- Barney chooses between wearing suits and sleeping with a sexy bartender. Meanwhile, Ted gets ever closer to meeting "the mother".
- A beautiful woman named Karina starts working as a bartender at MacLaren's. Robin believes Karina's hotness is all circumstantial. Many men are mesmerized by Karina, but none more so than Barney, who has never slept with a bartender. Barney has a plan to woo Karina, but Karina, who has so far treated all the patrons at the bar like her best friend, is immediately turned off by Barney. Marshall learns it's because she previously had a bad experience with a man who worked on Wall Street, so now she immediately is turned off by anyone wearing a suit. Can Barney give up his suit wearing ways to impress Karina, or put aside his suits long enough to sleep with her? Meanwhile, Ted has started dating Cindy, a student at the university. Cindy breaks it off with Ted when she learns that the university has a strict no professor-student dating policy, which means that if they are caught, Cindy could lose her scholarship and Ted could lose his job. But something about Cindy makes Ted feel that he has to be with her at that time. In 2030, Ted tells his children that that something is Cindy's roommate, who Ted has not even met yet.—Huggo
- Future Ted again expounds on the unknowable nature of destiny, and tells the kids about the time he almost met their mother. After leaving class, Ted intercepts a series of fraternity brothers inviting a woman, Cindy (Rachel Bilson), up to the roof to drink. Confiscating the alcohol, he sits down to drink the beer with her, a Ph.D. student roughly his own age to whom he can relate. Cindy recognizes Ted from econ 305, and says he was a cute idiot. He asks her out, and when he goes to pick her up, it turns out Cindy has serious issues with her roommate (whom Future Ted reveals to be the Mother); her dates keep falling in love with her roommate, and her roommate's strange habits annoy Cindy. Ted promises Cindy to never fall in love with her roommate ("Oops," says Future Ted).
During the date, Cindy explains more about the roommate's strange habits she dislikes that Ted secretly thinks are awesome, such as how the Mother paints pictures of robots playing sports and has breakfast foods singing show tunes. Future Ted reveals the painting of robots playing volleyball is still hanging in the house and that an English muffin singing "Memories" is the most hauntingly beautiful thing he has heard to this day. Even though she complains about her roommate throughout the evening, Ted wants to continue dating Cindy.
After the date, Cindy tells Ted she can't see him again, blaming the University policy preventing students and lecturers from fraternizing, because she fears it could cost her her scholarship. Ted rationalizes her decision is for the best, especially as the others point out that Cindy's future and Ted's job are in jeopardy. Ted goes to Cindy's apartment and tries to persuade her to go out again, unwilling to miss the chance she is the right woman. She takes Ted to talk in her room because her roommate is about to leave the shower. To convince Cindy that their paths are meant to cross, he picks out items from her room which show how much they have in common (The bass guitar, The unicorns (album), World's end by TC Boyle). Cindy reveals all three objects are really connected to her roommate. Frustrated that Ted is already more compatible with her roommate, Cindy tells him to leave. Ted does not meet her roommate, but on his way out he catches a glimpse of her leg as she disappears into her bedroom. Ted forgets to take the yellow umbrella he brought with him, revealing how their Mother gets it back.
MacLaren's has hired an attractive female bartender (Stacy Keibler), and Barney seeks to add her occupation to his list of conquests (he has never scored a hot bartender till date), but she doesn't like men in suits (Barney started being all alpha male on her, but she turns the tables on him and doesn't give her any attention), having dated insensitive Wall Street losers. Barney is forced to choose between the girl and the suits. For a while he dresses casually, convincing the bartender she misjudged him. At a point when Marshall is wearing a suit and Barney is not, Barney gets overly affectionate with Marshall's suit. Later, Barney sneaks away to the bathroom to wear his suit, where he accidentally rips the back. The suit is damaged beyond repair, but his tailor, Tim Gunn (himself), transplants the buttons to save another suit and Barney cremates the remains.
Meanwhile, Lily, Marshall, and Robin argue about the bartender's attractiveness. Robin is jealous, and gets behind the bar to show how the location amplifies natural beauty (circumstantial hotness); Carl (Joe Nieves) soon kicks her out from behind the bar. Marshall insists the bartender is not that attractive, saying Lily is the most beautiful woman he has ever met. Lily tries to get Marshall to say she is not as beautiful as the bartender, and eventually even implies that the bartender is better looking than Marshall, upsetting him a little.
With the urn of suit ashes and his real tears for his lost suit, Barney convinces the bartender to go to his apartment, where she accidentally opens his closet full of suits and realizes he deceived her. She forces him to choose between her and his suits. She is angry as they are shown leaving the building and Barney breaks into song, professing his love of suits (Nothing Suits Me Like A Suit)-only to choose her at the end of the song when he realizes "she is pretty hot." He tells her she is more important than the suits and they will go first thing in the morning. As they fall into bed, he whispers, "You guys are fine" to his suits, which move slightly as if breathing a sigh of relief.
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