The fifth season of Gilmore Girls, an American comedy drama television series, began airing on September 21, 2004, on The WB.

Dean's marriage to Lindsay comes to an abrupt end when she finds a letter Rory wrote to him about their night together.

Lane is shocked to realize she has feelings for Zach and they start dating, but she surprises them both by revealing she wants to wait for marriage before having sex.

Despite romantic overtures from Marty, Rory is drawn to Logan Huntzberger, a rich playboy who introduces her to a hedonistic thrill-seeking lifestyle.

Lorelai refuses to let her come home so Richard and Emily let her move into the pool house and get a job, hoping she will change her mind.

Luke tells Taylor he is pulling out of the house purchase when he discovers Lorelai is considering selling the inn, while Lane's mother arranges for her and the band to tour church theaters.