Rory and Dean

Rory meets Dean Foresterin the first episode of the series. Rory learns that Dean is interested in her as he first approaches her by telling her that he has been "watching her." Rory helps him attain a job at Doose's Market. Rory shares her first kiss with Dean after he offers her a soda, then kisses her. He escorts Rory to a dance after which they finalize their official dating status. After a long night, they fall asleep in Miss Patty's studio. When Lorelai finds out that they were together all night she is angry at the possibility of a recurrence of her own indiscretion, making her resent Dean. After she gets to know him, she ends up really liking him. Rory maintains a relationship with Dean for almost two and a half years. He breaks up with her briefly in the first season, when she isn't able to reciprocate his statement, "I love you." In the season one finale Rory finally admits to Dean that she too loves him. Eventually, Rory renews her relationship with Dean and they remain a steady couple until the third season, when Dean decides to call it quits because he is convinced that Rory is in love with Jess Mariano, Luke Danes's nephew. They do not reunite until much later, when she loses her virginity to a now-married Dean in an unexpected fling, which ultimately ends his marriage and creates a short-lived rift between her and her mother. Rory and Dean break up when he decides he can't compete with her life at Yale and her new Yale friends including Logan Huntzberger.