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Dean gave Rory her first kiss in the episode in Doose's Market [1] , where Dean worked for most of the series. Rory and Dean dated for most of Season 1 until Dean revealed that he is building Rory a car for their anniversary, and he tells her that he loved her. Rory reacts badly to this, stating that she needs time and this is a big step for her to take. Dean breaks up with Rory, but she doesn't tell Lorelai why. Rory drops 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 "Dean! Once Lorelai tells him that he may need to give her space in order for her to want him, he backs off. However, he later simply states to Lorelai on her porch that he can tell Rory is into Jess.

As he and Rory get closer, his marriage with Lindsay begins to fall apart.

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He tells Rory that Lindsay would like to move into a townhouse, and because of this, he needs to cut back on his time at the local college and work more hours to afford it.

Rory later rants to Lane in the market about Lindsay working Dean so hard so she can have a townhouse instead of working herself, and Lindsay overhears the conversation. Lindsay tells Dean he can't see Rory anymore, but Dean doesn't respect her wishes.

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Rory and Dean almost share a kiss when he's working at the Dragonfly Innbut they are interrupted before it happens. However, on the night of its grand opening, Dean finds Rory collecting CDs at her house, and they end up sleeping together Rory's first time. Not long afterwards, Lorelai returns home and sees the two hurriedly exit Rory's bedroom. The situation causes tension between Rory and her mother.

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Rory tries to talk about the situation with Dean the next day at Miss Patty's, but they have sex once again. Rory later goes to lunch with her mother and grandmother, and she agrees to go to Europe with Emily so she can get away from Lorelai. Before returning to the States, Rory asks her mother to deliver a letter she wrote to Dean.

Gilmore Girls - Dean Sleeps With Rory (Lorelai Fight Scene)

Her mother agrees, and hands off the letter to Dean while he's working at the market. However, Lindsay later finds the letter in Dean's jacket, and she publicly throws his belongings out their apartment window while the town watches below.

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Rory returns to Stars Hollow, and Lorelai tells her about the incident. Dean and Lindsay eventually get a divorce, and Dean and Rory get into a strained relationship. It is difficult for them to find time to see each other.

Jun 18,   Unfortunately, his personal opinion held no sway in the outcome of the series, because Sutcliffe continued, "I know they're not going to end up together, but Author: Mahita Gajanan. Nov 21,   The shocking hook-up - which occurred in the season four finale (and is shown in a little more detail in the season five premiere) when a married Dean cheats on his wife and Rory loses her.

Eventually, Rory and Dean plan to get together after Rory attends a party at her grandparents' house where Dean is supposed to pick her up at a certain time.

When Rory comes out to him late and tipsy, Dean breaks up with her because he realizes their lives are going in completely different directions.

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As Rory softly cries, Logan Huntzberger Rory's future boyfriend steps in to comfort her. In his final appearance, Dean does not see Rory, but rather Luke.

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Dean compares his faulty relationship with Rory to Luke's with Lorelai, saying that ultimately Luke would hold Lorelai back from whatever potential she may have. In the autumn, Dean randomly runs into Rory at Doose's Market.

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They've kept in touch sporadically, but haven't seen each other for a while. Dean is married with three kids and one on the way and Rory tells him about the book she's planning to write.

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Rory's bracelet is a present from Dean for her 16th birthday. It becomes a symbol of their relationship, and Dean gets very upset one day when Rory is not wearing it [26]. They'll have to write fanfic about the couple that we now know will never be.

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Do rory and doyle hook up - Join the leader in relations services and find a date today. Join and search! Is the number one destination for online dating with more relationships than any other dating or personals site. Men looking for a woman - Women looking for a woman. Dean Winchester and Jo Harvelle shared a friendship. Their relationship was damaged in "No Exit" and "Born Under a Bad Sign", although they moved on enough years later to renew their friendship when they met again in Season 5. Dean and Jo's fathers, John Winchester and Bill Harvelle respectively, were fellow hunters. John sometimes visited Harvelle's Roadhouse, where the Harvelles lived and. Apr 27,   Yeah, they had an ongoing affair. Rory lost her virginity with him at the end of season 4, and they continued hooking up in season 5. After Lindsey found out about the affair, she divorced Dean. Then Dean and Rory became a couple again, so the sex obviously continued.

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