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Dean Forester was Rory's first boyfriend and plays a recurring role in her life.
Dean first appeared in the Pilot where he was the new boy at Stars Hollow High School to which he had come from Chicago with his family. We discover that he had been watching Rory and was impressed by her concentration while reading. Rory even debated not going to Chilton so she could stay with Dean at Stars Hollow High. They had a quiet flirtation, and he gave 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 one was behind her back and then kissed her (Kiss and Tell). During Rory's Dance it is decided that they are officially boyfriend and girlfriend. 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. 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. 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 states that "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 behaviour and claims that she really did love him: a tearful Dean accepts her apology and closes the window on her. However, Dean soon befriends Rory again and the two seem to be all right.
It is revealed that Dean is seeing a girl named Lindsay Lister and Dean proposes to her at the end of season 3 - a few days after a fistfight with Jess who treated Rory poorly at a party. 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 as time goes by and it finally 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 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 bejewelled 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 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 both 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.