<Li> Marion Ross as Lorelai' Trix' Gilmore the First </Li> <Li> David Sutcliffe as Christopher Hayden </Li> <Table> <Tr> <Th> No . overall </Th> <Th> No. in season </Th> <Th> Title </Th> <Th> Directed by </Th> <Th> Written by </Th> <Th> Original air date </Th> <Th> Prod . code </Th> <Th> US viewers (millions) </Th> </Tr> <Tr> <Th> 44 </Th> <Td> </Td> <Td> "Those Lazy - Hazy - Crazy Days" </Td> <Td> Amy Sherman - Palladino </Td> <Td> Amy Sherman - Palladino </Td> <Td> September 24, 2002 (2002 - 09 - 24) </Td> <Td> 175001 </Td> <Td> 5.7 </Td> </Tr> <Tr> <Td_colspan="8"> Amidst her sadness about Christopher, Lorelai has an intriguing dream about Luke . Rory returns from Washington to realize that she still may have feelings for Jess, but a chance encounter at the First Annual Stars Hollow End of Summer Madness Festival makes her realize that he may have moved on to someone else . Relationship quarrels abound--Sookie and Jackson over decorating their house, Lorelai and Rory over Jess versus Dean, Emily and Richard over Lorelai and Christopher--but are on the path to resolution . Rory once again guides Paris through the rocky shoals of preparing for a date . </Td> </Tr> <Tr> <Th> 45 </Th> <Td> </Td> <Td> "Haunted Leg" </Td> <Td> Chris Long </Td> <Td> Amy Sherman - Palladino </Td> <Td> October 1, 2002 (2002 - 10 - 01) </Td> <Td> 175002 </Td> <Td> 5.8 </Td> </Tr> <Tr> <Td_colspan="8"> To Lorelai's horror, Kirk asks her out on a date after being encouraged by Luke . Emily's lunch with Lorelai at Luke's ends badly . Christopher shows up uninvited at Friday night dinner and quarrels with both Lorelai and Rory before Emily asks him to leave . Rory runs into Jess and they each betray their hurt feelings--Rory about Shane and Jess about not hearing from Rory all summer . Francie targets Paris and Rory for a world of trouble if Rory doesn't stop Paris from running the student council like a dictatorship . </Td> </Tr> <Tr> <Th> 46 </Th> <Td> </Td> <Td> "Application Anxiety" </Td> <Td> Gail Mancuso </Td> <Td> Daniel Palladino </Td> <Td> October 8, 2002 (2002 - 10 - 08) </Td> <Td> 175003 </Td> <Td> 5.2 </Td> </Tr> <Tr> <Td_colspan="8"> Rory's application for Harvard arrives, plunging Rory, Lorelai and Emily into a frenzy . A Chilton seminar on college applications only adds to Rory's anxiety and sends Paris into a tizzy . Taylor steamrollers Luke into opening a soda shop next to the diner . Lane places an ad in the paper for a band and finds a musical soul mate . Lorelai and Rory have dinner with a Harvard alumnus and his family which may assure her chances of acceptance . Dean has a talk with Rory about their future after she goes to Harvard . </Td> </Tr> <Tr> <Th> 47 </Th> <Td> </Td> <Td> "One's Got Class and the Other One Dyes" </Td> <Td> Steve Robman </Td> <Td> Daniel Palladino </Td> <Td> October 15, 2002 (2002 - 10 - 15) </Td> <Td> 175004 </Td> <Td> 5.4 </Td> </Tr> <Tr> <Td_colspan="8"> Lorelai's stint in the Stars Hollow High School local business success speakers forum gets derailed by some controversial personal questions, much to the delight of Luke and the consternation of some PTA mothers . Luke and Jess argue about the women in and out of their lives (and their closets). Lane alleviates her frustration about the strictures of her household and the future of her band through a colorful, if temporary, display of independence . Rory runs into Shane one too many times and succumbs to a severe bout of snarkiness . </Td> </Tr> <Tr> <Th> 48 </Th> <Td> 5 </Td> <Td> "Eight O'Clock at the Oasis" </Td> <Td> Joe Ann Fogle </Td> <Td> Justin Tanner </Td> <Td> October 22, 2002 (2002 - 10 - 22) </Td> <Td> 175005 </Td> <Td> 5.5 </Td> </Tr> <Tr> <Td_colspan="8"> Lorelai attends Emily's society auction where she meets a very handsome man, but neglects to get his number, forcing her to ask her mother for it . After a disastrous first date, Lorelai turns down an invitation to another, not realizing that Emily and Richard have a lot invested in her dating this son of their friends . After Lorelai