<P> Lorelai accepts Max's proposal, but realises shortly before the wedding that it isn't right and they break up . She and Sookie get excited about opening their own business at the dilapidated Dragonfly Inn but the owner refuses to sell . Sookie gets engaged to Jackson Belleville, a local farmer . Luke's teenage nephew, Jess Mariano, comes to live under his care . Jess is sullen and angry with everyone apart from Rory . The two strike up a friendship, causing jealousy in Dean . Lorelai is disapproving, especially when they are in a car accident, which leads to a blow - up with Luke . Richard announces that he has retired but soon becomes bored and sets up his own insurance company . Christopher appears to have his life together and Lorelai decides to reunite with him . But at Sookie's wedding Christopher learns that his recently estranged fiancé is pregnant and decides to return to her, leaving Lorelai heartbroken . At the same time, Rory impulsively kisses Jess . </P> <P> Rory's attraction to Jess grows stronger, and she gets jealous when he teases her with a new girlfriend . Dean can't ignore what is going on, and eventually ends their relationship . Rory and Jess immediately become a couple . Meanwhile, she and Paris spend the year as Student Body Presidents at Chilton and both submit applications to Harvard University . Paris is devastated when she doesn't get in . Rory is accepted but decides to attend Yale University instead, much to Emily and Richard's delight . The Independence Inn is badly damaged in a fire, but Lorelai and Sookie are able to buy the Dragonfly when its elderly owner dies . Jess tries to force Rory to have sex with him, which lead to a fight between Dean and Jess . Luke begins dating a lawyer named Nicole . Lane Kim, Rory's best friend, starts a band called Hep Alien and tries to convince her strict mother to let her date the guitarist, Dave, while keeping the band secret . As the season ends, Jess abruptly leaves Stars Hollow to track down his estranged father in California, and Rory graduates High School as valedictorian . </P> <P> Rory starts her college education at Yale, with Paris - now a friend - as her roommate . Both start working for the Yale Daily News . Rory is surprised when Dean quickly marries his new girlfriend . The pair grow closer again over the season, leading Rory to turn down Jess when he returns and declares his love . Lorelai spends the season renovating the Dragonfly Inn in preparation for its open, along with Sookie and their colleague Michel . She also begins a relationship with Richard's new business partner, Jason Stiles, which she keeps secret from her parents . Lane's mother learns about Hep Alien and throws her out of the house . Sookie and Jackson have a son . Emily feels neglected by Richard and the two separate, with Richard moving into the poolhouse . Luke and Nicole elope during a cruise, but quickly decide to divorce . Towards the end of the season, Luke accepts that he is in love with Lorelai and begins wooing her . The pair finally kiss on the Dragonfly's opening night, while Rory loses her virginity to a married Dean . </P> <P> Lorelai and Luke start a relationship . Emily and Richard - who reunite and renew their wedding vows - disapprove, and Emily interferes by telling Christopher to try and win her back . Luke feels overwhelmed, resulting in a brief separation between him and Lorelai and a rift between Lorelai and Emily . Rory tries to have another relationship with Dean, now separated from his wife, but it soon ends when he realizes how different their lives are . She falls for Logan Huntzberger, a wealthy playboy Yale student whose parents think she is beneath him . Lane and Paris both start relationships: the former with her bandmate Zack, the latter with Yale Daily News editor Doyle . Sookie has a daughter . Rory gets an internship at Logan's father's newspaper but is deflated when he tells her she "doesn't have it ." She and Logan are arrested for stealing a yacht, after which Rory announces that she is quitting Yale and moves in with Emily and Richard . When Lorelai sees how supportive Luke is over the situation, she asks him to marry her . </P>

Who does rory have her first time with