The TGS team is thrown into disarray when someone anonymously trash-talks Jack to the New York Post. Meanwhile, Pete gets his arm trapped in a vending machine.
This episode contains the following tropes:
- Bad Liar: Kenneth is uncomfortable with lying, and is comically bad at it.
- Bait-and-Switch: Tracy comes in asking Liz about something she said being in the paper. Liz (and everyone else) thinks he's referring to the comments about Jack, but he's actually referring to a Cathy strip. It turns out Liz did say "Chocolate, chocolate, chocolate! Ack!"
- Batman Gambit: Jack knows Liz well enough to know how to make her crack and admit to trashing him.
- Bottle Episode: This episode takes place entirely in the offices and hallways of 30 Rock.
- Distracted by the Sexy: The entire office, except for Liz, is riveted by MILF Island. Even Dick Cheney is a fan.
- Elimination Catchphrase: MILF Island has one: an appropriately blunt "get off of MILF Island".
- Freudian Excuse: Jack claims to have one as a result of a childhood stutter, although it's later revealed that he made it up.
- Hope Spot: Pete makes a desperate effort to get unstuck from the vending machine by throwing items, like his shoes and wedding ring, at a nearby phone's keypad in order to call a random number. Improbably, it works...too bad that random number turned out to be Pete's own office.
- I'm Not Here to Make Friends: Both Liz and a MILF Island contestant say this line at the same time.
- Lowest Common Denominator: In-universe, Liz calls MILF Island this, and not without reason. As a couple of cutaway gags show, however, TGS is just as guilty.Tracy: (as a scientist in a TGS sketch) Someone put too many farts in this engine! It's about to explode!
- Manipulative Bastard: Jack made up a tragic backstory as a stutterer deemed a "class A moron" in order to guilt Liz into confessing.
- One Steve Limit: Averted. The final two contestants on MILF Island are named Debra and Deborah, two variations of the same name. In this case, however, Deborah is pronounced as "duh-BOHR-uh".
- Show Within a Show: The eponymous MILF Island, a riff on Survivor that was mentioned in a previous episode, is omnipresent here. The events of the episode frequently mirror the events of the MILF Island finale.
- Something Only They Would Say: Jack knew that Liz was the anonymous source from the start due to the use of the word "poo".
- Speech Impediment: Jack claims to have had a debilitating stutter as a child, resulting in his being designated a "Class A Moron" and stuck in the special class. At the end of the episode, it's revealed that he never really had one.
- Vengeful Vending Machine: Pete gets his arm stuck in one after he tries to steal a dangling snack, which keeps him incapacitated for the rest of the episode.