and Rory agree to water their new neighbor's lawn while he's out of town, Jess comes to Rory's rescue when the lawn's sprinker system malfunctions . </Td> </Tr> <Tr> <Th> 49 </Th> <Td> 6 </Td> <Td> "Take the Deviled Eggs ..." </Td> <Td> Jamie Babbit </Td> <Td> Daniel Palladino </Td> <Td> November 5, 2002 (2002 - 11 - 05) </Td> <Td> 175006 </Td> <Td> 5.5 </Td> </Tr> <Tr> <Td_colspan="8"> Lorelai chauffeurs Rory to Sherry's baby shower in Boston and finds herself dragged into the festivities against her will . Miss Patty gets a new beau . Jess comes home with a car and Luke tries to find out where he got the money to pay for it . One of Stars Hollow's more eccentric citizens requests a permit to mount a demonstration in the town square . </Td> </Tr> <Tr> <Th> 50 </Th> <Td> 7 </Td> <Td> "They Shoot Gilmores, Don't They?" </Td> <Td> Kenny Ortega </Td> <Td> Amy Sherman - Palladino </Td> <Td> November 12, 2002 (2002 - 11 - 12) </Td> <Td> 175007 </Td> <Td> 5.7 </Td> </Tr> <Tr> <Td_colspan="8"> Lorelai is determined to win the Stars Hollow Dance Marathon and wrest the trophy from four - time champion Kirk, but has trouble getting a partner until she finally convinces Rory to help her dance her way to victory . Dean sits on the sidelines to cheer his girl on, and is soon joined by Jess and Shane, who spend their time making out while Jess keeps his eye on Rory . Lorelai breaks her heel, and Dean takes her place while Luke plays shoe repairman . On the dance floor, Dean realizes that Rory is attracted to Jess and breaks up with her . Rory tearfully runs off, followed closely by Jess, and Kirk is declared the winner once again . </Td> </Tr> <Tr> <Th> 51 </Th> <Td> 8 </Td> <Td> "Let the Games Begin" </Td> <Td> Steve Robman </Td> <Td> Amy Sherman - Palladino, Sheila R. Lawrence </Td> <Td> November 19, 2002 (2002 - 11 - 19) </Td> <Td> 175008 </Td> <Td> 5.7 </Td> </Tr> <Tr> <Td_colspan="8"> In the aftermath of the Dance Marathon, Kirk parades around Stars Hollow with the trophy until someone steals it, while Lorelai and Rory painfully inch their way towards Luke's . After Lorelai tells Luke about Rory and Jess, he breaks up their first kiss as a couple and then lays down some ground rules with Jess about dating Rory . Lorelai and Rory reluctantly agree to accept Richard's invitation to accompany him and Emily to his Whiffenpoof reunion at Yale, where he springs quite an unwelcome surprise on all three women . Back from New Haven, Lorelai and Rory head for Luke's, and Jess and Rory finally get to have those first kisses . Rory visits Dean to apologize and tell him that she misses his friendship . Late at night, Lorelai and Rory each curl up with some bedtime reading--the Yale brochure . </Td> </Tr> <Tr> <Th> 52 </Th> <Td> 9 </Td> <Td> "A Deep - Fried Korean Thanksgiving" </Td> <Td> Kenny Ortega </Td> <Td> Daniel Palladino </Td> <Td> November 26, 2002 (2002 - 11 - 26) </Td> <Td> 175009 </Td> <Td> 5.4 </Td> </Tr> <Tr> <Td_colspan="8"> It's Thanksgiving and Lorelai and Rory have dinner at four different places: the Kim's, where Lane has managed to get Dave invited and Lorelai is forced to eat tofurkey; Luke's, where Luke and Jess make it a foursome with Lorelai and Rory; Sookie's, where Jackson and his family have deep - fried the turkey, the lawn and just about everything else; and Emily and Richard's, where, to Lorelai's horror, Rory reveals that she has applied to Yale . Kirk gets a cat, with disastrous results . Dave asks Lane out, and then kisses her . Paris is afraid her difficulty finding a shelter volunteer position will impact her acceptance to Harvard . Dean faces off with Jess and lets him know that it's no more "Mr. Nice Guy" for Mr. Forester . </Td> </Tr> <Tr> <Th> 53 </Th> <Td> 10 </Td> <Td> "That'll Do, Pig" </Td> <Td> Jamie Babbit </Td> <Td> Sheila R. Lawrence </Td> <Td> January 14, 2003 (2003 - 01 - 14) </Td> <Td> 175010 </Td> <Td> 5.5 </Td> </Tr> <Tr> <Td_colspan="8"> Lorelai's grandmother arrives in Hartford unexpectedly on Richard's birthday and announces that she's