As newlyweds Hercules and Megara move house, Meg finds her husband's old high school yearbook, detailing all the messes Herc got into as a teenager.
This episode includes examples of the following tropes:
- Big "NO!": Hercules over Meg finding some embarrassing pieces of his past.
- Clip Show: The show consists of a frame story of Meg reading the yearbook, with flashbacks to various episodes based on the photos.
- Death Glare:
- Hercules to Phil over not keeping his mouth shut.
- A displeased Icarus and Cassandra both give one to Hercules to show how peeved they are at him for trashing the entire school on their graduation.
- Embarrassing Old Photo: Both Hercules and Megara's yearbooks contain a number of photos they would prefer the other (or really anyone) never see. The viewer gets to see some of Herc's, but not Meg's.
- Grand Finale: The episode takes place after Hercules and Megara got married sometime after the end of the movie.
- Hypocritical Humour: Near the end, Meg comforts Hercules over the shame he has from his teenage years, only to get embarrassed herself when he found out about her time in high school.
- I Was Quite a Fashion Victim: Herc gets ahold of Meg's yearbook, which we don't see.Hercules: Look at your hair!Meg: That was the style of the time.
- Irony: After all the times people doubted her visions, Cassandra got a job on the Oracle Friends Network and is famed as "the Psychic Cynic to the Stars."
- Lampshade Hanging: Meg commenting on the various episodes she reads about, particularly the one about Galatea.Meg: You made a woman out of clay?
Hercules: I was a teenage boy. It seemed like a really good idea. - Laser-Guided Karma: After all his posturing and goofing off, Adonis turns out to be one credit short for graduation and will have to attend summer school. To add further insult to it, he's the only student of the group facing this, and it's announced in front of everyone.
- Misery Builds Character: Meg points out that Herc's "awkward phase" made him the hero he is today.
- Nothing Is Funnier: Everything embarrassing in Meg's yearbook is only mentioned, never seen.
- Old Shame: In-universe. Hercules looks back on his younger days as being "that geeky loser" paling in comparison to the hero he is now.
- Pep-Talk Song: When her husband tells her he didn't want her to see his less-than-stellar past for fear that it would eclipse everything he's accomplished, Meg sings "The Man That I Love", which tells Herc she still respects him and says that he should look at his high school years as a growing period.
- Screw This, I'm Outta Here: After Hercules arrives, Phil insists that Meg made him talk and then makes a run for it.
- Self-Made Man: It revealed that Icarus made a fortune by going into manufacturing like his father before him. He's the Wax Wing King.
- Ridiculously Successful Future Self: According to Phil, both Cassandra and Icarus made names of themselves after graduating from Prometheus Academy, as mentioned above.
- Icarus became a famous inventor after going into manufacturing with his father, earning the name, "Wax Wing King".
- After joining the Oracle Friends Network, Cassandra became a renowned psychic.
- A Taste of Their Own Medicine: After Herc realizes what Meg got ahold of, he sends Hermes to find her high school yearbook. It contains its own trove of embarrassing information.
- Tempting Fate: Meg scoffs at the idea that her "boy scout" husband could have caused Phil a lot of trouble. Phil tells her that, yes, Herc had a lot of growing pains.
