Halloween high jinks are afoot when Ted makes his annual trek to the same lame party in search of a girl he met there years ago.
This episode provides examples of:
- A Cappella: The music at the party is by an a cappella group.
- Ace Pilot: Barney's original costume, which is also a Shout-Out to Top Gun.
- Aloof Dark-Haired Girl:
- The hula girl, though it's justified since Barney keeps pestering her.
- Robin is gorgeous, tall and dark-haired... but very aloof to Mike.
- Chekhov's Gunman: The titular "Slutty Pumpkin" will indeed be a Girl of the Week... six seasons later.
- Coordinated Clothes:
- Lily and Marshall are a cute couple and very much in love. They like wearing matching Halloween costumes. They dress up as a not-gay pirate and his parrot.
- In a flashback, Marshall and Lily are shown being Sonny & Cher (surprisingly, Marshall as Cher and Lily as Sonny) for one Halloween.
- Barney wants his best friend Ted to coordinate their Halloween costumes. He brought two Ace Pilot costumes and wants Ted to go as his literal and metaphorical wingman. Ted defies the trope. He insists on wearing his old costume as the infamous ballot vote "Hanging Chad" because that's how the Slutty Pumpkin remembers him.
- Robin and her boyfriend joked over emails about dressing up as Hansel and Gretel. Mike thought she was serious, but Robin's part of the costume was missing.
- Costume Porn: All over the place, with this being a Halloween Episode and all. Lily's costume for instance is described by Marshall as "elaborate".
- Crazy-Prepared: The number of costumes Barney has at his disposal edges on ridiculous.
- Early-Installment Weirdness:
- Robin claims to have never played team sports, even though later this season she says she used to play field hockey and we later discover she played ice hockey as well.
- The guy in the angel costume asks for weed. In later seasons, weed would be censored to sandwiches.
- Good Angel, Bad Angel: Played for laughs when a man dressed as an angel and Barney in a devil costume try to convince Ted to pee off the roof; subverted when the angel asks if they have weed.
- Group Costume Fail: Mike didn't realize Robin was joking about dressing up as Hansel and Gretel, resulting in him being embarrassed when he shows up to the bar in costume and sees Robin wearing regular clothes.
- Guyliner: Marshall is wearing some as part of his Jack Sparrow costume. Becomes the source of the episode's Running Gag.
- Hot as Hell: Barney's second costume is as a fancy devil.
- Hypocritical Humor: Barney evokes Do Not Explain The Joke despite doing so himself.
- Kick the Dog: Barney disguising himself as the "Slutty Pumpkin" in a Penguin mascot For the Evulz.
- Mascot: Barney's third and final costume.
- Master of Disguise: Barney, even calling himself word for word as such.
- Mistaken for Gay: Marshall, though not really him but his costume. It's because of the Guyliner.
- Ms. Fanservice: The hula girl's costume is very revealing.
- The One That Got Away: Ted believes the "Slutty Pumpkin" to be his big chance at finding his one true love.
- Pungeon Master: Barney's (unsuccessful) pickup lines to the hula girl are mainly Puns.
- Romantic Spoon Feeding:
- Marshall and Lily share dinner, and Lily enjoys spoon-feeding Marshall. They later also share a dessert.
- Robin is reluctant to do any lovey-dovey stuff with Mike, but Mike wants her to taste his chicken, but she refuses. Lily tells her she should be more girlfriend-like and she attempts to share her sundae, but she likes it too much, so it doesn't really work out well.
- Running Gag: Barney's love of magic (imported from NPH) makes its first appearance.
- Shout-Out:
- Barney's first costume, the Ace Pilot, is an obvious reference to Top Gun, complete with playing Kenny Loggins' "Danger Zone" in his Big Entrance.
- Marshall's costume is Jack Sparrow.
- Marshall and Lily's costumes in Ted's flashback are Sonny & Cher.
- Ted and Marshall discussed the Ewok's Broken Base status from Return of the Jedi.
- Ted's "Hanging Chad" costume is a reference to the voting controversy in Florida during the 2000 U.S. Presidential Elections.
- Robin and her Guy of the Week were supposed to be dressed as Hansel and Gretel.
- Stalker with a Crush: Barney relentlessly pursues the hula girl.
- Stealth Pun: Because he is Ted's self-appointed wingman, Barney dresses in a literal Ace Pilot costume.
- That Came Out Wrong: "I'm not a gay pirate; I have sex with my parrot all the time!"
- Trivial Title: The titular "Slutty Pumpkin" didn't show up in this episode and will only appear for the first time in the series six seasons later.
- The Unreveal: It will take six seasons for The Reveal on who the titular "Slutty Pumpkin" is.
- Unreveal Angle: Slutty Pumpkin's face is never shown. Ted also implies that the costume was very fan-service-y, but it's shown only from back.
- Wholesome Crossdresser: Marshall and Lilly as Sonny & Cher in the flashback.
