Rory, under obligation to her Grandmother, formally comes out to society. Lorelai gets a second surprise when Christopher agrees to fulfill his fatherly deb duties. Richard, growing increasingly hostile, vents his frustrations about being "phased out" of his job. A third surprise hits when Christopher tells Lorelai about Sherry, his new girlfriend.
Rory and Lorelai are greeted by yet another new maid at Emily and Richard's house. The two of them are here for their weekly Friday night dinner. As they walk inside, the girls hear Emily and Richard bickering at each other about how Richard isn't allowing Emily to attend her parties of the Starlight Foundation. Richard is also complaining about how busy he has been at work. Rory and Lorelai sit at Luke's diner. Lorelai reads Rory's homework and tells her it's great. Rory thinks that Lorelai's just saying that because she's her mom, but Lorelai assures her that it really is really really great. Jess comes downstairs wearing a Metallica shirt. Luke orders him to go back upstairs and change, because the Metallica shirt is not proper work attire. Jess goes back upstairs. Lorelai and Rory agree that it was a gross shirt, but a good band. During the next week, Emily is having afternoon tea with the ladies from the DAR. They are all talking about the past social events that Emily has missed. She is feeling very left out because so many things have happened that she didn't get to see. Rory comes by to pick up a book that Richard left for her, and all of Emily's friends comment on how much Rory looks like Lorelai. Rory leaves to get the book and the ladies ask Emily if Rory will be presented at the Debutante Ball. Emily said no, but all of her DAR friends persuade her to ask Rory if she would "come out".
Rory comes home and tells Lorelai that she is "coming out". Lorelai is first surprised because why in the world would Rory want to be a debutante? Then suddenly her sharp Gilmore brain kicks in, and she realizes that Emily sneakily implanted this idea into Rory's brain, making her think that this is what every girl dreams of. She starts to pick up the phone to call her mother and get Rory out of this mess, but fortunately Rory stops her and says that it made Emily so happy when Rory told her she would do it. Besides it's one night, how hard could it be? It may even be fun! Lorelai and Rory start talking about everything they need for the ball, when Rory reads that her father is expected to present her at the ceremony. Rory tries not to make a big deal about it, but you can see that she is nervous when she states that she would get Taylor, or even the cable guy to do it. Lorelai picks up the phone and calls Christopher. Chris says that he'll definitely be there, and when Rory hears the news, she becomes so excited because "definitely" means that there is a 50/50 chance of him being there. Rory, Dean and Lane are watching TV while Lorelai walks around in the background, talking on the phone to Emily about the ball. Lane and Rory are telling Dean that he has to wear a tux, with tails and gloves, when Rory comes out. The thought of wearing a tux makes Dean a little queasy, but Rory points out that Neil Young looks great in a tux, and that she'll be watching BattleBots for a month to make up for this.
A horn honks outside, meaning that Christopher is here. Lorelai and Rory goes out to meet him. Rory is thrilled to see her dad (and the dictionary he brought for her), and Lorelai is surprised and somewhat pleased to see that he's now driving a Volvo instead of a motorcycle. She's even more surprised when she hears that he has a steady job, and is especially pleased when she learns what an awesome sound system he got in exchange for the passenger air bag. Lorelai is at her mother's house and the two of them are bickering over why Emily bought Rory twelve pairs of pantyhose. Richard walks in and it's apparent that something is bothering him. After he leaves, Lorelai asks Emily what's going on. Emily firmly tells Lorelai that nothing is wrong. Rory and Dean are at Miss Patty's learning how to ballroom dance. Neither is doing well. Lorelai and Christopher come in with coffee and show off their own graceful ballroom dancing skills. Lorelai and Christopher leave and go walking around with their coffee. Christopher tells Lorelai about his job, which he really likes although Lorelai thinks it sounds boring. He admits that he's always been a little jealous of Lorelai, because she figured out what she wanted at age sixteen, and it took him ten years and several failed business ventures. Rory, Dean, Christopher, and Lorelai are at Lorelai's house getting ready for the ball. Christopher is teaching Dean how to tie a bowtie while Lorelai demonstrates perfect posture by walking around with a book on her head. When Rory gets up to go get the last eggroll, Lorelai tells her that ladies never go get their own eggrolls, or anything for that matter. Dean leaves, but not before Rory remembers to give him his gloves. Rory then goes to bed too.
Lorelai and Christopher stays up talking. Lorelai is worried because Emily hasn't called at all this evening, and for the last five days she's called every five minutes. She's also worried because Emily and Richard have been openly fighting, and that's something they've never done before. Plus, Richard doesn't even want to go see his perfect angel granddaughter come out at the debutante ball. Christopher tells her that she should talk to them, and then Lorelai goes to bed. The next afternoon, Lorelai and Rory arrive at the ballroom. Rory leaves Lorelai and goes to the preparation room. She meets a girl named Libby who is totally serious about the whole debutante ball. Rory is slightly amused and tries to joke about it, but Libby tells her that she shouldn't joke about things like these, because the two minutes you're standing on the stairs this night will determine your social standing for the rest of your life. Lorelai is down at the bar when Emily arrives. Lorelai is surprised that Emily didn't get there before them. Emily is in a bad mood and starts criticizing everything; the flowers, the tablecloths, the chairs. Back in the preparation room, Libby offers a flask to Rory, who's sitting reading a book. Turns out this is Libby's fifth coming out this year. Libby asks Rory if she's going to marry her escort. Rory hurriedly changes the subject.
