When Bart stares open-mouthed at what is revealed to be Shauna's arm in Moe's Tavern, the view before the camera zooms out is a sight gag on the movie poster from the 1967 comedy-drama film The Graduate, which also features music by Simon & Garfunkel.
Squeaky-Voiced Teen's nametag says "Steve" at The Brown Burrito, even though outside references state that the Squeaky-Voice Teen's real name is Jeremy Freedman.
Marge is kind to Jimbo, Dolph and Kearney in this episode, however in "The Blue and the Gray," Jimbo shouts an insult at her, and Marge backs up the car to tell him off, and the bullies run away. Marge being nice could have been because she had forgiven him, forgotten about the insult, or did not know that it was him that insulted her.
In the International/online version of this episode, the title screen gag is repeated from the episode "Elementary School Musical," and the chalkboard gag is "Teacher does not have to pay an "Ugly Tax"."
When Homer is saying "Watch whatever you want...," Milhouse is in front of a Transformers of the Caribbean movie poster and Bart is standing next to him. Then Homer, Bart and Milhouse keep walking. Afterwards, Homer looks round at them, but the boys are in exactly the same position as they were.
Jimbo mentions that Bart has two baby teeth. However, he lost his last baby tooth in "Fat Man and Little Boy."
When Jimbo picks Bart up to see if he's a good chaperone for Shauna, he wipes a temporary tattoo of Bart's arm. The tattoo was not there before he wiped it off, and is not there when Jimbo puts Bart back down on the ground.
When Homer looks out the window to see Jimbo holding Bart upside-down by his ankles, as the shots change, the treehouse moves place slightly. The window also changes design.