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.
Barney chooses between wearing suits and sleeping with a sexy bartender. Meanwhile, Ted gets ever closer to meeting "the mother".
- Old Ted started the night by telling the kids that you never know when you're going to meet someone special -- you just look up and there she is. Young Ted, roaming the halls of the college campus, looked up and saw Cindy (played by Rachel Bilson -- no relation to Barney's boss, Bilson, as far as we know). After busting some underage frat guys with beer, Ted and Cindy chatted over those very beers. Cindy, a Ph.D. student, confessed to Ted that she remembered him from his ill-fated first day on campus. She was in the economics class he mistakenly tried to lecture on architecture. (Remember at the end of last season, Old Ted told us the kids' mother was in that class).
Cindy thought Ted was a complete idiot. He asked if she ever dates complete idiots.
"Almost exclusively," she said.
Ted was telling the gang all about Cindy when they heard a loud crowd outside the window. It was a line (mostly dudes) at McClaren's. They went down to discover that a hot new, blonde bartender was the reason. Stacy Kiebler played the new bartender, mixing drinks while Warrant's "Cherry Pie" blasted in the background.
Lily's first reaction, "Aww, the sidewalk is going to smell like pee-pee now."
Barney said his remaining wish was to land a hot bartender. He went through the list of the occupations of the women with whom he's scored with, but never a hot bartender. Barney went off to try a shot at the bartender, looking to take his "alpha-dog" place in their relationship.
Marshall showed up and tried to convince Lily he didn't think the bartender was any hotter than her. Barney went up to the bartender, who immediately put him in his place. After being overly nice to other guys (and getting tipped nicely in exchange) she simply asked Barney if he was going to order something, "or just stand there looking stupid all night." (It's worth noting now that Barney, of course, was wearing a suit).
Meanwhile, Ted was at Cindy's apartment and said he got the feeling he was "exactly where he was supposed to be." Ted looked at some decorations on a shelf and Old Ted told the kids it was the first time he'd ever seen their mom's little yellow bus, which was on a shelf right behind them. Cindy came back into the room and Ted mentioned the bus. Cindy said it belonged to her roommate.
There was Ted, in his future wife's apartment. He asked Cindy what her roommate was like. Cindy's first description of the woman Ted would one day marry: "She's a whore."
Cindy went on to say she thought her roommate was a dominatrix, but then admitted what she'd said wasn't true. Cindy confessed that she had a bit of a roommate complex because all guys fall in love with her roommate. Ted promised he wouldn't do that. Old Ted said, "Oops."
The gang back at the bar was still hung up on the bartender. Marshall was still refusing to admit she was hot, and Barney was still wondering why he got the cold shoulder. Marshall found out that her last three relationships were with Wall Street guys and they were all jerks, thus she vowed to never date a guy who wears a suit. Barney thought it would be easy for him to stop wearing suits. He announced he would stop wearing -- wait for it (even though we all knew he was going to say "suits") -- suits.
Ted was at dinner with Cindy, who was unloading her roommate complex, telling Ted about the weird things her roommate does, including painting robots playing sports. Ted said that was weird, but Old Ted admitted he thought that was actually kind of cool. Cindy said her roommate also has a habit of making breakfast foods sing showtunes, another thing Ted agreed was weird -- before Old Ted interrupted with, "Your mother's rendition of 'Memory,' as performed by an English muffin is, to this day, the most hauntingly beautiful thing I have ever heard."). Ted told Cindy he was sold, and hated her roommate -- whom he'd still never met and would one day marry.
Back at the bar the next night, Barney was wearing a T-shirt and talking to the hot bartender, who apologized for misjudging him. Ted showed up and said his second date with Cindy was not great because Cindy didn't want to date him anymore, because the school's rule forbade it. Marshall told Ted to just let it go with Cindy.
Barney was also having trouble letting go of his suits. At home, the suits were whispering to him. When Marshall came to the bar the next day in a suit, Barney touched it and smelled it as if it were a fine wine. Back home again, Barney pulled a suit out of his closet and heard a whisper, "Suit up!" Barney donned it, but as he prepared to take it off, it ripped.
Barney raced the suit over to his personal tailor, TV's Tim Gunn, who tried to save the suit, but could not make it work. He said the buttons from Barney's suit could be used for another suit -- like an organ donor. "Your suit's death could mean another suit's life," Tim Gunn told Barney.
Barney cried while telling Tim Gunn to go ahead with the button transplant.
Back at the bar, Barney held an urn and said they'd cremated the suit. Still, he wasn't going to give up his quest for the hot bartender, saying that his suit had given its life in this effort.
Ted took note of Barney's fortitude and decided he wasn't going to give up on Cindy so easily. What if she was his future wife? He gave Barney's urna kiss and took off.
Barney told the hot bartender about his friend who died, and she decided to end her shift early to comfort Barney.
Lily pressed Marshall to admit the bartender was hotter than her. "She's a goddess," Lily said. "Her legs go for miles. And that ass? I would wear that thing for a hat!" Lily then admitted that the bartender popped into her head the previous night a couple of times. Marshall was upset that Lily thought the bartender was hotter than him.
Robin, who finally let loose with her jealousy of the hot bartender, got up and claimed that the bartender wasn't even hot -- "it's circumstantial hotness." She went behind the bar and started tossing pouring shots to the tune of "Cherry Pie," before the barkeep kicked her out.
Ted went to Cindy's apartment. Her roommate was in the shower, so they went into Cindy's room to talk. Ted tried to convince her to keep dating him because he felt like their paths were destined to cross. He looked around her room to see all the things they have in common. He found a CD he knows hardly anyone has. It was her roommate's. He saw a book he loved, but it was a gift to Cindy from her roommate. He saw a bass guitar and said he always wanted to date a woman who played bass -- and he realized before he finished saying it that the bass belonged to Cindy's roommate. "She's in a band," Cindy said. Ted thought that was cool.
Cindy kicked Ted out, and he didn't meet his future wife that night. But he did catch a glimpse of her foot as she slipped into her room after her shower. Ted also accidentally left behind the yellow umbrella, telling the kids their mom got her yellow umbrella back.
Barney brought the bartender back to his apartment and she said she'd make him feel all better. She opened a door she thought was the bathroom, but it was a closet packed with suits. She asked Barney to choose between her and the suits.
He pondered the question, then broke into the long anticipated musical number for this special 100th episode, "Nothing Suits Me Like a Suit."
The seemingly grand finale, Broadway-inspired number ended with a full chorus, including Marshall, Lily, Ted and Robin, backing Barney. As the final words were sung, and Barney proclaimed once more than "nothing suits me like a suit," he stopped and said, "Then again, she is kinda hot."
Cut back to Barney in his apartment, where he told the bartender, "I choose you." He vowed to get rid of all his suits the next day. As they kissed and fell into bed together, he turned to his open closet and whispered to the suits, "You guys are fine."