Plot
Marshall and Lily are very excited about Halloween, and have received their costumes in the mail. Marshall has decided to dress up as Jack Sparrow, and Lily as a green parrot. They really hope to win the costume contest at the bar and win the prize of a $50 gift certificate having spent $100 dollars each on their costumes. They invite Robin and her new boyfriend Mike. Although Robin told them neither she nor Mike were dressing up, Mike comes dressed as Hansel, and asks Robin why she isn't dressed as Gretel. They go down to McLaren's, and Lily notices that Robin doesn't appear interested in Mike, even though Mike is obviously interested in her. Lily tells Robin that in order to avoid losing Mike, she is going to have to do "couple things" (such as share food, hold hands, etc.) and not send Mike the wrong signals. Robin tries, but she doesn't succeed, and Mike breaks up with her. Marshall and Lily do indeed win the costume contest.
Ted spends his Halloween waiting for the "slutty pumpkin" (which has strategically carved holes) that he met in 2001. Ted really likes this girl, but he lost her phone number when Lily gave away the Kit Kat that he had written the girl's phone number on. All he knows about this girl is she has studied penguins and enjoys making a drink that combines Kahlúa and Root beer which she likes to call "The Tootsie Roll". Every year he waits at the same party, dressed in the same old costume, a hanging chad, hoping the "slutty pumpkin" will be there.
Barney wants him to come to a Victoria's Secret party on a yacht, but Ted stays at the party, even though the "slutty pumpkin" doesn't show up. (He thought she did at one point, but it was Barney, who was already in his third costume of the night, intentionally trying to fool him by dressing as a penguin and making "the Tootsie Roll".) Ted finally gives up and goes to the roof to think. Robin, knowing he'd be up there, comes up to the roof, and sits and talks with him for a while.
Music
Kenny Loggins - "Danger Zone"
Nada Surf - "Inside of Love" (not on DVD release)
Cultural references
Marshall is dressed as Captain Jack Sparrow from the Pirates of the Caribbean films. Throughout the episode, it is pointed out that Marshall is wearing eyeliner, to which he replies, "weirdly hot, right?". Also, Robin notes that there are many guys dressed as "gay pirates" because they are all wearing eyeliner. Marshall tries to refute this by saying, "I have sex with my parrot all the time," referring to Lily, who is dressed as a parrot.
Marshall references Star Wars Episode VI: Return of the Jedi when he says "The rebellion would have failed without Ewoks".
In the 2001 Halloween flashback, Lily and Marshall are dressed as Sonny & Cher, respectively (Lily as Sonny and Marshall as Cher).
Mike dresses as Hänsel (with Robin supposed to be dressed as Gretel) from the classic fairy tale Hänsel and Gretel.
Ted, since 2001, has dressed as a hanging chad as in reference to the voting controversy in Florida during the 2000 U.S. Presidential Election. Lily complains that no one understands Ted's costume anymore, which Marshall says offers a sad commentary about society.
Barney's first costume (of three that night) is that of a fighter pilot, with many obvious references to the film Top Gun. When he shows up at Ted's apartment, he has a boombox playing "Danger Zone" by Kenny Loggins. Barney wants Ted to be his wingman and tells him to "flightsuit up," but Ted refuses, at which point Barney quotes the film, saying, "Oh, you're dangerous, Maverick. Your ego's writing checks your body can't cash."
Barney says that he can get Ted and him into a Victoria's Secret party, which they eventually do go to in "The Yips".
Ted waiting up all night on Halloween for the Slutty Pumpkin to appear is reminiscent of Linus waiting for the Great Pumpkin in It's the Great Pumpkin, Charlie Brown. At the end, The Shagarats sing the Peanuts theme, "Linus and Lucy".
Ted says, "are we playing I never because all that's left is Peach Schnapps", referencing the drinking game I never.
Continuity
In the Season 5 episode "Bagpipes", it's shown that Robin hates nicknames and never uses them. But in this episode she calls Ted "Teddy Boy".
Robin said that she didn't play team sports growing up. But in the season 4 episode "Happily Ever After", she is shown on a hockey team. She also mentions how she missed her prom because she had a field hockey game the next day.
In "Zip, Zip, Zip" Marshall says that Lily has never peed in front of him before. But in this episode Marshall goes with Lily when she has to pee.
Barney's Top Gun line is re-spun by Lily in the Season 6 episode "Baby Talk".
Barney's Blog
In his blog, Barney describes his Halloween routine, briefly (and vaguely) recaps the events from the year before, and ends the blog with a quiz to see if people were able to figure what happened.
Clicking on the 'Solution' button reveals what actually happened, at least according to Barney.
Recurring elements introduced in this episode
Barney adapting his name into a nickname — e.g. in this episode he says that "The Barnacle" will stick to the yacht with the Victoria Secret party, he calls his apartment "The Fortress of Barnitude" (a reference to Fortress of Solitude).
Marshall and Lily's nicknames for each other: Marshmallow and Lilypad.
Lily's frequent urination problem
Production
In an interview for Television Without Pity series co-creator Craig Thomas said that every season the writers discuss at length how the Slutty Pumpkin might factor into the mythology of the show. He describes Ted waiting optimistically as being like Lloyd Dobler (portrayed by John Cusack) from the film Say Anything.
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