How I Met Your Mother S01E06 – Slutty Pumpkin

Ted goes to a Halloween party hoping to reunite with a girl he met four years ago. Barney tries to convince him to ditch that party for a better one. Marshall and Lily go on a double date with Robin and her boyfriend.

 
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 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 the bar, and Lily notices that Robin isn't acting like she is 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, but when Carl announces Marshall as a "gay pirate" he is very confused.

Ted spends his Halloween waiting for the "Slutty Pumpkin" (a girl in a pumpkin costume with 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, she likes to call it the Tootsie Roll because it tastes like an alcoholic Tootsie Roll. Every year he waits at the same party, dressed in the same old costume, a hanging chad (because that is the one he was wearing when Ted first met her), 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, and doesn't succeed in seeing her. He thought he did, 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 alcoholic Tootsie Roll. Ted waits, but finally gives up. Robin, knowing he'd be up there, comes up to the roof, and sits and talks with him for a while at the end.

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