On a rooftop, Luong Lao Shi, better addressed as Gramps, is showing Jake the landscape of New York City and tells him that it is his responsibility to protect all magical creatures living within it. Fu Dog tells Jake that if he can make it in NYC he can make it anywhere but Gramps warns that Jake has to master his dragon powers first. Jake attempts to show off his skills and shape-shifts into a dragon and hovers above them. As Jake brags about himself, he unwillingly returns to his human form and nearly falls to his death.
Later, in Central Park, Lao Shi continues on with his lesson. Gramps warns Jake that he must obey him without hesitation and Jake promises to do that. At that moment, Fu tracks the smell of the Huntsman and Jake realizes that he's after the unicorns. The group soon finds the Huntsman hiding in the bushes, preparing to slay the mythical horses and Gramps says that Jake must do this fight alone.
Jake shape-shifts his head and prepares to breathe fire at the Huntsman, but the fire comes from the wrong end. As Jake apologizes, he realizes his pants are on fire and rushes to the river to put the fire out, revealing himself to the Huntsman. Jake transforms the rest of his body into dragon form and prepares to take battle. But then a new fighter appears -- Huntsgirl—and the two battle, but due to his inexperience Jake is easily defeated. Gramps creates a wall of fire, saving Jake and forcing the Huntsclan to retreat. Gramps says that he needs more training and tells him to go to the rooftop after class the next day.
Next day, at Millard Fillmore Middle School, Jake is attending his mythology class, which is being taught by Hans Rotwood—a human scientist who believes in the existence of magical creatures. Hans gives the class information that presumes that magical creatures exist, but Trixie Carter claims that they don't. After school, Spud and Trixie try to invite Jake to go skateboarding with them, but he has to go to work at Gramps' store. As he leaves, he clashes against the new girl -- Rose, who has a dragon-shaped birthmark on her wrist.
At the store, Jake finds out that his training is to do chores—such as cleaning the toilet, doing the laundry and washing the floor. After hours of doing chores, Jake returns home where he talks to his mother, Susan about how Gramps might be crazy and wishes to be normal like his father, Jonathan, who's unaware that he married into a family of magical reptiles. Next day, as he leaves school, Jake meets Rose again, but his thoughts are interrupted by Trixie and Spud, who invite him to go skateboarding. Jake says that he has to help his grandfather, but then a fairy arrives, giving him a letter from Lao Shi that reminds him of his chores so he decides to skip training.
Hours later, Gramps and Fu Dog are at the rooftop still waiting for Jake to return. They're subsequently attacked by Huntsgirl and Huntsman who captures Gramps while Fu Dog manages to escape into the sewers. Fu Dog goes to Jake's house where he tells him about the attack. Jake shapeshifts to his dragon form successfully and flies with Fu Dog to the rooftop. He fights against Huntsgirl and as he does so, he finds out that his chores were actually training. In the middle of the fight, Jake wraps his tail around Huntsgirl's arm, removing her glove and revealing her dragon-shaped birthmark (revealing to the viewers that she is Rose, though Jake doesn't notice the birthmark).
Huntsman prepares to hit Jake with a plasma ball from his staff, but Jake uses his fiery breath to send him flying into another building, forcing Huntsgirl to retreat. Without the enemy around to find out about his true identity, he reverts to his human form and is congratulated by Gramps.
- Dante Basco as Jake Long
- Keone Young as Luong Lao Shi
- Kittie as Trixie Carter, Courtney
- Mae Whitman as Rose
- Amy Bruckner as Haley Long
- Lauren Tom as Susan
- Jeff Bennett as Jonathan Long, Huntsman
- Charlie Finn as Spud
- Paul Rugg as Hans Rotwood
- John DiMaggio as Fu Dog
- The title is a reference to the 2003 comedy film Old School, directed by Todd Phillips.
- Rose quotes The Karate Kid when she yells "Hi-ya!".
- Rose kicking Jake is a reference to Bugs Bunny kicking a bucket in Looney Tunes.
- This episode introduces the main characters, Jake Long, Luong Lao Shi, Fu Dog, Spud and Trixie as well as the villains, Huntsman, Hans Rotwood, and Rose/Huntsgirl. Courtney, Rose's friend, also makes her debut.
- Rose and Jake will remain unaware of each other's identities as the American Dragon and Huntsgirl until the season finale, "The Hunted", when Jake reveals his identity to her.