The first special filmed and produced after ''The Adventures of Pete & Pete'' was promoted from shorts of 60 seconds to specials of 30 minutes, originally aired in February 9th, 1991.

Big Pete competes with school line painter Mr. Beverly for the heart of math Teacher Miss Fingerwood, a matter complicated by Pete's arch enemy Openface, Ellen's feelings for Pete, and Pete's murder of the school mascot Edna the fighting squid.

!!"This is 'Valentine's Day Massacre'. And these are its tropes":
* AccidentalMurder: Edna meets her end thanks to a stray discus.
* TheBully: Openface.
* TheCameo: Creator/RichardEdson (original Music/SonicYouth drummer) as Mr. Beverly.
* ChuckCunninghamSyndrome: Openface, who is promptly replaced by Endless Mike in the series proper. Justified, though, because the creators didn't expect Nickelodeon to pick the specials up to be a full TV series.
* ColdBloodedTorture: Downplayed — When looking for some of big Pete's weaknesses and a particular secret, Open Face and his gang go towards little Pete, and they force him to reveal it, but since he is more loyal to his older brother, rather than talking, they go staright up with black markers and draw all over Petunia.
* DisproportionateRetribution: Openface dedicated himself to making Pete's life miserable...because Pete stopped him from electrocuting a chihuahua.
* EditedForSyndication: As it happened with the other 4 following specials, this is compounded normally as the ''Pilot Season'' of the whole TV Series. Once it was picked up as a whole series, the theme song, opening credits and some music were added for its following rerunning TV broadcasts, to complete the first season.
* EmbarrassingFirstName: Openface's first name is Eugene. Big Pete can’t help but laugh upon finding out.
* FirstAppearance: Syd Straw as Ms. Fingerwood, who later showed up next in "''Hard Day's Pete''".
* KickTheDog: Openface passed the kicking stage and skipped right to electrocuting them.
* LoveDodecahedron: Pete and Mr. Beverly like Miss Fingerwood, who likes Mr. Beverly back, and Ellen likes Pete who starts to return the feeling.
* MadMathematician: Miss Fingerwood has not exactly the 'Mad' part of it, but... she is clearly obsessed, since her life is involved entirely with Math.
* ManipulativeBastard: Openface, who plays both Mr. Beverly and Ellen like a fiddle to get exactly what he wants.
* PrecociousCrush: Big Pete was only 13 years old when he developed a crush on Ms. Fingerwood.