moving back, throwing Emily into a tizzy until she follows Lorelai's advice on how to manage her mother - in - law . Rory declares war on Francie after she pulls a runaround on Paris with the Student Council . Paris finds herself in love after spending Christmas vacation with Jamie's family . After Rory and Dean bump into each other a few times, they decide to be friends again . Jess initially declines Rory's offer to attend the Stars Hollow High Winter Carnival, but changes his mind after they run into Dean and his sister Clara, who invites Rory to join them . Jess gets Dean alone at the carnival and lets him know that he's wise to his plans to get Rory back . </Td> </Tr> <Tr> <Th> 54 </Th> <Td> 11 </Td> <Td> "I Solemnly Swear" </Td> <Td> Carla McCloskey </Td> <Td> John Stephens </Td> <Td> January 21, 2003 (2003 - 01 - 21) </Td> <Td> 175011 </Td> <Td> 4.8 </Td> </Tr> <Tr> <Td_colspan="8"> Offers of dates ensue when Lorelai and Sookie attend a seminar on operating an inn and run into two handsome men--an old friend of Sookie's and his business partner . Lorelai unsuccessfully resists being deposed when her mother is sued by a former maid for wrongful termination . After Rory and Francie butt heads at the student council meeting, Francie proposes a truce and then immediately lies to Paris that Rory is trying to undermine her . Paris is crushed that her best friend has betrayed her and lashes out at her during their fencing class, leaving Rory ostracized by the rest of the student body . </Td> </Tr> <Tr> <Th> 55 </Th> <Td> 12 </Td> <Td> "Lorelai Out of Water" </Td> <Td> Jamie Babbit </Td> <Td> Janet Leahy </Td> <Td> January 28, 2003 (2003 - 01 - 28) </Td> <Td> 175012 </Td> <Td> 4.9 </Td> </Tr> <Tr> <Td_colspan="8"> Luke is opposed to having Taylor's attorney Nicole oversee the paperwork for the construction of the new soda shop until he meets the attractive redhead, who takes as immediate a shine to Luke as he does to her . Lane's clever scheme to get her mother's permission to attend the prom horribly backfires . Luke offers to teach Lorelai the fine art of angling after Alex invites her to go fishing . Rory and Lorelai clear out their garage for Lane's band and Lorelai gains a new admirer from the band . Lane and Rory have some heart - to - hearts about the men in their lives . Paris's ratcheting up the conflict between her and Rory when she calls for Rory's impeachment by the student council is brought to a swift end by Headmaster Charleston, who threatens to revoke the glowing letters he wrote to Harvard for each of them . </Td> </Tr> <Tr> <Th> 56 </Th> <Td> 13 </Td> <Td> "Dear Emily and Richard" </Td> <Td> Gail Mancuso </Td> <Td> Amy Sherman - Palladino </Td> <Td> February 4, 2003 (2003 - 02 - 04) </Td> <Td> 175013 </Td> <Td> 5.3 </Td> </Tr> <Tr> <Td_colspan="8"> Luke and Nicole have a successful first date . Jess and Dean trade verbal blows . Sherry goes into labor with only Lorelai and Rory for company until Chris shows up at last minute . Lorelai has flash backs about her pregnancy and Rory's birth . Lorelai introduces Emily to modern entertainment technology by getting her a DVD player and a couple movies . Richard and Emily decry Lorelai's and Rory's plans to backpack through Europe . The war between Paris and Rory continues when Paris picks a photo of the "Franklin" staff for the yearbook that has the worst possible shot of Rory . </Td> </Tr> <Tr> <Th> 57 </Th> <Td> 14 </Td> <Td> "Swan Song" </Td> <Td> Chris Long </Td> <Td> Daniel Palladino </Td> <Td> February 11, 2003 (2003 - 02 - 11) </Td> <Td> 175014 </Td> <Td> 5.1 </Td> </Tr> <Tr> <Td_colspan="8"> Emily guilts Rory into bringing Jess to a Friday night dinner which turns out to be an unqualified disaster . Lorelai, Alex, Sookie and Jackson go to New York for the weekend . Jess gets a black eye in an altercation with an opponent he is too embarrassed to reveal to anyone but Luke . Zack and Brian realize that Lane and Dave are hiding something from them, but miss the mark on the true nature of the secret . Rory