- After an alcohol-induced blackout, Ted awakens to find a strange woman and a pineapple in his bed.
- In 2030, Ted admits to his kids that he doesn't remember all the stories from his past, with what he and Marshall call "the pineapple incident" being one of the more fuzzier ones. In late 2005, in the still short time their group of friends has included Robin, she is onto yet another guy (this time a multi-multi-millionaire) while Ted has barely had any women. Barney thinks it's because Ted over-analyzes every situation. So to lower Ted's inhibitions, Barney, Marshall and Lily think it would do Ted some good if he downed all five shots that Carl the bartender has concocted for them. To prove a point, Ted does down all five believing they will have no effect on him. But the next thing he remembers is the next morning waking up in his bed, with a sprained ankle, next to both a pineapple and a brunette woman whose face he can't see as she is face down on the pillow. Marshall, Lily and Barney are only able to fill in a part of the puzzle. As the four go on a quest to figure out the remainder of the puzzle (with Marshall fixating on the pineapple), the journey may start with the message on Ted's right arm. Ted believes that perhaps Robin, who was on a date with her multi-multi-millionaire boyfriend for the evening and who Ted called all evening in his drunken stupor, can also provide some information on what happened.—Huggo
- After sucking down a quintet of shots at the bar, Ted blacks out. He wakes up the next morning with a sprained ankle, a burned jacket, a phone number written on his arm, a pineapple on his dresser, and an unknown woman face down in his bed. With the help of his friends, Ted attempts to piece together precisely what happened the night before.—Seth Christenfeld
- Ted wakes up with a sprained ankle, a burned jacket, a phone number written on his arm, a pineapple on his dresser, and an unknown woman face down on his bed. The gang attempts to trace the previous night's events.—sid
- Barney, Marshall, and Lily criticize Ted for overthinking every aspect of his life (Robin is going out on a date with a billionaire, when she insists that he is only a 100 millionaire. They are going to a charity dinner costing $1500 per plate), rather than simply acting on a whim. Barney convinces Ted to take five shots of 'Red Dragon' (a special blend by Carl the Bartender at McLaren's); Ted claims that he can still function cognitively even under the influence of the alcohol, but shortly afterwards he blacks out. He wakes up the next morning with a girl he doesn't remember beside him in bed, a pineapple on his nightstand, and a sprained ankle. He also finds out that his coat has been partially burnt.
Ted asks Marshall and Lily about the night, and Marshall and Lily tell him that he sang along with the jukebox in the bar while standing on a table. He also repeatedly drunk dialed Robin, who was on a date with a wealthy businessman. Ted claims that he has been vomit free since 1993. He sings to her over the phone with a song playing on the jukebox. He fell off the table (explaining the sprained ankle), and Marshall and Lily took him up to his bed. However, they are surprised when Ted asks about the girl on the bed and can shed no light on the pineapple or why Ted's coat is burnt. Ted calls Barney, thinking that he might know what had happened, and finds him sprawled in their bathtub still dressed in his suit.
Barney recounts that Ted reappeared at the bar around 1 a.m., but when he began to call Robin again, Barney lit Ted's coat on fire. After some more fun, he puts Ted back into bed, and similarly has no idea who the mystery girl is.
Ted finds that someone wrote on his arm, saying to call the number if Ted was found passed out somewhere. Ted calls the number and reaches the bartender, Carl, who fills in some more of the story: Ted again returned to the bar at 3:00 a.m., but Carl refused to serve him. Ted told Carl the meaning of the word "karaoke" (Japanese for empty orchestra, which Ted finds hauntingly beautiful) and that he wanted to go see some penguins at the zoo (that's when Carl writes his number on Ted's arm, in case his ends up in the sewers), then suddenly called someone (presumably Robin) and told her come over and do something "crazy". Based on this information, Marshall, Lily, and Barney believe that the mysterious girl in Ted's bed is actually Robin, but as Ted goes to wake her up, Robin calls and tells him she is coming over to discuss the previous night.
The girl in bed, Trudy (Danica McKellar), wakes up, and explains her side of the story: Ted had caught her eye during his drunken dancing, and they exchanged numbers in the ladies' room of the bar (which Ted used by mistake). She told Ted the meaning of the word "karaoke" and about her love for penguins, explaining why Ted later mentioned these things to Carl. It was she whom he later called and invited over, not Robin. Ted tells Trudy to hide when Robin comes over to talk, and Trudy leaves via the fire escape before Ted can show her to Robin to prove that he has moved on and that they are still only friends and this is not weird between them. Future Ted explains that Trudy never responded to his subsequent message, and he never did work out where the pineapple came from, but it was delicious.
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