With the wedding called off, Lorelai (Lauren Graham) is eager to escape the sympathies of everyone in Stars Hollow, so she and Rory (Alexis Bledel) take off on a road trip that ultimately leads to Harvard Univerisity, where Rory comes face-to-face with her dreams of college life, while Lorelai confronts the past that might have been.
Rory and Lorelai are in their Jeep continuing on their spontaneous road trip that started last episode. Lorelai is complaining about the lack of music, and Rory is worried about where they are. Rory asks Lorelai to stop driving before they hit the Atlantic Ocean, but Lorelai replies by saying not unless it's the Pacific. They stop at Hayden's Nut House to pick up some food for the drive. Once back in the car, Rory pulls out a map and starts talking about where they are headed, but Lorelai ignores her and calls Sookie. She explains that the engagement is off. Lorelai asks Sookie if she has started her wedding cake, the camera cuts to a shot of the beautifully finished cake when Sookie reassures Lorelai that she hasn't. Lorelai hangs up and chastises Rory for using a map. Rory says they are headed to Portsmouth, New Hampshire. Lorelai replies that she has a friend, Donald something-or-rather, that owns a Bed & Breakfast in that town. They decide to head there.
They step inside the B&B and encounter a lady asking them if they want to ring the bell that sits on her desk. Lorelai rings the bell and asks if Donald is there. The lady, Ladawn, says no. It turns out that she bought the place from him a year ago and renamed it the Cheshire Cat. Next, Ladawn takes them to room 3 after asking Rory if she wants to ring the bell, but not before the girls spot Sammy the cat lounging on the staircase. They enter the room and are surprised by the amount of flowers that decorate the walls; this is so not Lorelai and Rory’s style. Ladawn then asks Lorelai what business she is in, and Lorelai responds by saying, “Publishing.” Soon, Lorelai and Rory find the B&B’s guest book and make fun of the entries in it. The girls are now starving so they are walk down the stairs only to see a whole bunch of people in the living room of the Cheshire Cat. Not wanting to meet these people, let alone get interrogated by them, they go back upstairs despite their stomachs.
In their room, they sit on the bed in their pajamas trying to decide what to do. Rory says they should talk and Lorelai asks what about. Rory brings up the subject of Max which causes Lorelai to get annoyed and turn out the light. Rory turns it back on and a screaming match ensues. Finally, Rory gives up and they both lie down. Lorelai then says quietly, “I wish I did love him, you have no idea how much.” Rory gives her a kiss and they go to sleep. In the morning, Lorelai says that the flowers in the room had reproduced. What an awful thought. Rory discovers that Lorelai had written “Satanic forces are at work here” in the guest book. Rory then fixes the entry so it doesn't invoke the Dark Prince. Lorelai then checks the B&B schedule to see if they can get out without running into anyone. They go down the stairs to see Ladawn and a few other B&B'ers looking out the window watching Hummingbirds. Ladawn says they were worried about the two of them and encourages the girls to sit down and have some scones. Two B&B'ers join Lorelai and Rory at a table and one asks Lorelai about her work as a publisher. Lorelai responds that she works with children's books and names a few titles (The Horse that Wanted to Bark, etc.). The same B&B'er says that she thinks she read that to her grandson. Next, Lorelai says that she needs to make a call concerning publishing and leaves Rory to fend for herself.
Lorelai calls Sookie and asks what's going on. Sookie is at Luke's watching Kirk and Luke fight it out. Lorelai asks how the spreading of the ex-engagement news is going and Sookie says it's been going well, except for that Luke doesn't know yet. Lorelai asks Sookie to tell him and when she does, Luke responds by giving everyone in the diner free coffee. The B&B'ers are talking to Rory about their son, when they comment on not even knowing is she’s on the market. Rory responds that she's not, much to the delight of the B&B'ers who giggle about her having a boyfriend. But there is no more time to chat because Lorelai grabs Rory and it’s time to leave. Rory says Lorelai has abandonment issues and Lorelai asks where she’s hiding her map. Rory says she's not hiding a map, but Lorelai gets it out of her and looks at it, trying to figure out where they should go. Rory mentions Boston, but Lorelai says she knows where they are going. Rory of course asks where so she can chart a course, but Lorelai grabs the map and crumples it up much to Rory's dismay. Rory pouts and Lorelai says she'll buy her a new one.
Soon, Lorelai and Rory are standing outside Harvard and Lorelai says they should go inside. Rory responds that they can’t because they need a guide, but Lorelai insists that she can do the job herself. They spot a coffee stand, so Rory goes to get some while Lorelai looks at a bulletin board with roommate requests. A guy comes up behind her and comments on the amount of postings. He even asks Lorelai if they have a class together, he has been meaning to say hi to her. He quickly leaves and Lorelai tells Rory that she thinks she's going to like college. While on their own tour of the school, the two Gilmores stumble upon the library. Rory says it's the biggest she's ever seen. Lorelai surprises her by saying that it's only one of the 90 libraries; it houses 13 million books and the largest academic library in the world. Rory is disappointed, she thinks she's a failure because she hasn't read enough, but Lorelai replies that she doesn't think Rory has to read them all. They wander into a dorm and meet two girls who are kind of weirded out by Lorelai because her college jargon comes from reruns of Happy Days. They next enter another dorm room and Lorelai comments on the small size of the room. She even makes Rory sit at the desk and pretend like she's studying. Lorelai and Rory continue walking in a hallway with classrooms attached. They enter a room filled with students, but Lorelai leaves in search of a bathroom. As the door slams, a professor notices Rory and tells her to have a seat, mistaking her for someone in the class.
