After his best friend Marshall proposes to his long-term girlfriend, Lily, Ted solicits help from his friend Barney to find 'The One' for his life. He manages to get a date with Robin, a girl he met at his usual neighborhood bar, but threatens to scare Robin away when he accidentally reveals his love for her on the very first date. Meanwhile, Marshall accidentally hits Lily in the eye with the champagne stopper after they get engaged, forcing her to wear an eyepatch. The phrase olive theory is m
Ted agrees to deviate from his usual schedule by accompanying Barney on an unexpected trip to the airport. The excursion ultimately leads the two friends to Philadelphia, where they encounter difficulties with airport security. Meanwhile, Lily and Robin go out for drinks, but Lily becomes jealous when she is not as successful with men as Robin is, for which she blames her engagement ring. Marshall travels between both situations in an attempt to rectify the group's problems.
Ted's continuing search for 'The One' leads him to look into his past to rekindle old flames. Unfortunately, the woman he is thinking of is the same woman he broke up with years ago on her birthday, and she still holds a grudge. Meanwhile, Barney dares Robin, the anchor of Metro News One, to slip questionable words or phrases into her daily newscast in return for money. Despite this, Robin begins to appreciate the importance of her job more.
Robin invites the group to a nightclub, but Marshall and Lily decide to host a wine and cheese party in an attempt to act more mature. Marshall and Lily quickly grow bored, however, and escape their own party in order to join the rest of the group at the nightclub, where they discover Robin outside, unable to gain re-entry into the club. Meanwhile, Ted and Barney experience unforeseen events while dancing.
Marshall and Lily are excited to participate in the couples costume competition at their usual bar. On the other hand, Robin's refusal to dress in a couple costume with her boyfriend puts stress on their new relationship. Meanwhile, Ted makes his annual visit to the rooftop Halloween party in search of a girl that he met four years ago.
Robin directs a skeptical Ted to an online matchmaking service with a 100% success rate. When the service gives Ted zero matches, Ted sneaks information out of the matchmaker's computer to visit an engaged dermatologist in an effort to debunk the prediction that there are no women out there for him. Meanwhile, Marshall and Lily become obsessed with chasing a strange and unusual critter out of their apartment.
When Lily decides to formally move into Marshall and Ted's apartment, Barney warns a skeptical Ted that the couple will eventually force him out. When Ted discovers that Lily replaced his beloved, but beat-up, coffee pot with a brand new one, he begins to think that Barney is right. Meanwhile, Barney invents a new dating law and tries to convince others to use it.
Marshall and Lily visit the former's family in Minnesota for Thanksgiving, but Lily feels out of place with the large, loud, and rambunctious family. Meanwhile, Robin and Ted are surprised to find Barney as the Volunteer of the Year at a local soup kitchen. Ted is even more surprised as he begins to uncover unethical acts taking place behind the scenes of the charity.
After Ted passes out after an especially wild night in town, he wakes up the next morning with a sprained ankle, a burnt jacket, a girl in his bed, and a pineapple in his room. Unable to recall everything that transpired over the course of the evening, he asks his friends and the girl in his bed, Trudy, to fill him in on the night's misadventures.
For New Year's Eve, Ted surprises his friends by hiring a limo to take them on an excursion through New York City's nightlife. Robin brings her new boyfriend, and the rest of the group each has a favored party that they each want to attend before the night is over. As the night progresses, the group picks up and loses people as the limo travels through the city. As the clock ticks closer to midnight, the limo gets stuck in traffic on the way to the last party.
Ted's decision to bring Robin as his date to a friend's wedding leads to an argument between the bride and the groom that abruptly ends the wedding. Ted and Marshall comfort the bride and groom and urge them to resume the wedding. They agree, but a last-minute opportunity at work leads Robin to unexpectedly cancel, leaving Ted to go alone.
Ted finds himself attracted to a mysterious woman whom he meets at the wedding. Unable to find her the next morning, Ted enlists the help of Barney in an effort to track her down. Meanwhile, Robin reveals that she left work early and saw Ted and the mysterious girl together the previous night, and has to confront her own feelings for Ted.
After initially agreeing to take things slowly, Ted and Victoria abruptly change course when they discover that Victoria will be out of town for their one-month anniversary. As they experience a series of milestones, Marshall and Lily wonder if their long relationship is out of milestones. Meanwhile, Robin decides to be Barney's "bro" for a guy's night out together.
When Lily chances upon Barney's first girlfriend, Shannon, the gang all relive their most embarrassing moments in order to persuade Barney to finish talking about his first relationship. Back when Barney was dating Shannon, he was a devoted boyfriend. However, when Shannon fabricated a story in order to leave Barney for a wealthier, better-dressed man, Barney was devastated. After a short period of sulking, Barney reinvented himself and his outlook on life to become who he is today.
Just as things are going well between Ted and Victoria, the latter is offered a surprising but incredible opportunity to be a fellow at a culinary institute in Germany. Lily invites Robin and Victoria to go wedding dress shopping with her, with some poor results after Lily destroys a $8,000 wedding dress. Marshall gets an interview for an internship with Barney's firm, and accepts an offer from Barney to get a friends and family discount from his suit tailor. After Marshall discovers the bill, a
Marshall and Lily have an argument over Marshall's new job at Barney's firm, which Lily alleges is having a negative effect on his values. Meanwhile, Ted feels guilty for not sending Victoria as many care packages as she has, and asks Robin for advice on maintaining his long-distance relationship. That evening, as Ted worries that Victoria is going to break up with him, he receives a call from Robin, asking to hang out.
When Ted receives an ominous message from Victoria asking saying she wants "to talk", Ted becomes convinced that he is about to be dumped. That evening, Robin invites Ted to her flat to hang out. Lily and Marshall try to dissuade Ted from going, but inadvertently give him more reason to go. Meanwhile, Barney tries to persuade Lily and Marshall to join him in a "legendary night out".
Robin invites the group to an awards banquet in which she is being honored for her newscasts. At the banquet, Barney convinces Ted that his date is actually a prostitute that he hired, while Ted also struggles with seeing Robin with her co-worker.
When Lily and Marshall's dream wedding venue has a sudden opening two months earlier than their planned wedding date, the couple scramble to decide on wedding arrangements. In order to preview a band that they are considering hiring, the group sneak into a high school prom where the band is performing. As they dance to the band, Ted and Robin decide to try to repair their friendship.
The matchmaking service finally returns with a match for Ted, but he puts his date with his "perfect woman" on hold as he decides whether or not he still has feelings for Robin. At the office, Barney enlists Marshall's help to prank a man who works in the building across the street. Meanwhile, Lily applies for an art fellowship in San Francisco without telling Marshall, even though it could ruin their wedding plans.
Ted ultimately decides that he wants to pursue Robin instead of the woman at the matchmaking service, and ultimately tries to win her heart by going to great lengths to romance her. Meanwhile, Marshall worries about his relationship with Lily when he learns of her acceptance to the art fellowship in San Francisco. As Ted tries to learn a rain dance in order to impress Robin, Marshall discovers that Lily left him for the fellowship.