Luke (Scott Patterson) is called in to Stars Hollow High to see the principal, who tells him that Jess (Milo Ventimiglia) is at risk of being held back a year if he does not improve his attendance and grades.
However, she is unable to teach Jess effectively as he distracts himself with magic tricks, making book recommendations to her and convinces her to take a break and go get ice-cream.
In an essay within Screwball Television: Critical Perspectives on Gilmore Girls, the author writes that "so much of this episode's running time is devoted to the education of its audience", noting "over two dozen" allusions to films.
The choices of The Yearling and Babe are said to remind the audience of Rory's youthfulness, in contrast to the mentions of Crimes and Misdemeanors to evoke Jess' personality.
Club says this episode, along with the following episode "Help Wanted", is the "necessary conclusion" to the show's arc where "Jess annoys everyone" and "Lorelai is weirdly insensitive and unlikable about it", but does not find Jess' "typical bad boy" persona convincing as "the show won't allow him to be truly off the rails, and won't allow his life to be truly miserable".
Though saying that the episode "only partially succeeds at unraveling" Jess, Sims compliments Lauren Graham's display of "complicated feelings with great subtlety" and Scott Patterson's portrayal of panic in the scene where Luke gets angry at Lorelai.
[3] An article in Bustle describes the short film as "hilariously awesome" and the most "impactful" of Kirk's "prolific moments" across the series.