Season 5 of the Gilmore Girls series was a very pivotal season due to the many changes that took place within the "year" that the show focused on. This was the season that Lorelei fell in love, Sookie found out she was pregnant again, and Rory made many life changes that altered the show entirely. Throughout this season, Rory grew as an individual person and severed some of the ties she had with her mother and began to bond more with her grandparents, family members that she previously had little contact with.

Season five started the season off in 2005 with an episode in which Lorelei and Rory argue over her affair with Dean, her long time high school boyfriend. The issue at hand was that Dean got married soon after Rory left for college. However, both Rory and Dean are still in love with each other. They wind up spending much of season five in an on again off again relationship since Lindsay, Dean's wife, has kicked him out after finding a letter that Rory wrote to Dean while she vacationing in Europe.

Season five is the season that Lorelei loses herself in love. This is the first that we see of Lorelei pursuing a relationship. There has always been a long standing tension between Luke and Lorelei, both obviously liking the other but nothing has ever been done about it. After five years, they decide to date. The entire town of Stars Hollow soon finds out about Luke and Lorelei's relationship when, after sleeping with each other, Lorelei goes down to the diner in Luke's shirt to find coffee and finds nothing more than a crowded diner full of townspeople.

A big portion of this season revolves around Rory getting situated with being at Yale. She meets Logan Huntzberger, a wealthy kid whose father happens to run a large paper. Having aspirations to become a journalist, Rory uses this connection to secure an internship. It is later found out that Mitch Huntzberger does not think that Rory is journalist material. This fact makes Rory very upset, and she ends up stealing a yacht to sail away on, which she ends up getting busted for.

At one point in the season, Rory tells Logan that she is not the casual dating type and that he has to commit or lose her. He makes the decision to date her seriously. Emily, Rory's grandmother is not impressed at all with Logan and says that he is not fit to date a Gilmore, while the Huntzberger family is anything less that pleasant to Rory when they meet her as well. Although Rory comes from a wealthy family, something very important to the Huntzberger's, she is not wealthy enough to date their son. It is then found out that the family actually has little to do with each other and spends most of their time apart.

Toward the end of this season, Lorelei becomes frenzied when she finds that Rory has stolen a yacht and she is going to be moving in with her grandparents. When she realizes that she could be losing her daughter and her best friend, she asks Luke to marry her. He is hesitant and the season is ended in suspense.