boyfriend and girlfriend. In the same episode, Dean and Rory's (in her opinion) rude and annoying classmate, Tristan Dugray, who "has a thing" for Rory. Despite this, they continue to date happily until the episode Star-Crossed Lovers and Other Strangers when 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. She also thinks this because of her mother getting pregnant so early. In the following episode 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, in the final episode Rory drops significant hints (like at the town meeting) that she misses Dean and really does love him, resulting 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 more and more attractive. They both share the same interests in both literature and music. Rory feels confused about him at first since she knew he was trouble, but she still ends up being good friends with him. This causes Dean to become very possessive of Rory, until Lorelai tells him to back off and calm down; he does so but in the 18th episode 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 town dance after her insistent attention to Jess over him and he calls out on Rory how he knows how she feels and claims he's "out".
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. A tearful Dean accepts her apology and closes the window on her. Dean soon befriends her again, however, and the two seem to be all right.
It is revealed that Dean is seeing a girl named Lindsay Lister. Dean proposes to her at the end of season 3 — Rory first reacts badly to the news, but later accepts it. Dean marries Lindsay in Season 4 and, while their marriage is a happy one at first, cracks begin to show and Rory and Dean seem to grow closer. Lindsay tries hard to be a good wife to Dean and is hurt when he brushes her aside. Tensions increase when he yells at her for answering his cellphone. She overhears Rory criticizing her, saying that she doesn't know what's good for Dean, and she tells him to stay away from Rory. The situation culminates in Dean cheating on Lindsay with Rory; Dean claims he's leaving her, but while Rory is in Europe he stays with his wife until she finds a letter written to him by Rory. She promptly throws his stuff out of their apartment and they file for divorce.
Dean and Rory begin dating but the tension and time apart has clearly taken its toll and the couple find themselves unable to go on dates as Dean works three jobs and Rory has school. They find the time however on the same evening Rory's grandparents throw her a party, but as a slightly tipsy and bejeweled Rory arrives late for her pickup, Dean simply states that he doesn't belong here anymore, having realized that their lives are too different and heading in different directions, and Rory only answers with a sympathetic "Dean...": this breakup is the final one the couple have.
His final appearance is in To Live and Let Diorama where he relates his faulty relationship with Rory to Luke's with Lorelai, saying that ultimately, Luke would hold Lorelai back from whatever potential she may have. With this statement, Dean is never heard from again.
For more detail, see: Rory's relationship with Dean
- He and Lorelai share a friendly relationship and Lorelai has on many occasions called him "the perfect first boyfriend" and considers him a pal, and has shown clear preference of him over Rory's other boyfriends.
- He is frequently referred to as "gorgeous" by the women who encounter him.
- Jared Padalecki's height is a recurring theme to the character, as Lorelai, Miss Patty, Louise and others comment on it and make jokes about it.
- In 1.15, he mentions having a Suzuki motorcycle. In the same episode he and Luke played softball.
- His father sells stereo systems, and his mother transcribes medical documents 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 was a hockey player on his high school team. His hockey jersey spelled his last name "Forrester" with two R's instead of one.
- Before Rory, he had a serious girlfriend named Beth. They parted on amicable terms when he moved to Stars Hollow.
- He went to Southern Connecticut State before dropping out.
- His mother's name is Barbara.