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 (again) so Bart can be with her after finding out that Mary has been hired as a Saturday Night Live writer.
Tropes:
- Almost Kiss: Happens between Bart and Mary.
- Awful Wedded Life:Homer: You've learned a very valuable life lesson, boy, which is that love doesn't exist, except briefly between a man and a woman before marriage. After that, it's just hanging out with someone who kind of hates you, but you can't get it together to leave.
- Bait-and-Switch: Homer tries to convince Bart not to go to New York on account to what happened the last time they were there. Cue a flashback of Homer and Marge...in a parody of Sweet Smell of Success.
- Bait-and-Switch Comment:
- Bart tells Homer that New York is better now because his two least favorite buildings have been obliterated, 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 ("Lousy outdated relics!")
- Mary's parting words to Bart:Mary: Bart, if any girl tries to fix you, let 'em, because you got a couple of big problems. But mostly, you're great!
- Borrowed Catchphrase: When Bart visits Jenny from "The Good, the Sad and the Drugly," she shuts him down with an "Eat my shorts!"
- Call-Back:
- 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 Homer the Smithers is briefly seen during the race at the beginning of the episode.
- Call-Forward: Bart teases Lisa for attending a party with Milhouse as her date and predicts a kid who will look exactly like Milhouse, while Lisa insists "We're not having a baby!" and retorts that at least she has a date, unlike Bart, whose girlfriends are always temporary. This perfectly predicts their adult lives as seen in the previous season's Flash Forward episode "Holidays of Future Passed": Lisa is married to the ever-loyal Milhouse but is a Truly Single Parent to their child (genetically engineered from the best DNA of each of them, therefore none of his), while Bart's unhappily divorced and single.
- The Cameo: Sideshow Bob briefly tries to kill Bart before a train hits him.
- Comic-Book Time: Kidanova or not, good luck going through all these girlfriends after turning nine and before turning eleven.
- Continuity Cavalcade: In a montage, Bart visits Jenny from "The Good, the Sad and the Drugly," Darcy from "Little Big Girl," Gina from "The Wandering Juvy," and Nikki from "Stealing First Base." We also see that he keeps a photo of himself with Jessica Lovejoy from "Bart's Girlfriend."
- Couch Gag: One dedicated to Maggie Simpson in "The Longest Daycare", which was released just before this episode aired.
- Cuckold Horns: 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!"
- Exact Words: Mary consoles Bart upon leaving him by saying there will be "other Mary Spucklers"—for instance, her two sisters who are also named Mary.
- Girl of the Week: Lampshaded by Lisa, who specifically mentions that "about a week" is as long as Bart can get a girl to stay with him. This causes Bart to doubt his ability to get a girl to really care about him.
- Kidanova: The episode acknowledges the many, many girls Bart has dated throughout the show (the Continuity Cavalcade of references doesn't even cover all of the ones we've seen and shows a few we haven't seen).
- Made of Iron: If subsequent episodes are any evidence, Sideshow Bob survived being hit by a train head-on.
- Parental Favoritism: Bart attributes Mary's prettiness in comparison to her siblings to the fact that she was given milk to drink as a kid instead of white paint.
- Rags to Riches: The khlav kalash vendor hit it real big and now has a huge company building solely on selling said khlav kalash and crab juice.
- Took a Level in Jerkass: Darcy and Gina, who ended their relationships with Bart on good terms, were not happy to see him in the least for some reason. Nikki on the other hand still flip-flops on the matter.
- Villain Decay: 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.
- A Wild Rapper Appears!: Parodied; when Mary's about to perform a country song she wrote for Bart, Bart offers to "do a rap in the middle of it" and she politely suggests he just listen. He tries to add one anyway.Mary: A boy I knew turned up again / Kinda liked him way back when / Chased him 'round the livestock pen...Bart: Rollin' on my skateboard, pimpin' like a drug lord— (she shushes him)
