: The season features the series' milestone 100th episode, "Wedding Bell Blues," where Richard and Emily renew their vows and a major confrontation occurs between Luke and Christopher.

In Season 5 of Gilmore Girls , a prominent feature is the , which begins in the season premiere, "Say Goodbye to Daisy Miller". Additional key features of this season include:

: Rory begins dating Logan Huntzberger, a wealthy heir and member of Yale's elite "Life and Death Brigade," marking a major shift in her social circle.

: For those with the physical Gilmore Girls: Season 5 collection, the set includes an audio commentary for the 100th episode by creators Amy Sherman-Palladino and Daniel Palladino, as well as a documentary titled The Gilmore Girls Turn 100 .

: The season concludes with a massive fallout between the mother-daughter duo after Rory decides to drop out of Yale and move into her grandparents' pool house—a storyline often cited by fans as one of the show's most controversial.

: The season begins with the Gilmore elders separated and living apart, leading to a temporary change in the family's Friday night dinner dynamic.