After Rory is accepted to the prestigious Chilton Preparatory School, Lorelai is forced to go to her wealthy parents for financial assistance. Her parents happily loan their daughter the money in exchange for an end to the estrangement and a family dinner every Friday night. Unfortunately, things hit a snag when a cute new transfer student flirts with Rory, leading the younger Gilmore to wonder whether leaving Stars Hollow High is really what she wants.

When Rory announces at Friday night dinner that she has to pick a team sport to play at Chilton, Emily insists that Richard take Rory to the club and teach her golf. Although Rory tees off to a rocky start, she soon gets into the swing of things and has a great time walking and talking with Richard. Later, Lorelai's mixed feelings as Rory tells her how much she enjoyed being with Richard at the club provokes her into an intensely stupid argument with Rory, which is soon patched up when Lorelai realizes that she's not losing Rory to her parents. At the Inn, Lorelai has her hands full overseeing all the preparations for an ornate double wedding ceremony and contending with a pair of spoiled and quarrelsome twin brides, their exhausted mother, their twin grooms, Michel, and the rest of her staff.

During dinner at her mother's, Lorelai finds out that not only is there a formal dance at Chilton, but that Rory doesn't want to go. On the way home, Lorelai convinces Rory that she needs to have this experience, and even offers to make Rory a dress. Lane prods Rory into asking Dean to go, and she nervously does. Even though he says he doesn't really like dances, he agrees to go with Rory. When Emily arrives at Lorelai's the night of the dance to see Rory off and take some pictures, she finds that Lorelai has thrown her back out. She decides to stay and to take care of Lorelai,and they manage to get in some nice mother-daughter bonding during the course of the evening. The dance starts off well; Rory's dress is complimented, Dean is admired, and Paris is embarrassed when everyone finds out that her date is her cousin and that he insisted upon being paid to escort Paris. Unfortunately, Tristan baits Dean, and they almost get into a fight before Dean warns him never to come near Rory aga

Luke's ex-girlfriend Rachel arrives in Stars Hollow unexpectedly, and immediately picks up on the attraction between Luke and Lorelai, which they deny. Rachel decides to stay for awhile, which leaves Luke and Lorelai with mixed feelings. Lorelai and Rory are amazed when Emily agrees to excuse Rory from Friday night dinner so that Rory and Dean can celebrate their three month anniversary. When Lorelai arrives for dinner, she discovers the source of Emily's largesse -- her mother has invited another guest -- a man with whom she secretly hopes to fix Lorelai up. After a painful dinner with one of the world's most boring men, Lorelai attempts to escape through the window of her old bedroom, but is caught in the act by Richard. When he is forced to admit that even he is bored by the man, he uncharacteristically covers for her and lets her make her getaway. Back in Stars Hollow, Dean treats Rory to a wonderfully romantic dinner, and then gives her a present -- a car that he's restoring for h

Christopher comes to town on a business trip with his girlfriend Sherrie in tow. Since Sherrie and Christopher's relationship is getting serious, Sherrie wants to begin bonding with Rory -- on Friday night. Without consulting Emily, Lorelai excuses Rory from The Gilmore Friday Night Dinner, and takes Christopher with her instead. When Emily finds out about Sherrie over cocktails, she has a meltdown and rushes off to the kitchen. Lorelai follows her there and finds out that Emily has always envisioned that Lorelai and Christopher would end up together. Now that she sees that this isn't going to happen, Emily blames Lorelai for always keeping him, and everyone else, at arms length. After mulling over her mother's words, the next morning Lorelai tells Christopher that she's always thought that they would get back together, too, and that's why she's never had a relationship that lasted, including the one with Max. Christopher gets very angry, refusing to accept the responsibility for the w