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The title is a reference to "Portnoy's Complaint", a 1960s novel by Philip Roth about Jewish-American life.

Tom goes to a prep school.

Brittany was, of course, looking for "patronize." Fraternize is also oddly appropriate, considering their relationship and her earlier threats involving "headaches".

Brittany's little homing sequence is probably a reference to the Clothes Hunt scene in "Terminator."

The "Vexer" resembles the Dodge Viper, but good luck getting that car for twenty grand.

Jodie says "no pun intended". Daria replies "none taken". This reply is usually given when people say "no offense intended" to appologize for something said that may be offensive. Since what Jodie's saying at the time is probably offensive to Daria she may be working in a little shot at her.

This is the third time Daria and cheese-fries have been connected.

Daria's comment about "being tired of that head anyway" might be a reference to Jeeves of "Men in Black", an alien who grows a new head when it gets blown off in the film. It might instead be a reference to the old AD&D standard Llarnian monsters, but that's far less contemporary. Ditto the mythological hydra.

Daria's locker at the end of the episode is number 251.