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Rory is pleasantly surprised when her former boyfriend Jess 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.
After a long absence, Christopher Haden, Rory's father, reappears in the lives of Lorelai and Rory. Luke struggles with what the presence of Christopher will mean to him and his relationship with Lorelai. Lorelai and Rory enjoy their first Thanksgiving 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 Zack's jealousy over a song Brian wrote about her.
Feeling that he has missed too much and wants to get to know his newly discovered daughter, Luke goes to have a talk with her mother, his former girlfriend Anna Nardini. Meanwhile, Lorelai sets a date for the wedding after finding the perfect dress, but she is worried by the nagging feeling that something is about to go wrong. Back at Yale, Rory happily moves into a dingy off-campus apartment with Paris and Doyle tries to avoid running into Logan. However, when Logan shows up at her apartment and declares his love for her, Rory breaks down.
Knowing he has let too much time go by, Luke is still unable to tell Lorelai about the existence of his 12-year-old daughter, April, and he is thrown into a panic when April wants to hang out with him at the diner. When April and Lorelai both show up at the diner and begin chatting, April innocently explains that Luke is her father. Lorelai tries to be supportive, even offering to postpone the wedding date, but Luke's reaction to this idea leaves her confused and hurt. Back at Yale, Logan takes unusual steps to win Rory back, and the newspaper staff rebels against Paris' reign of terror at the Yale Daily News. Meanwhile, Stars Hollow holds its annual Winter Carnival, and Lorelai and Rory run a booth featuring their dog, Paul Anka, as a fortuneteller.
While Luke deals with the reality of having his daughter, April, in his life, Lorelai tries to pretend she doesn't mind the repercussions the new situation is having on their engagement. Rory's concern over Paris' lack of management skills at the Yale Daily News finally reaches a crisis point when most of the staff quits in protest. With Logan's help, Rory makes a valiant attempt to get the paper out on time. Meanwhile, Lorelai breaks the news to Richard and Emily that their money will no longer be needed for Rory's education, and the resentment starts to build. The subsequent Friday night dinner erupts into an emotional confrontation where all four Gilmores finally get their issues out on the table.
Wanting to get to know her future son-in-law better, Emily asks Lorelai to invite Luke over for dinner. In order to avoid an argument, Lorelai purposely fails to mention that the wedding has been postponed. Meanwhile, the Yale Daily News staff finally fires Paris and chooses Rory to be the new editor. After a furious Paris kicks Rory out of the apartment, Rory has no idea where to go until Logan convinces her to move into his apartment. When Rory gives Christopher a tour of Yale, he learns of the new living arrangement and tells Lorelai.
As Valentine's Day approaches, Rory and Logan invite Lorelai and Luke to spend a weekend with them at Logan's family house on Martha's Vineyard. Rory and Logan have a wonderful time, but Lorelai is upset by Luke's unfriendly attitude towards Logan. Luke's attitude changes when he realizes he forgot to buy Lorelai a Valentine gift, and Logan saves the day by letting Luke give Lorelai one of the gifts he had bought for Rory. 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 and berates Logan for ignoring his responsibilities in the family business.
Proud parents Lorelai and Christopher attend a journalism panel at Yale, where Rory dazzles the crowd. Afterwards, Lorelai offers to help Christopher by baby-sitting his 4-year-old daughter 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. Logan tries to defend his actions, but a devastated Rory turns to Lorelai and Paris for comfort. Also, Lane is still heartbroken over Zach--until he turns up at the diner with a surprise.
After forgiving Logan for his indiscretions, Rory needs some time for herself, so she visits 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. Against Lorelai's wishes, Rory goes to the store owned by the girl'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.
Lorelai has a bizarre dream about singer/songwriter Paul Anka (himself). Meanwhile, 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' 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. Back in Stars Hollow, Lorelai is horrified to find that Richard and Emily have been looking at real estate in her town.
On the night before Lane and Zach get married, Lorelai and Rory's plans for a bachelorette party go awry, as do the plans made by Zach's buddies, so the two groups end up together for a makeshift party in a vacant parking lot. Meanwhile, Mrs. Kim tells Lorelai to bring an escort to the wedding. Since Luke is still out of town, Lorelai invites Christopher to be her date. Everyone attends two wedding ceremonies--one Buddhist and one Seventh Day Adventist--followed by a wild wedding reception in the town square.
When Luke prepares a birthday party for April at the diner, Lorelai volunteers to help but is hurt after Luke explains that he still thinks it's too soon for April and Lorelai to meet. Luke changes his mind, however, when the party is a disaster, giving Lorelai a chance to bond with April while turning the event into a huge success. Meanwhile, Rory rushes to be with Logan at the hospital after he is seriously injured during a stunt with the Life and Death Brigade.
Temporarily unable to see after minor eye surgery, Emily enlists Lorelai's help as her driver and companion, finally revealing a surprise that catches Lorelai completely off guard. Meanwhile, Rory takes charge of Logan's recovery when he is released from the hospital. And Luke helps his sister Liz and her husband, T.J., deal with Liz's pregnancy.
