5x01 “Say Goodbye to Daisy Miller" | September 21, 2004
Things are still tense between Lorelai and Rory. Emily announces that she and Richard have separated. Sookie is ecstatic to learn that Luke and Lorelai kissed. Dean provokes an argument with an unsuspecting Lindsay after his indiscretion with Rory. Emily decides to go to Europe and invites Rory to accompany her. Lorelai and Luke are very tentative with each other the day after until they are able to reassure each other that they're on the right path and Luke heads off to Maine for a week to help Liz and T.J. after an accident.

5x02 “A Messanger Nothing More" | September 28, 2004
T.J. is milking his injuries for all he's worth, but Luke decides that it's time to go home after seven weeks on the Renaissance Fair circuit. Rory calls to apologize and to ask her mother to deliver a letter to Dean. Sookie and Lorelai decide to decompress with a girls-day-out. Emily and Rory come home exhausted from fending off the attentions of randy European men. Lindsay finds Rory's letter and confronts Dean. Lane realizes that she's falling for Zack.

5x03 “Written in the Stars" | October 5, 2004
Luke and Lorelai enjoy their first official date where Luke tells her he's all in for their relationship, which is the basis for the next town hall meeting. Rory meets a rich Yale student named Logan and chews him out for being rude to her friend Marty. Paris holds a wake for Asher that all the guests assume is a keg party with a weird theme and Emily freaks out when she discovers that Richard has a social life she doesn't know about

5x04 "Tippecanoe and Taylor, Too" | October 12, 2004
Fed up with all the hoops Taylor makes Jackson go through, Jackson decides to run for town selectman with Lorelai and Sookie heading up the campaign only to find that he may not want the job after all. Rory and Dean try to work things out, but have trouble finding a place to be together. Lane confesses her true feelings to Zack.

5x05 “We Got Us Pippi Virgin" | October 19, 2004
Jackson is overwhelmed by the demands of his new job while Lorelai and Rory decide to see if they can get Richard and Emily back together. Lorelai decides that a double date with Rory and Dean is the way to smooth over the bumps in her relationship with Dean, but the evening goes awry when Luke can't get over feeling that Dean isn't good enough for Rory. Failing to get a response from Zach about the declaration of her feelings, Lane rescinds them, which finally gets Zach talking.

5x06 “Norman Miller, I’m Pregnant" | October 26, 2004
Rory, desperate for a story idea for the Yale paper, finally decides to research and write about a secret Yale society which happens to have connections to Logan. The Dragonfly Inn's accountant suggests dropping the lunch menu till the money situation improves, which has Sookie upset with the regularly lunching Norman Mailer, who only orders ice tea. With Luke and Lorelai hitting it off, Rory asks her dad to stay out of the picture. Sookie realizes she's pregnant again.

5x07 “You Jump, I Jump, Jack" | November 2, 2004
When Emily discovers that Lorelai is dating Luke, she insists he come to dinner. Not to be outdone, Richard invites Luke to a game of golf, and Luke finds himself overwhelmed by the strength of the elder Gilmores' personalities. After Zach announces that he's ready to start going out with Lane, they spend a cozy first date at home after banishing Brian to Lane's bedroom. Rory gets her story on the "Life and Death Brigade" by being blindfolded and whisked away by Logan and his friends to observe the elaborately staged weekend in the woods.

5x08 “The Party’s Over" | November 9, 2004
Luke tries to smooth things over with Liz and TJ when they stress out about buying a house in Stars Hollow. When Emily learns Rory and Dean are dating again, she calls a temporary truce with Richard to throw a party to introduce Rory to more suitable men. Dean realizes that he no longer fits into Rory's life, and Logan gallantly steps in to dry her tears.

5x09 “Emily Says Hello" | November 16, 2004
Jackson has his hands full between Sookie's food cravings and his town selectman duties. Emily decides to start dating again, and calls on a reluctant Lorelai for advice. Lorelai invites Christopher to lunch at the Inn and decides to surprise Rory by inviting her as well, but it's Lorelai who's surprised by the tension between father and daughter. Luke feigns indifference when Lorelai finally tells him about lunch with Christopher, but hints at some ambivalence during a later conversation with T.J.

5x10 “But Not as Cute as Pushkin”| November 30, 2004
Miss Patty celebrates forty years in show business on the same day that Luke mourns his father's death. Paris tries speed dating, where she hooks up with Doyle. Marty finally clues Rory in that both he and Logan are interested in her. Rory is asked to host a Chilton student for a few days at Yale, but the student is more interested in her freedoms than the responsibilities that go with them.

