Homer starts to go through a midlife crisis until his old pen pal from Spain encourages him to live the YOLO ("You Only Live Once") life by doing everything he's ever wanted to do in life. Meanwhile, Springfield Elementary is caught up in a cheating scandal, and Lisa offers a solution.
Tropes of this episode:
- Book Dumb: Bart somehow finds a loophole when Lisa notices his grades. Lisa points this out to Bart, but Bart explains he didn't want to be like her.
- Bribe Backfire/Screw the Money, I Have Rules!: Principal Skinner offers a bribe to Kent Brockman if he agrees not to publish the school's cheating scandal and Kent reacts by publishing the attempted bribery as well.
- Cats Have Nine Lives: Referenced by Homer when he learns that "YOLO" stands for "You Only Live Once".
- Cheaters Never Prosper: Lisa gives Bart a choice she learns he found a loophole.
- Cut Lex Luthor a Check: When Lisa finds out that Bart knows a way around her honor code, she wonders why he doesn't use his skills for good. He explains that, if he did, he'd become something he swore he'd never be. He'd be Lisa.
- Either/Or Title: Parodied. During Homer's fall, a narrator asks if he'll survive and comes up with two titles for a sequel where the answer would be revealed in the style of Rocky and Bullwinkle.
- Kent Brockman News: Leave it to Kent to remind Skinner why hes there.
- Kid Has a Point: Lisa intervenes by creating an honor system.
- Loophole Abuse: Bart finds a way around Lisa's honor code..., it's shouldn't be a surprise since after all he is Lisa's brother, but Lisa begs to differ.
- Parental Marriage Veto: Marge says she never disobeyed her parents before marrying Homer.
- Rule of Three: Lisa hopes to convince all students to sign up for her honor system by convincing the toughest kid, the smartest kid and the nerdiest kid to sign.
- Toon Physics: The fall without a parachute being used should've killed both Bart and Homer, but they lived, allowing Bart to consider Lisa's plea.
- Mid-Life Crisis Car: Kirk buys a red convertible.
- Noodle Incident: Why was Skinner looking at a website about Japanese Girls with animal ears?
- O.O.C. Is Serious Business: Homer goes through a midlife crisis, but he cheers up.
- Shout-Out: To June Foray