The episode begins with Bart and Milhouse who are having playdate. As soon as they finish the meccano roller coaster, Bart is about to send the cart down, when Milhouse suddenly realizes it is Bart who always goes first. As a fight begins between the two, they end breaking their toy, causing them both to cry. Homer and Marge then text Kirk to pick up his son. However, when Kirk arrives, they see unrecognizable changes in his appearance. He has a brand new car, a skateboard, he's lost weight, and even started to take DJ lessons. Marge questions is he is having a mid life crisis because his license plate on his car reads, "YOLO" or "You Only Live Once". Marge is glad that Homer is happy with his life, due to the fact that he has had the same job, house, and car for 20 years. Homer begins thinking that he has actually wasted his life all this time, which leads him into a deep depression.
Meanwhile, Kent Brockman and his crew visit Springfield Elementary to reveal repeated cheating by students, much to Principal Skinner's dismay. Seymour claims the only cheating going on in this school is on Dewey Largo's diet; however Kent shows 30 identical "What I Did This Summer" reports. Brockman shows a video taken by a monitor in Edna Krabappel's classroom showing how children such as Jimbo, Kearney, and Dolph have written the answers all over their arms and stomachs. Apparently, the kids get the answer keys from Agnes Skinner in return for alcohol. Skinner organizes a meeting for parents to find a solution to stop cheating, but the only thing he is able to do is babble on and pretend to faint. Luckily, Lisa has a solution, she creates the school honor code, where every student promises not to cheat and report every cheater they see. The parents quickly agree to Lisa's idea, and Skinner says he saves the day again by fainting like he did during a battle in Vietnam.
Homer tells Marge about his old pen pal Eduardo Barcelona, and how they used to write about their dreams of the future to one and other. To help Homer, Marge contacts Eduardo and invites him to come and cure Homer's depression. When Eduardo arrives he is shocked by Homer's appearance and asks if his hair caught on fire while trapped in a candy store. He suggests they fulfill all Homer's childhood dreams as Eduardo has already accomplished most of his. Homer and Eduardo drive a fire truck, fight pirates in a play (which is directed by Llewellyn Sinclair,) and they even perform a battle scene between Captain Kirk and a Gorn from Star Trek by using many of Comic Book Guy's props for only $10.
At school, Lisa slyly persuades all the students to sign her new honor code. After several days, it looks like the new system works, even the worst students are studying now. However, she then finds out Bart was cheating all this time. And to make matters worse, she can't report him because it would mean her system failed.
After that, Homer feels great and even helps Marge to fulfill her child dream, jumping on the bed. However, there is still one dream on Homer's list left, flying like birds; therefore Homer and Eduardo decide to do wingsuit flying. However Homer is afraid to fly, but Eduardo reminds him of his childhood hero Rocky the flying squirrel. Homer then corrects Eduardo by saying the voice actress who portrayed Rocky "June Foray" was his hero. Eduardo pushes Homer out of the plane giving Homer primordial fear and panic, but when he gets used to the concept, he soon enjoys flying. Unfortunately, it ends when he flies into the tallest building in Springfield and falls down.
Meanwhile, Lisa turns crazy and tries to force Bart to turn himself in. Bart says that the only way he'd turn himself in is if he receives a sign from God. The sign is Homer, who falls on Bart after hitting the building. Bart eventually turns himself in and spends his time by working on the detention quilt with Jimbo, Dolph, and Kearney.
While in the hospital Homer says he feels calmer now that all his dreams are fulfilled; however he is really calm because Dr. Hibbert gave a lot of Morphine. Homer asks for the Morphine forever, but Dr. Hibbert tells him a person on Morphine all the time would constantly resolve in an inappropriate laughter, then he chuckles as usual. When Eduardo reminds Homer he promised to take him to the airport, he asks if he has to drop him off at the curb or come in with him. Eduardo responds by saying, "go as far as your heart takes you." Homer ends up going all the way to Barcelona with him, and Eduardo reminds Homer that he is a good friend.