Bart discovers that Cletus the Slack-Jawed Yokel's daughter, Mary, is the only girl who ever liked him, and the Simpsons head to New York [[RunningGag (again)]] so Bart can be with her after finding out that Mary has been hired as a ''Series/SaturdayNightLive'' writer.
* AbsenteeActor: Greta Wolfcastle and Shauna Chalmers are the only ones of Bart's girlfriends so far that we don't see in this episode.
* AlmostKiss: Happens between Bart and Mary.
* BaitAndSwitchComment: Bart tells Homer that New York is better now because his two least favorite buildings have been destroyed, setting up for a very tasteless joke about the September 11th attacks on the Twin Towers of the World Trade Center (since the last time Homer was in New York City, he had to wait at the towers because his car was parked there), but Homer really meant Penn Station and Shea Stadium. ("Lousy outdated relics!")
** To most of Bart's love interests. They even got their original voice actresses.
** Also to the last time the Simpsons visited New York City.
** The store "Neat & Tidy - Piano Movers" from ''[[Recap/TheSimpsonsS7E17HomerTheSmithers Homer the Smithers]]'' is briefly seen during the race at the beginning of the episode.
* TheCameo: Sideshow Bob briefly tries to kill Bart before a train hits him.
* CuckoldHorns: A vendor hands them out at a Shakespeare in the Park performance. One guy buys a pair, then finds his date kissing the man next to her. "It works!"
* RagsToRiches: The crab juice vendor hit it real big and now has a huge company building solely on selling said crab juice.
* ShesAllGrownUp: Mary.
* VillainDecay: Sideshow Bob sneaks behind Bart and, before having a chance to kill him, is hit by a train and taken away. Bart doesn't even acknowledge Bob's presence.