On the way back from the bathroom, Lorelai finds a wall of pictures full of past valedictorians. She looks longingly at 1990's, what her class would have been had she gone to college. After staring at it for a while, she hears Rory's voice coming from the classroom and walks back. Rory has now become involved in the class discussion and is talking with the professor. She looks up to find Lorelai in the doorway and once out in the hallway, she says how much she loves college! Back at the B&B, Ladawn is carrying down their bags. Lorelai comments how Sammy the cat has moved from her perch on the stairway, but Ladawn says he is never on the stairway. Lorelai debates with her about it for awhile and then gives up. With Lorelai and Rory almost done at the B&B, Ladawn says she can't wait to go up and read what they wrote in the guest book. Lorelai and Rory make it back home to Stars Hollow and spot the chuppah Luke had made in the front of their house. Rory says she had forgotten about it and Lorelai says she had too. She walks to the chuppah and tries not to cry. Next, Lorelai is conducting a slide show with pictures from their Harvard trip at Emily and Richard’s house. Emily is complaining about the quality of the slides and says next time she goes to Harvard they are going to do it properly. She then asks Lorelai what Max would think about them leaving so abruptly. Lorelai responds by saying that she should have told Emily. This causes Emily to think that Max and Lorelai have eloped. Lorelai calms her down by saying that she called off the wedding and her and Max are not together anymore. In true Emily fashion, she tells Lorelai that she’ll have to return her gift. Lorelai then continues to bug her mom about what the gift was.
Later, the girls park the car somewhere in the town and talk about if it's close enough to the curb. Lane comes running up and hugs Rory and they talk about Korea and how it wasn't so bad. The girls are glad to see each other again. Lorelai enters Luke's Diner and Luke apologizes about the wedding. He says he's sorry for being mean to Max. Lorelai says he already apologized, and it was nice of him to make the chuppah. He gets riled up and says he forgot about that, and that he'll get rid of it now, but Lorelai tells him she wants to keep it. Luke asks about their trip and Lorelai explains how Rory fit so well at Harvard. Luke wonders how that made Lorelai feel. Lorelai says she loved it and hated it. It got her thinking about her life then and life now. She then asks Luke about lines of credit at a bank and says she wants to move forward with her plans to open the inn with Sookie. She gets up to leave and Luke says to let him know when she needs help. Rory and Lane are talking about their trip when Lorelai comes up. Rory asks if she can go to Lane's for awhile and they walk away squealing about Harvard. Lorelai looks sad; she pulls out her cellphone and calls Sookie to tell her that she thinks they are ready to move forward with the “inn thing.” She smiles and gets back in the car.
- Rory – What did that sign say? It said, "Don't" or "Death" on it!
- Lorelai – Did you hear? I used 'existentialist' in a sentence
- Rory – I heard
- Lorelai – I've always wanted to do that
- Rory – It was very impressive
- Rory – (about the guest book) Wait, you weren't writing in this, were you?
- Lorelai – Maybe just a few random thoughts.
- Rory – (reading) "Satanic forces are at work here." Mom!
- Lorelai – What?
- Rory – What? We can't write that in here, that's what. Here... "Sat and forever am at work here."
- Lorelai – That doesn't make any sense.
- Rory – It doesn't involve the Dark Prince, so I think it's good.
- Rory – I've been frittering away my life!
- Lorelai – You don't fritter.
- Rory – Did I mention I suck?
- Lorelai – Yes.
- Rory – Well, I do.
- Lorelai – No.
- Sookie made Lorelai a wedding cake, that she named Clyde.
- Sookie tells Luke that the wedding is off and he buys free coffee for the whole diner.
- Lane returns from Korea.
- "Perfect Situation For A Fool" by Jai Josefs, Roy Brown
- "L-O-V-E (Bo Tuesday)" by Irving
- "Gypsies, Tramps And Thieves" by Cher
- "How To Dream" by Sam Phillips
- "Anarchy in the U.K." by the Sex Pistols
- Goodnight Spoon by Keith Richards
- Alice in Wonderland by Lewis Carroll
- Tuesdays with Morrie by Mitch Albom
- Who Moved My Cheese? by Spencer Johnson
- Henry James
- Rory – (to Lorelai) Wow, your Behind the Music is gonna be really wild.
- Lorelai – To figure out exactly what happened, you'd have to dig up Freud himself and have him work on me full time.
- Lorelai – Okay, I think we just found the first room in the history of the world that would've made Liberace say, "Whoa, step back. No one's that gay".
- Lorelai – Rory, stop it. We are not going to have this fight in a flowery bedroom with dentists singing Gypsies, Tramps and Thieves in the background. It's too David Lynch!
- Rory – (to Lorelai) You do realize that all of your college kid jargon comes from Happy Days and the Valley Girls song.
- Lorelai – I may never get married. I may be a free spirit my whole life, or fall in love with a separated Catholic guy like Katherine Hepburn did and then not get to go to his funeral when he dies.