In the kitchen at the Dragonfly, Lorelai and Sookie are deliberating on how to bring more businessmen to the Dragonfly. The best scheme they can come up with is to have booze, Bill Mahr and whores as their special draw. They decide that perhaps they shouldn't make such a serious decision when they are feeling so silly. Jackson enters the kitchen uncharacteristically dressed in a suit but carrying the usual box of vegetables. Lorelai asks Jackson how he thinks that they can lure the businessmen to the Dragonfly but the town selectman duties are beginning to overwhelm him and he responds in a rather hostile fashion. In a blatant attempt at subterfuge, Lorelai hands Jackson a sheet to sign while mumbling something about ordering vegetables. Unfortunately Jackson decides to read the paper and notices that it is request for the two extra parking spaces for the Inn. Annoyed with the attempted deception, he takes his leave. Sookie appears immediately and offers to forge his signature.
At the Yale cafeteria, Rory is eating lunch with Richard who is chatting about his work, his travel and the books he has read of late. He suddenly realizes that he has been talking a lot and apologizes; he expresses the hope that he has not become tiresome to Rory. Rory dismisses his concern, assuring him that she enjoys his company. She soon realizes that since the separation Richard seems to have considerable free time and seems quite lonely.
Lorelai drops in to the diner for coffee. As she pulls out her wallet to pay, Luke tells her to forget it but Lorelai insists. She explains that this is his business and she should pay. They have a debate about her tipping practices and confirm their date for the next day. As Lorelai leaves the diner she bumps into Dean. They chat awkwardly for a moment and say good-bye.
Lorelai and Rory arrive for Friday night dinner to find Emily has purchased a panic room. Emily feels that she is a woman living alone and may need protection. Lorelai and Rory remind her that Richard just lives in the pool house but she is unconvinced that he would bother helping her if she was in jeopardy. Emily begins to make the drinks and to her utter annoyance she finds there is nothing on the bar cart with which to make the drinks. After the maid searches but doesn't find any gin, Emily drags the girls into the pool house to get them the drinks they want. While in there, Emily makes it her mission to find out what Richard has been up to. She is upset to find it smell of cigars and newspapers strewn about. She finds what she believes are signs of his debauchery…a bowl full of mints and a sequined vest. Rory is very uncomfortable snooping in her grandfather's place and begs Emily to leave. Finally, they grab the gin and exit.
A little later in Luke's diner, Lorelai and Rory are discussing Emily's bizarre behaviour. Along with their ice cream and pie, Luke brings a grapefruit trying to get them to eat healthier. Once again the topic of tipping comes up. Rory already knew that it wasn't necessary to tip the proprietor and when asked why they had been doing it all these years she replies it was because they liked him. Rory tells Lorelai that Dean has moved in with Kyle and she's going over to see him. Lorelai suggests she invite him to join them for ice cream but Rory is concerned about the awkwardness between her and Dean. Lorelai tries to convince her that there is no awkwardness on her part and suggests that they should double date. Luke comes by the table and hears Lorelai suggest they all do something together. Luke readily agrees, not realizing that 'all' includes Dean. He didn't know that Rory and Dean were dating again. He is less than enthused by the prospect of including Dean but agrees to go.
At Lane's apartment, Brian is teaching Zach a new song. Zach is struggling to learn the song so they decide to take a break. Since Lane declared her feelings to Zach, he has yet to say anything to her. She tries to get him to open up by asking him how he is but he tells her about his dentist appointment and the nasty state of his gums.
Rory drops in on Dean at Kyle's apartment for a quick visit. Her phone rings and it is Lane bemoaning the fact that Zach did not react at all when she told him she liked him. Dean is making romantic overtures towards Rory making it hard for her to concentrate so Lane tells her she will call again when she isn't so distracted. Rory broaches the subject of their date the next night. She explains Lorelai's idea of a double date with her and Luke. Although Dean is concerned about the weird factor, he agrees to go.
The next day Rory and Lorelai are on the phone finalizing arrangements for their double date when another call comes in. Lorelai puts Rory on hold while she answers a call from Emily. Emily is calling with the code to open the panic room. Lorelai recommends that she give the code to someone who lives closer, like Richard for example but Emily has no confidence that Richard would come to her aid if she were in trouble. Lorelai takes the code and goes back to her call with Rory. She tells her about Emily's call and Rory expresses concern about her grandparents marital situation. She tells Lorelai about her lunch with Richard and how much he seems to miss Emily. Neither Lorelai nor Rory know what to do to help them. They hang up the phone and Lorelai sits pensively on her couch.
A little later, Lorelai knocks on the door of the pool house. She sits down and through a little prodding finds out that the reason the papers are strewn about is because his butler is away due to a family emergency, the bowl of mints is just random collection and the sequined vest exists because Richard has joined a barbershop quartet. Lorelai encourages Richard to tell Emily what is going on in his life. Richard doubts that she would be interested to know but Lorelai explains they have been married for forty years and she is interested in his life as he would be interested in hers.
