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The season picks up at the exact point the previous season ended, with Lorelai embarking on a relationship with Luke and Rory beginning an affair with married Dean. Having finally admitted they are separated, Richard and Emily formalize things by having Richard move into the pool house, with the girls splitting Friday nights between the two of ...
By season 5, Rory begins an affair with her first boyfriend Dean (Jared Padalecki) despite his unhappy teen marriage to Lindsay (Arielle Kebbel). While Rory attempts to call off their trysts via ...
In season five, Rory has an affair with her first boyfriend Dean (played by Jared Padalecki), who is married to Lindsay (played by Arielle Kebbel). ... Rory decides to call off the affair through ...
During season 4, Dean and Lindsay get married, with Rory later having an affair with Dean. While Gilmore Girls aired from 2000 to 2007 on The WB (with season 7 airing on The CW), ...
During the same period, Jess shows up unexpectedly at Yale to see Rory and asks her to run away with him, but she refuses. Dean gets jealous, but he and Rory grow closer and have an affair, during which Rory loses her virginity. Lorelai is angry and disappointed in Rory, who decides to leave for Europe with her grandmother for the summer to ...
Near the end of the trip, Lorelai and Rory reconcile over the phone, and Rory asks Lorelai to give Dean a letter for her. Dean's wife Lindsey finds the letter, which contains information about the affair. They consequently separate. Rory briefly progresses her relationship with Dean but it ends when he realizes how different their lives are.
Dean later marries Lindsay Lister (Arielle Kebbel) but maintains strong feelings for Rory, resulting in an affair before ending his marriage with Lindsay. Complications arise when Lorelai discovers the affair, causing temporary tension. Despite uncertainties about their future, Dean and Rory attempt to rekindle their romance, but differing life ...
Team Dean, Team Jess or Team Logan? "Gilmore Girls" fans have always debated the appeal of Rory Gilmore's (Alexis Bledel) three boyfriends. Kelly Bishop, who played Rory’s sophisticated and ...