Downstairs, Lorelai is talking to some other mothers. Like Rory, she's totally out of her element with these people. Christopher sees her predicament and comes to rescue her, saying that he's having problems with his cummerbund. Emily walks up to them and asks if they've seen Richard. Lorelai is surprised that they didn't come together. Christopher sees that Richard has just arrived, and Emily goes over to him. They start fighting again. Rory is waiting in line in the staging area. Dean walks up to her and tells her that she looks like a really cute cotton ball. Libby walks by and says that Rory and Dean and totally getting married. Dean is confused, and Rory quickly changes the subject. She sees Christopher walk up, and Dean leaves. Rory asks Christopher to not let her fall. Downstairs, the ball is beginning. Lorelai is sitting at a table while Richard stands at the bar. Emily is trying to convince him to come sit down. He's acting childish and talking in a loud voice, which is embarrassing Emily. After he says, "To hell with society! Yes, I'm talking about you!" to the people around him, Lorelai leads her parents into another room.
Richard and Emily begin bickering again. Emily tells Richard that he has a social responsibility, and Richard asks her if she knows what he's going through at work, and tells her that she doesn't listen to him. He tries to bring Lorelai in to support him, but she stays out of it. Richard tells Emily that he's being phased out of the company, which will eventually lead to the day when they ask him to leave. Emily doesn't see that this is such a big deal and says that there are other options, but Richard tells her that he doesn't want other options; he wants to get up each morning and go to work, just like he has every morning for the past thirty years. Rory pokes her head into the room and tells them that she's next. They go back into the ballroom. Rory is announced. She and Christopher walk down the stairs. Dean is waiting at the bottom. Christopher kisses Rory's hand, Rory curtsies, Christopher walks away, and Dean walks Rory down the aisle. Emily tells Lorelai that should have been her up there, and nothing has turned out the way it's supposed to. She walks away. Later that night, in Stars Hollow, Rory, Dean, Lorelai, and Christopher are walking down the sidewalk. Rory tells Christopher that he's considered a "hot dad" among the other debutantes, and it's too bad he's not her stepfather because then she could steal him away from Lorelai. Lorelai says that she needs a burger and Rory agrees. Dean, however, just wants to get out of his tux, so he goes home. Christopher says that he's leaving early the next morning, so he has to pass on the fries but he'll have coffee with Rory the next morning. Rory goes on ahead to order their food, leaving Lorelai and Christopher alone.
Lorelai tells Christopher that it was amazing how he really came through for Rory. She also mentions that Boston isn't too far away, and that he could drop by sometimes. She points out that the traffic on the interstate can get bad on the weekends, so if he wanted to stay a little longer … Christopher says that he can't, he has to get back to work -- and to someone. Lorelai is taken aback, maybe even a little upset, but she acts happy. Her name is Sherri and she's from Boston, which is why Christopher moved there. Turns out they're living together, and Sherri made it clear that he would lose her if he didn't start getting things together. Hence the job and the Volvo. Lorelai is hurt that Christopher wouldn't change for her, but he did for Sherry. Lorelai goes into Luke's, where she finds Rory biting into her burger. They both say that they're happy for Christopher. Rory feels bad for Grandma, because the night she was so excited about totally backfired on her. Lorelai and Rory look over and see Jess wiping down the counter, dressed as Luke, complete with flannel shirt and backwards baseball cap. Lorelai and Rory are amused, but Luke is not. He tells Jess to go upstairs and change. Lorelai tells Rory that she's really lucky to have someone to talk to when things are sucking, and it must be lonely not to have that. She's thinking about Emily. The next day, Emily is gardening on the back patio when Lorelai walks in. Supposedly she had some time before her business class and came over to hang out. She tells Emily that if there's ever anything she wants to talk about with Lorelai, she can. Emily goes back to her gardening, but inside is pleased that Lorelai made this effort to talk with her.
- That should have been you up there. Nothing's turning out the way it's supposed to
- – Emily to Lorelai
- Samantha Shelton ("Libby Doty") returns to Gilmore Girls in Season 6 as Walker in "Bridesmaids Revisited."
- "The Way You Look Tonight" by Frank Sinatra
- "Thank Heaven For Little Girls" by Maurice Chevalier
- "Jubilee" by Grant Lee Buffalo
- "Du Hast" by Rammstein
- Lion King
- This Is Spinal Tap
- Moment by Moment
- Dirty Dancing
- This is Spinal Tap
- Endless Love
- The Sound of Music
- Lorelai – I think George and Martha are joining us for dinner.
- Lorelai – We didn't know we were walking in on The Lion King without the puppet heads.
- Lorelai – Does Terrence McNally know about you too?
- Lorelai – I'm still convinced she had something to do with Lily Tomlin doing that movie with John Travolta
- Christopher – Well, did you tell her about Barbara Hutton, Doris Duke, Gloria Vanderbilt?
- Lorelai – Yes, and she's perfectly willing to marry Cary Grant, get offed by her crazy butler and start designing blue jeans as soon as the ball ends.
- Lorelai – George Lucas wishes he had this sound system.
- Lorelai – Nobody puts baby in the corner
- Rory – Remember that I'll be watching BattleBots with you for a month.
- Rory – Could be a real Cirque du Soleil kind of night.
- Lorelai – Neil Young has got nothing on you.
- Lorelai – Oh Shecky, you kill me.