Set in the charming town of Stars Hollow, Connecticut, the series follows the captivating lives of Lorelai and Rory Gilmore, a mother/daughter pair who have a relationship most people only dream of.
Luke answers Lorelai's question and as news of Luke's reply leaks to the denizens of Stars Hollow, the untraditional proposal stirs up more talk than the answer itself. Richard and his lawyer go to bat for Rory in court for her yacht incident, but the judge is tougher than expected.
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.
Sookie creates a S'mores wedding cake, so what more does Lorelai need to set a date? Logan comes home, Lane and the band come home and Paul Anka eats three pounds of chocolate while under Luke's care.
After months of separation, Sookie tries to reconcile Rory and Lorelai by asking them to be the godmothers of her two children. However, they both end up fighting when Lorelai realizes that Rory didn't see fit to share her new cell phone number with her.
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.
After trying to figure out what Rory's future plans are by talking to Logan, Richard finally admits that he made a mistake by letting Rory drop out of Yale and comes to Lorelai to find a solution. However, Logan mistakenly thinks that Richard wants to know when they are planning to marry. Also, Rory makes a big declaration to Logan; Taylor gets busy in Stars Hollow when he decides to change all the street names back to their historic names. An idea which doesn't please Lorelai when she realizes what used to be the name of the street where the Dragonfly Inn is located.
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.
Rory is pleasantly surprised when her old flame Jess appears at her grandparents' house and reveals an amazing development in his life. Rory agrees to go to dinner with Jess, and 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
After a long absence, Christopher reappears in Lorelai and Rory's lives. Luke struggles with what the new person in his life will mean to him and his relationship with Lorelai. Lorelai and Rory enjoy their first Thanskgiving at the Dragonfly Inn, and Rory receives surprising news about Logan. Meanwhile, on the eve of an important gig for the band, Lane has to deal with Zach's jealousy over a song Brian wrote about her.
The perfect dress: elegant blush-silk tulle, in Lorelai's size and on sale -ideal for a wedding. The perfect mess: Lane, short tempered, belligerent and miserable since she broke up with Zach and moved back home.
Emily tells Lorelai that she'd like to get to know her future son-in-law better and asks her to invite Luke over for dinner - Lorelai purposely fails to mention that the wedding has been postponed... The Yale Daily News staff finally fires Paris and chooses Rory to be the new editor. A furious Paris kicks Rory out of the apartment, Logan subsequently convinces her to move into his place. Christopher tells Lorelai about Rory's new living arrangement.
As Valentine's Day approaches, Rory and Logan invite Lorelai and Luke to spend a weekend with them at Logan's family's house on Martha's Vineyard. Lorelai is upset by Luke's unfriendly attitude toward Logan. Luke's attitude changes when he realizes he forgot to buy Lorelai a Valentine gift, and Logan saves the day. When Lorelai finally confesses to Luke that she is worried the wedding will never take place, he reassures her that they will get married soon. The weekend ends in an ugly scene when Logan's father, Mitchum Huntzberger arrives.
Lorelai offers to help Christopher out by babysitting his 4-year-old daughter, G.G, and is horrified by the toddler's terrible behavior. The next day, Rory and Logan attend the wedding of Logan's sister, Honor. While helping the bride and her three bridesmaids get ready, Rory is devastated to learn how Logan spent his time during their recent breakup.
Rory forgives Logan, then needs some time for herself, so she pays a visit to Lorelai in Stars Hollow. Although Lorelai refuses to admit that she is upset, Rory can tell that she is bothered by the news that Luke will be gone for a few days on a field trip with his daughter, April. And, against Lorelai's wishes, Rory pays a visit to the store owned by April's mother, Ana, to spy on her. Meanwhile, when Zack finally works up the courage to ask Mrs. Kim for permission to marry Lane, he is surprised at the deal she makes with him.
Although Rory and Logan are back together, Logan is miserable knowing that Rory hasn't really forgiven him, and he takes off with his friends for another stunt with the Life and Death Brigade. Rory accepts Jess's invitation to attend an open house at his new book store/art gallery/publishing house in Philadelphia. While there, she is surprised to run into Luke, who is accompanying his daughter April on an academic field trip.
Lane and Zack's wedding is coming up and since Luke is busy, Michel is Lorelai's first choice as a date for Lane and Zack's wedding, but he gets Celine Dion tickets and bails. Rory suggests that Chris go as Lorelai's date and Chris is totally psyched to do it. Grandma Kim is a Buddhist and doesn't know that Mrs. Kim is a 7th Day Adventist. At Lane's wedding, Lorelai collapses and Christopher is there to take care of her.
Logan comes home from the hospital and is cared for by an overprotective Rory; Liz has big news for Luke; Emily has LASIK eye surgery, so Lorelai has to serve as her chauffeur; Rory is upset by a statement Logan's dad made about her in an interview in the Wall Street Journal; Jackson discovers that former employees planted marijuana in one of his fields, and he and Sookie try to dispose of it.
Stars Hollow needs a new town troubadour and there are many hopeful people trying out, much to Taylor's dislike. Lorelai finally confronts Luke about their long engagement and Rory and Logan spend their last night together before he must go to London.
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