Lisa is put on anti-depressants after reading Internet reports that Springfield will be a barren wasteland in 50 years. Meanwhile, Bart and Milhouse's friendship is, once again, strained, thanks to a girl named Jenny (voiced by Anne Hathaway).
Tropes:
- Bait-and-Switch: At the end, Bart is seen offering someone flowers and asking for forgiveness. He was talking to Milhouse.
- Book Ends: Bart and Milhouse play a huge prank on the school at both the beginning and the end of the episode.
- Black Comedy Animal Cruelty: Via subtitled squeaks, we learn from a dolphin that Bart once filled its tank with 7-Up.
- Does This Remind You of Anything?: Nelson gives Bart romantic advice, which amounts to being a Loving Bully, and gives him a piece of gum to put in the girl's hair before handing him a second one "in case you get lucky."
- Driven to Suicide: One of the Internet reports on what Springfield will be in 50 years mentions the last polar bear hanging itself in prison.
- Exact Words: Attempting to impress Jenny and desperately fishing for a good deed he's done, Bart tells her he spends a lot of time with a "mentally-challenged man," pointing out Homer. Although she's later nonplussed to discover that Homer is Bart's father, it doesn't hurt their relationship as it's not exactly a lie.
- Friend Versus Lover: Milhouse resents Bart's relationship with Jenny, as Bart promised to visit him while he was grounded for being suspended (for a prank Bart masterminded) before blowing him off to pursue Jenny.
- Gigantic Gulp: Bart drowns his sorrows with a 512-ounce Squishee (that's 32 lbs, or 14 kg).
- Hope Spot: After Bart reveals to Jenny about the lies, it looks like she is going to forgive Bart as she smiles...only to frown and dump Bart.
- Humiliation Conga: In additional to being exposed as the "Ay, Carumba" kid by Milhouse before Jenny, Bart is seen crying back home after she dumps him.
- Idiot Ball: Skinner and Chalmers were right to suspend Milhouse for his role in sabotaging the school and refusal to tell who was helping him. What doesn't compute, however, was their inability to realize that it was Bart. You don't have to be a longtime Simpsons fan to know that Bart and Milhouse are always together getting into some kind of mischief, combined with Bart's bad boy reputation, they should have known who the other culprit was. In fact, when Bart and Milhouse pull another school prank at the end of the episode, Skinner immediately knows Bart was behind this one, which further begs the question of why he didn't piece it together the first time.
- Leaning on the Fourth Wall: Lisa acknowledges the Two Lines, No Waiting structure of the episode at the climax.Lisa: Bart, in my concurrent adventure I learned a really important lesson.
- Literal Metaphor: Milhouse warns Bart that he might not be able to "hold his tongue" next time he sees Bart and Jenny together. Then walks off holding onto his tongue, commenting that it's hard to do.
- Loving Bully: Nelson's advice with regard to Jenny is to punch her and stick gum in her hair. He later similarly advises Bart to punch Milhouse as they're making up.
- Made Myself Sad: After Bart gets dumped, Homer attempts to reassure him by telling him he'll always have his family—causing him to start crying louder. Homer joins in with "I know!"
- Mushroom Samba: Lisa starts seeing smiley faces everywhere once she's on the pills. It reaches the point where Marge catches Lisa almost ready to make out with an electric fan.
- Picnic Episode: Bart takes a Retirement Castle volunteer out on a picnic, where they eat Bart's PB&J sandwiches (his secret recipe: "No PB, Double J"). During said picnic, they attempt to ignore Homer being "mugged" by his own reflection in the pond water.
- Positive Friend Influence: Deconstructed with Jenny. Bart gives up his life of pranks and mischief for her sake, but him praising her for her influence into becoming a better person in his confession wasn't enough to save their relationship, and after she dumps him, he goes back to pranking people.
- Pseudo-Romantic Friendship: Bart buys roses for Milhouse to apologize for his shoddy treatment and they pull a makeup prank together.Nelson: Punch him!
- Take That!: To Shrek the Third. Apu promotes a Shrek Squishee contest, where if you answer the trivia correctly, you get a 10% discount off any Shrek DVD, except the first two films.
- Tempting Fate: Milhouse rings the Simpsons' doorbell right after Jenny says nothing will change the good opinion she has about Bart.
- Third-Person Person: Shauna refers to herself in third person before explaining that she's Shauna.
- Toxic Friend Influence: Incredibly, Homer thinks Milhouse is this for Bart.Homer: Well, I'm glad they suspended Milhouse. He's a bad influence on you. (Homer sees El Barto graffiti, including an obvious Bart self-portrait) You know, I think Milhouse is El Barto...Hmmm.
- We Used to Be Friends: Milhouse and Bart have a heated discussion on this subject, with Bart invoking John Adams and Thomas Jefferson as an example of friends who just happen to stop talking to each other for a long time.Milhouse: Just because you saw one episode of one miniseries doesn't mean you get to use it as a whip!
- You Are Grounded!: This happens to Milhouse at the beginning of the episode, after taking the blame for Bart's prank, thus marking the first time since Season 15 that it had been used, and the first of four references to it across Seasons 20 and 21.
