Jason's father, Floyd (LAWRENCE PRESSMAN - "American Pie" movies), sues Jason and Richard for taking his clients. Floyd also reveals that Jason and Lorelai have been dating secretly for months. Meanwhile, Dean (former series star JARED PADALECKI) upsets Rory when he admits he has dropped out of college to work full time so he and his wife, Lindsay (recurring guest star ARIELLE KEBBEL), can buy a townhouse. Lindsay demands that Dean stop associating with Rory, but Dean and Rory plan to secretly remain in contact.
When Jason reveals that he is no longer in business with Richard, Lorelai has an ugly confrontation with her father about his treatment of Jason. Later, after an extremely uncomfortable Friday night family dinner, Lorelai and Rory spy on Emily and make a shocking discovery about the state of the elder Gilmores' marriage. Meanwhile, Luke tells Lorelai that he and Nicole are getting a divorce.
Depressed over the failure of his marriage, Luke resorts to a self-help tape and suddenly realizes that he already knows who his soul mate is. Later, when his sister Liz (recurring guest star KATHLEEN WILHOITE) returns to town and announces that she and T.J. (MICHAEL DeLUISE) are getting married, Luke finds Jess (former series star MILO VENTIMIGLIA) and convinces him to attend the wedding. Meanwhile, Lorelai is completely stressed as opening day at The Dragonfly Inn approaches, and Rory pretends not to be interested when Lorelai tells her she overheard Dean (former series star JARED PADALECKI) and his wife, Lindsay (recurring guest star ARIELLE KEBBEL), fighting.
All the townspeople of Stars Hollow come to Liz's (recurring guest star KATHLEEN WILHOITE) Renaissance-themed wedding. Jess (former series star MILO VENTIMIGLIA) walks Liz down the aisle, and Lorelai and Luke share a romantic dance, after which Luke asks Lorelai out on a date. Meanwhile, as Yale students begin their summer break, Rory attends a drunken party and has to call Dean (former series star JARED PADALECKI) to drive her back to the dorm. Dean tries to explain his unhappy marriage to Rory, but they are interrupted when Jess arrives and makes Rory a surprising offer.
Lorelai suspects that Luke's intentions towards her have become serious, but she doesn't have time to dwell on the situation as she prepares for the opening of the Dragonfly Inn by inviting friends and family to a test run. Using the opportunity to force her parents to reconcile, Lorelai is shocked when it becomes obvious that the damage to their marriage is greater than she had thought. When Jason arrives at the Inn to convince Lorelai that their own breakup was a mistake, Luke tries to declare his true feelings for Lorelai. Meanwhile, after their last awkward encounter, Rory attempts to salvage her friendship with Dean (former series star JARED PADALECKI).
After 19-year-old Rory Gilmore (series star ALEXIS BLEDEL) makes love with her former boyfriend, Dean (recurring guest star JARED PADALECKI)--who is married--she argues bitterly with Lorelai (series star LAUREN GRAHAM), who is disappointed by her daughter's choices. Despite her best efforts, Rory cannot resist Dean, even when she guiltily observes how hard Dean's eager young wife is working to keep their marriage together. Meanwhile, Lorelai copes with a tricky situation of her own: Eccentric resident Kirk (series star SEAN GUNN) has witnessed her kissing recently divorced coffee shop owner Luke Danes (series star SCOTT PATTERSON) after the gala opening of the new Dragonfly Inn, Lorelai's long-awaited venture with her friend Sookie St. James (series star MELISSA McCARTHY). Despite the gossip, Luke and Lorelai seem to finally be happy together. The longtime marriage of Lorelai's parents, Richard and Emily (series star KELLY BISHOP), continues to crumble.
While calling Lorelai from Rome, Rory admits that she complicated her relationship with Dean (recurring guest star JARED PADALECKI). Lorelai gives Dean a letter from Rory, but Dean's wife, Lindsay (recurring guest star ARIELLE KEBBEL), finds the letter and makes Dean move out of the house. Rory returns from Europe, and a terrible argument ensues when she and Lorelai encounter Lindsay and her mother. Meanwhile, Luke returns to Stars Hollow after spending several weeks helping his injured sister, Liz (recurring guest star KATHLEEN WILHOITE), on the Renaissance Fair circuit. Luke and Lorelai try to find a private spot to say hello but are interrupted by a town parade.
Early in the morning after Lorelai and Luke spend a romantic night together at Luke's place, Lorelai walks into the diner dressed in one of Luke's flannel shirts and discovers that the place is full of customers. Lorelai is a little offended when it appears that no one cares about their relationship--until it becomes a topic of heated discussion at the town meeting. Meanwhile, Rory verbally spars with a haughty, rich student named Logan (recurring guest star MATT CZUCHRY - "Eight Legged Freaks") after he is rude to her friend Marty (recurring guest star WAYNE WILCOX). And Paris holds a wake for her older lover Professor Asher Flemming, who died over the summer.
Rory and Dean have difficulty meeting alone because they live far apart and Dean (recurring guest star JARED PADALECKI) shares a car with his estranged wife. Impulsively, Rory asks Dean if he left his wife because Lindsay found Rory's letter--and she is not completely satisfied with his response. Lorelai and Sookie manage Jackson's (recurring guest star JACKSON DOUGLAS) campaign when he decides to compete against Taylor (recurring guest star MICHAEL WINTERS) for town selectman. Lane tells her band mate Zach (recurring guest star TODD LOWE) that she has feelings for him.
Feeling bad that her relationship with Dean (recurring guest star JARED PADALECKI) has become awkward, Lorelai suggests that she and Luke go on a double date with Rory and Dean. But Lorelai's plans go awry when Luke is unable to disguise the fact that he thinks Dean isn't good enough for Rory. Meanwhile, Emily and Richard are lonely and a little lost without each other, but neither one can take the first step toward reconciliation.
Lorelai and Sookie are thrilled when author NORMAN MAILER (himself) and a young reporter, Josh Davies (STEPHEN MAILER, Norman's real-life son), show up repeatedly in the dining room of the Dragonfly Inn, but Sookie's awe turns to annoyance when Mailer refuses to order any food. Working on a story for the Yale newspaper, Rory uncovers evidence of an intriguing secret society to which Logan (recurring guest star MATT CZUCHRY) belongs. Meanwhile, when Rory's father, Christopher (recurring guest star DAVID SUTCLIFFE - "I'm With Her"), appeals to Lorelai for help after his girlfriend leaves him to raise their baby daughter by himself, Rory orders him to leave Lorelai alone. Finally, Sookie realizes that she is pregnant again.
Lauren Graham
Lorelai Gilmore
Alexis Bledel
Rory Gilmore
Melissa McCarthy
Sookie St. James
Keiko Agena
Lane Kim
Yanic Truesdale
Michel Gerard