As Rory rejoices after landing her dream job, Luke gets the residents of Stars Hollow together to throw Rory a grand graduation party. Emily and Richard are in attendance and listen teary-eyed with the rest of the guests as Rory gives a speech thanking Lorelai and everyone else for their support. Luke's thoughtfulness and kind gestures for Rory result in an unexpected reaction from Lorelai. Later, the morning that Rory leaves Stars Hollow, Luke opens the diner early for one last Gilmore girls diner breakfast before Rory heads out into the world as a political journalist.

The day before Rory’s graduation from Yale, Emily and Richard throw Rory a party and during which they perform a song in her honor. During the party, Lorelai and Christopher come face-to-face for the first time following their separation and thrilled to find that they can still be friends despite their recent rocky relationship. Logan makes a shocking move at the party when he asks Rory to marry him, but Rory, stunned and unable to give him an answer, turns to Lorelai to help her make a decision. Later, Rory and Paris graduate from Yale and Rory gives Logan an answer. Meanwhile, Lorelai and Luke’s relationship takes a step back when Luke overhears Lorelai saying that the karaoke serenade meant nothing.

With graduation rapidly approaching, Rory begins to become more and more stressed about her future. Lorelai tries to cheer her up by planning the perfect day of shopping and eating. Later, after seeing that Luke is once again wearing the blue baseball cap, Lorelai invites him to come with her and Rory to karaoke night at a nearby bar. After drinks, Lorelai sings an emotion-filled song, noticeably directed toward Luke. Meanwhile, Logan returns to Connecticut after a business trip in California and pays a visit to Lorelai to discuss his future plans with Rory.

Lorelai goes to Luke’s for breakfast for the first time since their engagement break-up, but they both soon find that it’s awkward to be around each other after everything that has happened. Later, when Lorelai’s Jeep dies, she has Luke help her shop for a new car. While at the dealership, Lorelai and Luke’s tension between one another mounts into a huge fight, which Lorelai takes as a good sign. Meanwhile, Paris, who has been accepted to dozens of law schools and medical schools, decides she has to break up with Doyle so their relationship doesn’t play a part in her decision as to which post-graduate program to attend. Finally, Rory receives a letter that will change her future plans.

As the citizens of Stars Hollow prepare for the annual Spring Fling festival, Rory decides to bring Logan home with her and takes him around the town. Lorelai, seeing how close the two have become, begins to worry that Logan’s immaturity and irresponsibility make him someone that Rory shouldn’t be with. Meanwhile, Taylor upsets the town when he blows the entire Spring Fling budget on a large hale bale maze. In the maze, Lorelai and Luke run into each other and there they admit that they each made mistakes that ultimately lead to the ending of their engagement as well as apologize for their actions. Lastly, Rory heads to an interview with the Providence Journal-Bulletin, but has a hard time making decisions that will affect not only her career, but the rest of her life.

Lorelai takes a road trip to North Carolina to attend Mia’s wedding, and after Rory has a fight with Logan over his immaturity, she agrees to go with. Emily invites herself on the road trip to get away from Richard, who is driving her crazy as he continues to recover from his heart attack. At the wedding, Emily becomes upset by how close Mia is with Lorelai and Rory. Later, Lorelai learns that Emily came to the inn several years ago to ask Mia for pictures of Lorelai and Rory from the years they weren’t speaking. Logan makes a surprise visit to the wedding to get Rory to forgive him. Meanwhile, Lane and Zach ask Luke to be the godfather to their twins. Finally, when Lane goes into labor, Luke helps get everyone to the hospital.

While planning a baby shower for Lane, Rory gets an unexpected call from the The New York Times offering her an interview. Rory scrambles to prepare for the interview leaving Lorelai to take over baby shower preparations. As Lorelai plans, she finds her self running interference between Lane and Mrs. Kim as they bicker over how Lane will raise the twins. Logan admits to Rory that his business venture went bad, and Rory offers him full support until Logan begins to revert back to his old ways by traveling to Las Vegas with Colin and Finn to blow off steam. Meanwhile, when Luke finds that Liz and T.J. are trying to sell his boat, he decides to make big changes in his life by taking April on a boat trip for the summer. Lastly, Lane is placed on bed rest and has to be wheeled in her bed across town to her party at Miss Patty’s.