and Jess have their first argument, and Luke helps patch things up . </Td> </Tr> <Tr> <Th> 58 </Th> <Td> 15 </Td> <Td> "Face - Off" </Td> <Td> Kenny Ortega </Td> <Td> John Stephens </Td> <Td> February 18, 2003 (2003 - 02 - 18) </Td> <Td> 175015 </Td> <Td> 5.3 </Td> </Tr> <Tr> <Td_colspan="8"> The Doose clan invades the Inn for their family reunion . Trix comes for a short visit and drives Emily crazy until Emily finally finds something scandalous to hold over Trix's head . Lane and Dave cook up a fake - date scheme with Young Chui to get Mrs. Kim to allow Lane to date Dave, but neither Young Chui's real girlfriend or Dave is immune to a little jealousy . The Stars Hollow High hockey team reaches the regional semifinals for the first time in 40 years and everyone not attending the monster truck rally turns out to cheer the team on and endure Kirk's hopelessly inept play - by - play . After Jess's too laid - back attitude about going out leaves Rory sitting home alone for most of the weekend, she takes Lorelai's advice and heads for the hockey game, where she discovers that Dean has a new girlfriend, Lindsay . </Td> </Tr> <Tr> <Th> 59 </Th> <Td> 16 </Td> <Td> "The Big One" </Td> <Td> Jamie Babbit </Td> <Td> Amy Sherman - Palladino </Td> <Td> February 25, 2003 (2003 - 02 - 25) </Td> <Td> 175016 </Td> <Td> 5.7 </Td> </Tr> <Tr> <Td_colspan="8"> Rory and Paris compete for the honor of speaking at Chilton's Bicentennial . Sookie and Jackson get some very good life (and diaper) changing news . Paris and Rory reconcile . Lorelai runs into Max and it's apparent that they're not quite over each other yet . Paris sleeps with Jamie and then has a meltdown on national television when she fails to get into Harvard, thinking her sleeping with Jamie is the cause . Rory's college acceptance letters finally arrive . Paris isn't sure what to think about the latest development in her relationship with Jamie . </Td> </Tr> <Tr> <Th> 60 </Th> <Td> 17 </Td> <Td> "A Tale of Poes and Fire" </Td> <Td> Chris Long </Td> <Td> Daniel Palladino </Td> <Td> April 15, 2003 (2003 - 04 - 15) </Td> <Td> 175017 </Td> <Td> 4.0 </Td> </Tr> <Tr> <Td_colspan="8"> A fire at the Independence Inn forces Lorelai to relocate its guests to her own house and those of her friends, and leaves her spending the night at Luke's, where she reveals her dream of being married to him and pregnant with their twins . Sookie invades Luke's with staff in tow to prepare breakfast for the Inn's guests and gets into a culinary groove with Luke after a rocky start . Questions arise about Jess' attendance at school when he receives the Employee of the Month award from Wal - Mart, and Luke discovers that he's working there more than full time . Lorelai and Rory start picking up on weird and somewhat unfriendly vibes coming from Nicole and Lindsay . Rory visits Paris, who's missed five days of school to take to her bed and hide from the world, and prompts her to stop watching soaps, call Jamie, tell her parents about Harvard, get a life plan, and rejoin the land of the living . After making extensive pro-con lists in an effort to decide whether to attend Harvard, Yale, or Princeton, Rory has a heart - to - heart with Lorelai and chooses Yale . </Td> </Tr> <Tr> <Th> 61 </Th> <Td> 18 </Td> <Td> "Happy Birthday, Baby" </Td> <Td> Gail Mancuso </Td> <Td> Amy Sherman - Palladino </Td> <Td> April 22, 2003 (2003 - 04 - 22) </Td> <Td> 175018 </Td> <Td> 4.6 </Td> </Tr> <Tr> <Td_colspan="8"> Emily and Richard rejoice when Rory announces her decision to attend Yale . Kirk sustains baking - related injuries when Rory secretly enlists the help of her fellow Stars Hollows citizens to bake the world's largest pizza for her mother's birthday party . Michel and Tobin compete over giving Lorelai the best present, but Richard wins the contest hands - down with a check for $75,000 that's actually the proceeds from an investment he made in Lorelai's name at her birth . Luke confronts Jess about skipping school to work at Wal - Mart, but is blown off as usual . When Lorelai decides to use the money to pay back her parents for Rory's Chilton tuition, Emily becomes furious with Richard for giving Lorelai the money, fearing that the repayment of their loan is a sign that she'll never see either Lorelai or Rory again . Luke makes a bad impression on Nicole's parents scaring them off with a rant on the horrors of parenting Jess . </Td> </Tr> <Tr> <Th> 62 </Th> <Td> 19 </Td> <Td> "Keg! Max!" </Td> <Td> Chris Long </Td> <Td> Daniel Palladino </Td> <Td> April 29, 2003 (2003 - 04 - 29) </Td> <Td> 175019 </Td> <Td> 5.3 </Td> </Tr> <Tr> <Td_colspan="8"> On their first free Friday night, Lorelai and Rory are at a loss over how to spend the evening, while Emily and Richard cavort at the party they're hosting . Lorelai is appointed Grad Night Treasurer and runs into a playing - it - cool Max at her first Chilton Booster Club meeting . Lane's band gets their first gig at a party and rocks the house, but Dave rocks Lane's world when he flips out after discovering that Young Chui is in love with her . A despondent Lane indulges in a little too much beer, and then drunkenly calls her mother and confesses all . When staff cutbacks at the Inn force Lorelai to do turn - down service, she becomes very unsettled at seeing a cozy Luke and Nicole in the room she's offered as thanks for Luke's help with repairs after the fire . Jess's inability to tell Rory that his frequent absences have caused him to flunk out of school and miss graduation and the prom prompts an argument between Jess and Rory, and then a full - blown brawl with Dean after Dean comes upon a tearful and distraught Rory . </Td> </Tr> <Tr> <Th> 63 </Th> <Td> 20 </Td> <Td> "Say Goodnight, Gracie" </Td> <Td> Jamie Babbit </Td> <Td> Janet Leahy, Amy Sherman - Palladino </Td> <Td> May 6, 2003 (2003 - 05 - 06) </Td> <Td> 175020 </Td> <Td> 4.9 </Td> </Tr> <Tr> <Td_colspan="8"> Fran Weston dies and Lorelei and Sookie try to buy the Dragonfly Inn . Rory and Jess try approaching each other, but fail to talk . Dean tells Rory that he's engaged to Lindsay . Mrs. Kim agrees to let Lane go to the prom with Dave . Luke finds out about Jess and Dean's fight at the party and gets even angrier at Jess . Jess' father comes to Stars Hollow and Luke tries to scare him out of town before he makes raising Jess even harder for Luke . </Td> </Tr> <Tr> <Th> 64 </Th> <Td> 21 </Td> <Td> "Here Comes the Son" </Td> <Td> Amy Sherman - Palladino </Td> <Td> Amy Sherman - Palladino </Td> <Td> May 13, 2003 (2003 - 05 - 13) </Td> <Td> 175021 </Td> <Td> 5.0 </Td> </Tr> <Tr> <Td_colspan="8"> <P> Jess heads out to Venice, California only to learn that his father's community is just as quirky as Stars Hollow . The rift widens between Lorelai and Emily . Luke tells Lorelai that Jess took off for good . Lorelai waits for the right moment to break the news to Rory, who is stressing over finals and graduation . </P> Note: This was to be a backdoor pilot for a spin - off called "Windward Circle", that would focus on Jess living in Venice, California and befriending a group of skateboarders . However, The WB did not pick up the series . </Td> </Tr> <Tr> <Th> 65 </Th> <Td> 22 </Td> <Td> "Those Are Strings, Pinocchio" </Td> <Td> Jamie Babbit </Td> <Td> Daniel Palladino </Td> <Td> May 20, 2003 (2003 - 05 - 20) </Td> <Td> 175022 </Td> <Td> 5.5 </Td> </Tr> <Tr> <Td_colspan="8"> Rory finally learns her mother can't afford to buy the Dragonfly Inn since financial aid for Yale didn't come through . She decides to take matters into her own hands with a quick visit to her grandparents right before graduation . Luke has second thoughts about a trip with Nicole after something Lorelai tells him . Jess makes silent contact with Rory after her graduation ceremony from Chilton . </Td> </Tr> </Table> <Tr> <Th> No . overall </Th> <Th> No. in season </Th> <Th> Title </Th> <Th> Directed by </Th> <Th> Written by </Th> <Th> Original air date </Th> <Th> Prod . code </Th> <Th> US viewers (millions) </Th> </Tr>

When do dean and rory finally break up