Richard, who has become increasingly irritable and contentious with Emily, begins to put in more hours in the office than ever. Without telling Emily, he cancels several important social engagements due to the pressures of work, which leaves her both upset and concerned about her husband. At the urging of her friends, she decides that Rory's making her debut at a society ball will be just the thing to get Richard back into the social swing. To Lorelai's amazement, Rory willingly agrees and Emily goes into high gear shopping in preparation.

Dean protests loudly about the formal attire he is forced to wear and the fox-trot lessons he is forced to take from Miss Patty, so Rory promises him a lifetime of watching Battle Bots at his side if he'll be a good sport and go along with the occasion.

Lorelai asks Christopher to escort their daughter on the night of the big event, and he surprises her by agreeing to come willingly. Lorelai is in for even more of a shock when he arrives on time, dr

Feeling a little lonely, Lorelai adopts a dog. Luke agrees to repair Lorelai's house, rather than buy the Twykham house. This soon turns into trouble as TJ does some unwanted construction on the house. Rory starts her community service assignment. Feeling neglected and unhappy with how things are going, Rory visits Luke at his diner. He lets it slip that he and Lorelai are engaged, leaving Rory feeling even more alone.

Lorelai needs Richard's help with her insurance after a small fire at the Dragonfly Inn and uses the occasion to talk to him about the fact that he didn't manage to get Rory back into Yale. Although he doesn't appreciate Lorelai's reprimand, Richard has to admit that Rory is not where she should be.

Meanwhile, Rory organizes a fabulous D.A.R. party for Emily but the evening doesn't turn out so well when Richard confronts Mitchum Huntzberger, Logan's father, about his opinion on Rory's journalistic talents.

Lorelai refuses to listen to Richard's plan to bribe Rory into resuming school, saying that Rory has to want to go back on her own. Both Rory and Lorelai are saddened by the fact that their estrangement is keeping them apart on Rory's 21st birthday. Emily takes it upon herself to plan a party for her granddaughter when Rory shows no interest in the event. Richard and Emily find out that Rory and Logan have been sleeping together. Lorelai tries to convince Luke to participate in her mad scientist Halloween skit.

At Rory's graduation party at her grandparent's house, Logan proposes to her. Emily and Richard sing Rory a graduation song. Rory is caught off-guard and says she needs time to think about it. After Rory graduates from Yale, she tells Logan that she can't marry him. Logan tells her it's all or nothing and Rory decides to decline. Logan ends their relationship.