On the evening of Logan's graduation from Yale, Rory throws him a wild party, but the knowledge that he is being forced to leave for London the next day makes their time together bittersweet. Meanwhile, at a Friday night dinner, Emily and Richard attempt to introduce Christopher to an attractive young woman. And realizing that she was wrong to let Luke postpone their wedding for so long, Lorelai delivers an ultimatum. Also, Stars Hollow is suddenly overrun with musicians when news gets out that the town's regular street performer, the Town Troubadour, has been 'discovered.' SONIC YOUTH, SAM PHILLIPS, MARY LYNN RAJSKUB, YO LA TENGO, SPARKS, JOE PERNICE and DAVE GRUBER ALLEN perform.
Lorelai wakes up in bed with Christopher. Confused and mortified, she makes a hasty exit, ignoring Christopher's pleas that she stay. Once at home, Lorelai tries to get rid of everything that reminds her of Luke and ends up practically emptying her house. Rory receives a toy rocket ship as a parting gift from Logan and is baffled as to its meaning.
Rory is upset over Logan's absence and the fact that they had to cancel their long-planned trip to Asia. Wanting to cheer Rory up and distract herself from her own sad love life, Lorelai turns her house into an Asian-themed wonderland. Lane returns from her disastrous honeymoon. While repairing the damage to the diner, Luke tells his brother-in-law, T.J., about his breakup with Lorelai, prompting T.J. and Luke's sister, Liz, to insist that Luke come over for dinner and sympathy. When Luke and Lorelai run into each other in town, Luke can't hide his anger over their breakup. And Rory is furious when she learns that Lorelai slept with Christopher.
When Richard and Emily display no real reaction to the news of her breakup with Luke, Lorelai realizes that most of her emotional life has been based on doing and feeling the opposite of whatever her parents want. Later, when Michel forces Lorelai to attend Emily's beautiful cotillion dance, Lorelai discovers that some things her parents wanted for her weren't really that terrible. Meanwhile, Rory has a tough time making her long-distance relationship with Logan work. And after taking Rory out for a father/daughter dinner, Christopher makes a startling confession to Lorelai.
Lorelai and Christopher have resumed their relationship, and although Lorelai is finding it difficult to fully commit to him, Christopher keeps coming up with romantic dates to win her over. Meanwhile, at Yale, Rory meets some eccentric new girlfriends at an art exhibit, and Richard becomes a guest lecturer. Also, April comes to stay with Luke for a few weeks while her mother, Ana, is out of town. And when Emily gets arrested, Lorelai must bail her out of jail.
Emily and Richard are delighted when Lorelai and Christopher attend Friday night dinner together as a couple. After Christopher reveals that his ex-wife, who lives in Paris, wants him to send their daughter, G.G., there for a visit, Lorelai argues with him over dinner. Meanwhile, in town on business to acquire an Internet company, Logan visits the surprised Rory. Although she is thrilled, Rory realizes during a dinner with Logan's colleagues that she has no connection to his new business world--and she is especially threatened by one of his beautiful co-workers. Also, Stars Hollow is plagued by a terrible odor when a train with a full load of pickles derails, and Taylor refuses to pay for the cleanup.
After Christopher persuades Lorelai to visit Rory at Yale during Parents' Weekend, Lorelai is surprised to find that Richard and Emily are also there. Trying to impress Rory's co-workers at the Yale Daily News, Christopher invites them to an expensive lunch, where they all drink too much. The meal ends abruptly when Rory insists that everyone has to leave and cover a breaking story. Meanwhile, Luke meets April's swimming coach, who convinces him to take her adult swimming class. When the coach flirts with him, Luke asks her out on a date.
Christopher and Lorelai take his daughter, G.G., to visit G.G.'s mother in Paris. Despite severe jet lag, Christopher and Lorelai manage to have a wonderful, romantic time enjoying the city and each other. Back in Connecticut, Rory comes to the end of her tenure as editor in chief of the Yale Daily News and suddenly finds herself unsure of her future. Her new friends Olivia and Lucy suggest a trip to Stars Hollow for a girls' night while Lorelai is out of town. Upon returning, Rory is surprised to find that Lucy's new boyfriend is Rory's old friend Marty, who pretends not to know Rory. And later, Christopher and Lorelai return home with a surprise for everyone.
After Lorelai invites Rory to dinner and tells her that she and Christopher got married in Paris, Rory pretends to be thrilled while Christopher is in the room. But she later tells Lorelai how hurt and angry she really is. Meanwhile, back in town for the startup of his new Internet company, Logan invites Rory to the launch party, where she meets a magazine editor who suggests that she write an article on the event. But when Rory writes a judgmental article, describing the guests as spoiled elitists, Logan accuses Rory of hypocrisy, considering she is living rent-free in his apartment. Defensive at first, Rory eventually realizes that she is living a double standard and decides to find her own apartment. Meanwhile, when April faces a medical emergency, Luke frantically turns to Lorelai for help.
When Christopher asks Lorelai why she has avoided involving him in the daily life of Stars Hollow, she admits that she is concerned her old friends will not accept him. In an effort to help him bond with the townspeople, Lorelai brings Christopher to the town knit-a-thon, where his well-intentioned gesture brings the event to an early end. Meanwhile, when Olivia hosts a 2002-themed birthday party for Lucy, Rory gets a chance to confront Marty about his coldness toward her. Also, Luke is touched by the birth of Liz and T.J.'s baby, and when he learns that Anna is planning to move to New Mexico with April, he demands equal rights as a parent of April.
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