Thirty something Lorelai Gilmore (series star LAUREN GRAHAM) and coffee shop owner Luke Danes (series star SCOTT PATTERSON) begin making plans for their future, but Luke is embarrassed when word spreads that Lorelai was the one who proposed marriage. Still hurt that her daughter, Rory (series star ALEXIS BLEDEL), has decided to drop out of Yale and move in with Lorelai's proper, old-money parents, Emily (series star KELLY BISHOP) and Richard (series star EDWARD HERRMANN), Lorelai tells them that they can take care of Rory from now on. Although Richard hires a respected attorney and longtime friend to help Rory get an easy sentence for stealing the yacht, a judge orders Rory to serve 300 hours of community service. Rory's boyfriend from Yale, Logan Huntzberger (series star MATT CZUCHRY), hosts a "felon party" for Rory.

Rory begins to work her 300 hours of community service and finds that life on a road crew is not pretty. Lorelai and Luke try to decide whether they will fix up Lorelai's home or buy the Twickham house, which Luke has always admired. Luke's sister, Liz (recurring guest star KATHLEEN WILHOITE - "ER"), begs him to hire her husband, T.J. (recurring guest star MICHAEL DeLUISE - "NYPD Blue"), as a contractor. When Rory surprises Luke with a visit at the diner to find out how Lorelai is, he feels obligated to tell her that he and Lorelai are engaged. Afterwards, Luke confronts Lorelai about her estrangement from Rory. Feeling lonely, Lorelai adopts a dog at the Stars Hollow pet fair. Finally, during a chance meeting, Lorelai and Rory have an angry confrontation about their mutual hurt feelings.

Excited to cater Lorelai's wedding, Sookie pressures Lorelai to set a date but cannot get her to commit. While completing her community service hours, Rory takes a job at Emily's DAR (Daughters of the American Revolution) office. Convinced that she has a rival for the job of DAR president, Emily uses Rory as her spy. Logan returns from Europe and goes back to Yale, forcing Rory to confront her true feelings about quitting college. Lane and her band come home after spending their summer performing out of town. Luke agrees to take care of Lorelai's dog, Paul Anka, while she works late at the inn and ends up rushing the dog to the vet. Finally, Lorelai admits to Luke her reason for putting off their wedding.

Lorelai misses Rory and tries to call her but soon discovers that her daughter's cell phone is no longer in service. Sookie asks Lorelai and Rory to be the godparents to her two children, hoping they will reconcile when they see each other at the ceremony. However, mother and daughter end up fighting when Lorelai realizes that Rory gave her new cell number to Sookie but not to her. Logan learns that his father expects him to graduate this year and enter the family business. Wanting to break free from family pressures, Logan whisks Rory off to a weekend in New York.

Rory does a fabulous job organizing a big DAR bash for Emily. However, at the party, Richard confronts Logan's father, Mitchum Huntzberger (recurring guest star GREGG HENRY - "Eyes," "Payback"), about his opinion of Rory's journalistic talents, while Emily has an even uglier confrontation with Logan's mother, Shria (LEANN HUNLEY - "Dawson's Creek"), over the romance between Rory and Logan. Meanwhile, after a small kitchen fire at the Dragonfly Inn, Lorelai enlists Richard's help in settling the insurance claim. She also needles him about the fact that he has been unable to get Rory to return to Yale. Although he's annoyed with Lorelai, Richard admits that Rory is not doing what she should be doing.

Richard tries to gather information from Logan about Rory's future plans, but Logan mistakenly thinks that Richard is asking when he plans to marry Rory. Lorelai supports Taylor's (recurring guest star MICHAEL WINTERS) plan to change all the Stars Hollow street names back to their original historic ones, until she learns the disgusting former name of the street on which the Dragonfly Inn is located. Rory makes a surprising confession to Logan. Richard finally admits that he should have never allowed Rory to drop out of Yale and shows up at Lorelai's house to discuss the matter.

As Rory's 21st birthday approaches, both Lorelai and Rory are saddened that their estrangement will keep them from spending the day the way they had always planned. Richard tries to convince Lorelai to help him concoct a plan to get Rory to return to Yale, but Lorelai insists that Rory has to make the decision herself. Meanwhile, Emily plans an elaborate birthday party. Later, Emily and Richard are shocked when they realize that Rory and Logan have been having sex. Former Secretary of State MADELEINE ALBRIGHT appears in a cameo role as herself.

Rory is pleasantly surprised when her former boyfriend Jess (recurring guest star MILO VENTIMIGLIA - "The Bedford Diaries") appears at her grandparents' house and reveals an amazing development in his life. Rory agrees to go to dinner with Jess, but when Logan unexpectedly joins them, an ugly confrontation develops, leaving both Rory and Logan to face the choices they have made. Emily is concerned about Rory's sudden evasiveness and tries to exert some parental discipline. Meanwhile, Luke agrees to sponsor a local girls' soccer team, and Lorelai channels all her concerns about Rory into caring for her dog, Paul Anka.

A surprise phone call from Rory's dad illuminates issues of trust between Lorelai and Luke. Later, when a person from his past shows up in Stars Hollow, Luke has no idea how to tell Lorelai. After months of estrangement, Lorelai and Rory make their first move towards reconciliation, and Rory takes major steps to change the direction of her life.