In this episode Headmaster Charleston calls to ask Rory to lead around a prospective Yale student for a few days, Miss Patty celebrates her 40yrs in show biz, and Lorelai finds out a dark secret of Luke's.
With Rory, she agrees to take on the prospective Yale student, Anna, and Paris is seeking in house help from her counselor. When Anna arrives she seems to be as sweet as can be and excited about college life, but it seems disappointing to Rory to see that she is more excited about parties and no uniforms rather than the prestigious acadamia of Yale. As Rory is showing Anna around campus she runs into Logan in the library. He catches them sniffing a very old book "Did I just catch you smelling that book Ace?" Rory: "Yes, Anna this is Logan, Logan this is Anna, a prospective Yale student from Chilton. What are you doing in a library?" Logan: "You have to take Anna to the pub it is where everyone hangs out, shh don't tell anyone I was here." and walks away, leaving Rory with the excited Anna who is dying to go to the pub. After caving she takes Anna to the pub where she runs into Marty, after leaving her alone for like two seconds, she finds Anna being entertained by some boys looking for a good time, trying to get her to come to a keg party. Rory shews them away and warns Anna that the boy's intentions were anything but honorable. When they get back to the dorm, Rory has realized that Anna has had one too many coffees and will be up for hours, but lets her watch tv on the couch until she falls asleep. The next day Rory takes Anna to her Philosophy class and tries to keep her awake. During the class Logan and Collin bust in with a stunt/skit about Rory stealing their balls and hearts of these two men and that she needed to choose one. Completely embarassed, Rory tries to ignore them, then Fin jumps in clothed in a police uniform and says a few remarks and escorts them out, then they all come back for a bow, then leave. Rory's face turns beat red and is very annoyed by the show, but Anna is delighted. In the cafeteria Logan comes and sits with Rory and Anna only to find that he has upset Rory. Rory tells Anna to make her way to the Fro-yo social and that she would meet her there so that she could talk to Logan alone. When Logan begins to ask her why she is so upset the discussion leads to her calling him a few degrading names and my personal favorite "butt-face miscreant", which Logan replies "butt-face miscreant?" and tries to convince Rory that what he did was all in good fun. When Rory leaves to go to the Fro-yo social she does not find Anna and begins to panic. She recuits Marty to help find her, during their search, Headmaster Charelston calls and informs her that Anna was picked up by the police from an out-of-hand party. On their way back Rory begins to tell Marty about what Logan did and how annoyed she was also wondering what she did to deserve it. Marty then jumps in and asks Rory if she could really be that naive and pointed out that this was Logan's way of telling her that he liked her. Back with Paris, her counselor encourages her to begin speed dating where she hooks up with Doyle. They decide to cut to the chase and sleep together that night, which Rory finds out about when she finds Doyle in Paris' robe at the dorm.
With Lorelai, she has been invited to Miss Patty's celebration of 40 years in show and tries to get Luke to join her only to find that this is on Luke's dark day. After following him around town she runs into Luke argueing with an old lady over his father's boat. The woman was moving and needed to get it moved asap. After much frustration Luke tells her to trash the boat and leaves. After Lorelai decides to buy the boat and store it in her garage thinking that one day Luke may wish that he still had it. Later on when Luke comes over to talk to Lorelai about what was going on with him that day he discovers the boat and gets mad at Lorelai for not listening to him and his wants. Lorelai ends up attending the party with Sookie, later on Luke apologizes for blowing up at her and reveals that he is now glad that she saved the boat. The reason for Luke's dark day is because it was on this day that his father died.
Lastly, Rory asks Richard for a favor in getting back at Logan. Richard joins Rory at Yale where he walks up to Logan unannounced and begins to talk to Logan about how he and his parents are excited about his and Rory's union and awaiting a wedding, obviously freaking Logan out. Both Rory and Richard have fun with this little prank and this is the end of the episode.