5x11 “Women of Questionable Morals" | January 25, 2005
Wanting to make peace with Rory, Christopher shows up at Yale, but she brushes off his attempt at compromise. When Lorelai learns that Christopher's father just died, she spends the evening at his place trying to comfort him, then disdains to tell Luke the truth about where she was. Emily & Richard are briefly reconciled when they find and take in a lost dog.

5x12 “Come Home" | February 1, 2005
After finding out that Emily started dating again, Richard's jealousy forces him to reconcile and they both agree to renew their wedding vows. Rory offers to help Logan write an article for the Yale Daily, but she is disappointed when he doesn't invite her to be his date at a book signing party thrown by his father. Emily warns Christopher that Lorelai and Luke are getting serious and he had better do something quickly if he hopes to end up with Lorelai.

5x13 “Wedding Bell Blues" | February 8, 2005
Emily and Richard renew their vows in front of their closest friends with Lorelai as Emily's Maid of Honor, and Rory as Richard's Best Man. Luke gets in a fight with Christopher over Lorelai. Logan comes to the ceremony with a girl, and Rory gets jealous. Rory confronts Logan and ends up kissing him.

5x14 “Say Something" | February 15, 2005
Lorelai does her best to get Luke to not give up on them after the awful events at the wedding but Luke tells her he needs some time. Rory asks Logan to hang out with her but is upset that when she gets to his place and discovers a lot of people there. Taylor has the whole town taking sides for either Luke or Lorelai. After taking care of her mom Rory goes back to Yale to work things out with Logan, making sure he understood that the hanging out didn't just mean hanging out.

5x15 “Jews and Chinese Food" | February 22, 2005
Lorelai is hurt again when she realizes Luke has moved his boat from her garage without even telling her. Meanwhile, Luke volunteers to build the sets for a school production of "Fiddler on the Roof", knowing that Lorelai is doing costumes, in hopes that their paths will cross. Rory tries to make up with Marty by hosting a movie night, but Logan interferes.

5x16 “So… Good Talk" | March 1, 2005
Luke, upset and missing Lorelai, begins to take it out on his customers. With the grandparents back from their second honeymoon Rory makes it clear that Friday night dinners are just dinner and nothing more. Emily acts like she doesn't realize all the hurt she's caused Lorelai, but goes to see Luke to make things right.

5x17 “Pulp Friction" | March 8, 2005
Rory and Logan's casual dating situation gets more complicated when Rory spots Logan with another girl and her jealousy sets in. Rory decides to go to a party with a guy she barely knows, which makes Logan jealous. Luke and Lorelai resolve things, but Lorelai is still upset with her mom and refuses to go to Friday night dinners, which makes Emily wonder if Luke followed through on their previous discussion.

5x18 “To Live and Let diorama" | April 19, 2005
Lorelai is interviewed by a magazine due to her success with the inn. Lane suspects Zach of cheating on her with Sophie. Lane, Paris and Rory commiserate about their love lives. Dean informs Luke that their situations are the same, and that Lorelai will eventually get bored and move on.

5x19 “But I’m a Gilmore!" | April 26, 2005
Luke's patience is tried as he takes over as temporary chef at the Dragonfly while pregnant Sookie is ordered to bed rest, but Sookie has trouble giving up control of her kitchen. Rory finally realizes that she's not a casual dater and tells Logan that she wants to be friends. He surprises her by suggesting they become a couple instead but his family isn't happy about the match. Paris learns the real reason why Doyle hasn’t returned her calls lately.

5x20 “How Many Kropogs to Cape Cod" | May 3, 2005
Lorelai meets to discuss selling the Dragonfly while Rory starts her new internship with Logan's father. Richard and Emily invite Logan to dinner, and Lorelai begs to attend but gets the cold shoulder.

5x21 “Blame Booze and Melville" | May 10, 2005
When the magazine article about the Dragonfly comes out, Luke and Lorelai get a little too enthusiastic when celebrating. Sookie goes into labor. Rory is given a surprising review by Logan’s father Mitchum and goes to extremes to unwind. Luke is upset when he finds out that Kirk has put in a competing offer on the same house.

5x22 “A House is Not a Home" | May 17, 2005
After receiving a call from Rory, Lorelai goes to pick her up from the police station. While on the way home Logan calls Rory and Lorelai orders her not to talk to him. Logan finds out that his father upset Rory and says he will have a talk with him, but Rory begs him not to. When Rory tells Lorelai that she won't be going back to Yale the following year, Lorelai, who doesn't like this idea, goes to her parents for help. Rory also goes to her grandparents to talk to them about her situation and ends up convincing them to support her. They then tell Lorelai that Rory will be living in their poolhouse until she decides she wants to go back to Yale. Meanwhile, Mrs. Kim helps Lane and her band get gigs and stay together.