The next morning at Lane's apartment, Zach is shaving at the kitchen sink while Lane washes up beside him. Zach still has not acknowledged Lane's admission that she likes him as more than a friend. She finally forces the issue by telling him that she has changed her mind, that she was mistaken and that she really doesn't like him in that way. Zach looks nonplussed as she walks away.
That night Luke and Lorelai are walking arm in arm on their way to meet Dean and Rory. Luke seems less than enthused about the date and complains when he sees Dean wearing dress slacks. After a self-conscious greeting, they discuss getting some take-out and going to the "Black, White and Read" theater for the movie Cool Hand Luke. When they enter the theater, a sleepy Kirk jumps up and admits them to the movie. They sit on 'Big Red' and begin eating their food. Kirk informs them that the first twenty minutes of Cool Hand Luke was destroyed in a small fire. Lorelai and Rory decide with enthusiasm that they will watch The Adventures of Pippi Longstocking instead. Although Dean has seen the movie several times with the Gilmore girls, Luke asks if it is a kid's movie. They are amazed to hear that Luke is a "Pipi" virgin. The movie begins and Lorelai and Rory sing along with the introductory song. As the movie continues, Luke stares over at Rory and Dean cuddling. It seems to bother him and when he asks Dean for the popcorn he snaps at him. Lorelai sends Rory and Dean off to get more popcorn then questions Luke about his attitude. He complains that he wasn't sharing the popcorn but he soon admits what the real problem is…
Luke: Does he have to be all over her like that?
Lorelai: Who? Kirk? It's healthy for him. His complexion has never been better.
Lorelai: All they were doing was holding hands.
Luke: (Sarcastically) Yeah. It was that innocent.
Lorelai: Unless he has a third hand, he wasn't holding anything he wasn't supposed to be holding.
Luke: And the way he grabbed that drink from her and started slurping on it.
Lorelai: She gave it to him to drink. Come on, chill. For me. And for Rory. It's important.
Luke: I said I will, and I will.
They all get back to the movie but Luke continues to watch Dean with disapproval.
At the diner, Lane is cleaning the counters when Zach comes in. As he shifts from foot to foot uncomfortably, he tells Lane he has something to tell her. Lane turns her full attention to him and he begins by explaining that she knows him and she knows it takes him a while to process things. He suggests to her that he wasn't about to sweep her off her feet and he hopes that's not what she expects. She assures him it's not and asks him if he wants something to eat. As he decides what he wants, Lane smiles knowingly.
At Lorelai's house after the movie, Lorelai offers beverages to her guests. The friction between Luke and Dean continues until Lorelai pulls out the Bop-It, the game she uses when a gathering is in dire trouble. Unfortunately the conflict between Luke and Dean escalates as the competition of the game brings out the need to win. Finally Dean decides it's time to leave. Rory expresses her frustration that if 'people' weren't into the evening they didn't have to come. Luke attempts to blame the problem on Dean but Rory is not hearing it. She leaves for Yale. Luke begins to regret his behaviour. He resents that Dean has broken her heart before and that he married Lindsay even though he was pining over Rory. He doesn't think that Rory can trust that he knows what he wants. He explains that he doesn't feel Dean is good enough for Rory…
Lorelai: Well, who is? Jess?
Luke: No, not Jess. A prince, maybe. One that's in line to be king. Not one of those waiting-for-a-brother-to-die ones, but a real one. If not a prince, someone who's gonna be good for her. You know, Rory is like Pippi.
Luke: She can have adventures and be free, she's smart. The whole world's waiting for her.
Lorelai: (Incredulous) You're comparing Rory to Pippi Longstocking?
Luke: (Counting on his fingers) Pippi is strong and independent. She can lift a horse above her head. Uh-huh. And beat up bullies and build a hot-air balloon. She's unique, like Rory. But I guarantee you, if Pippi had met Dean, there would be no horse, no balloons. He'd drag her down to his level, spend all her gold coins, and poof, like that, all her dreams would be gone.
Lorelai: It's Rory's choice who she chooses to be with. Not yours, not mine.
Luke: Does it feel right to you? Are you okay with this Rory-and-Dean thing?
Lorelai: (With a sigh) I just need this to work.
Luke: Look at me. Not stopping till he's upset every person that means anything in the world to him in one night. (He hugs her tightly.) You want a beer?
Lorelai: Yes. (They sit on the sofa with their beer and she suggests pensively) Maybe if I brought out the Twister.
Richard enters the main house to find Emily writing correspondence. He has taken to heart Lorelai's suggestion to let Emily know what he is up to and begins to tell her about his barbershop quartet. Emily seems pleased with this information. When Richard stops to look at the panic room, Emily explains and he accepts this information without question.
As Rory leaves for Yale, she sees Dean in the street and stops to talk to him. She apologizes to him for the nasty end to the evening and they speak wistfully of the past. They kiss good-bye and leave for their respective apartments.