It's the year 2030 and an older Ted Mosby is telling the story to his son and daughter about how he met and will eventually marry their mother. This is where we meet for the first time Ted, Lily Marshall, Barney and Robin.
After telling Robin that “He loves her”, things fall apart for she and Ted and he figures that it's all over for the two of them, but not for long as Ted finds out from Lily after she met Robin that she (Robin) likes him and Ted tries once again to win her affections, by throwing a party at his and Marshall's place, but it turns into 3 parties in 3 nights, when Robin was a no show for the first 2. Meanwhile, after Lily said yes to Marshall's marriage proposal, she has become extra affectionate to him in the bedroom and Marshall is worrying about finishing a huge paper…
Rather than go to McLaren's, their usual hangout, Barney convinces Ted to go to the airport with him to “pick someone up”. It turns out that they're there to pick up some girls. While doing this, they fly to Philadelphia, get arrested by airport security and that's when Ted starts to wonder why he ends up in these adventures with Barney. Meanwhile Marshall has studying to do, so Lily and Robin do a girls night out and Lily notices guys are buying drinks and try talking to Robin, so Lily starts to wonder what it would be like to have her engagement ring off, and with …
Ted dated a girl, Natalie, three years ago and quickly got annoyed by some of her antics. Therefore he broke up with her, leaving a message on her answering machine on her birthday. His blamed his behavior on his immaturity and after being forgiven by Natalie they end up getting back together. Robin meanwhile realizes that no one is interested in her show and plans to do or say crazy things which Barney dares her to.
Robin manages to get into OK, an ultra hip exclusive nightclub. Ted and Barney will be going with her, but not Marshall and Lily, as they have been doing a lot of “Classy grown-up things”, as she referred it to and thinks it may be time for she and Marshall to grow up and put behind the things they used to do back in college. While at the club, Robin runs into problems as she cannot get into the VIP Room, then while outside trying to get it straightened out,a different front door bouncer will not let her in, even though she is on their list to get in, but her name is …
On Halloween, Robin and her new boyfriend Mike meet for a Double Date with Lily and Marshall, who are eager to win the costume contest. Robin turns out as someone who is not so much into “couple things” so the dinner is not as pleasant as expected. Barney actually wants to take Ted with him to a Victoria Secret's Party, but Ted heads for a party on the roof of his apartment house, where he a few years ago met a beautiful woman, which is just called the “slutty pumpkin”. Eager to meet her again, because he never had the change to call her because he lost her number, he…
Barney takes Ted to matchmaker Ellen Pierce, but while Barney gets thrown out, Ellen promises to find a woman for Ted within three days. This promise has disastrous results: the woman that suits him the best has already a boyfriend. Lily and Marshall have problems with some sort of cockroach or mouse that is in the apartment and they cannot get rid of.
Lily moves in with Ted and Marshall and although it was Ted's idea to ask Lily to move in, he starts to worry that the apartment changes too much with Lily there. Another issue for Ted is who will keep the apartment after Lily and Marshall got married. In the end, a real fight starts between Ted and Marshall over the apartment.
It's Thanksgiving and while Lily and Marshall visit his family in Minnesota, Robin and Ted want to volunteer at a homeless shelter kitchen. Surprisingly, Robin and Ted meet Barney at the kitchen, who has been doing volunteer work for the past few years. At the kitchen, Ted meets Amanda, who seems to be a quite nice girl until everything turns out to be different. Lily has some issues with Marshall's family and is unsure about how her future with Marshall will look like.
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 …
It's New Year's Eve 2005 and Ted spends a large portion of his Christmas bonus for a limo for he and the gang. In addition, he has outlined a plan how they will ring in the New Year. Unfoirtunatley, things don't always go as planned.
Ted is searching for a date for a wedding. He asks Robin to come with him to the wedding as his “date” and she says yes. Problems evolve when the bride-to-be Claudia tells him he didn't check “plus one” on the reply card and forbids him to bring someone along to the wedding. Ted now has problems to tell Robin that she cannot come with him and asks the Stu, Claudia's future husband, if he can bring a “date” and he says “yes”. This leads to further problems.
Ted meets a beautiful woman named Victoria at Claudia's and Stu's wedding and they spend a great time together that night. Unfortunately, Ted and Victoria made a deal that they will never see each other again after that night and they do not exchange telephone numbers or anything else. The morning after the wedding party, Ted wants desperately to see the girl again. So he starts searching for her and asks anyone from the wedding who could have possibly know her, but she seems to be lost.
Ted and Victoria had decided to wait for one month before sleeping together, but Victoria forgets that she'll be out of town on that day. Meanwhile Marshall and Lily celebrate their nine year anniversary, and Barney and Robin have a bros night out.
During a game night Robin gets to meet Victoria. What actually was planned to be a funny night turns quite serious when Barney's former love Shannon gives an old tape to Lily which shows the “real” Barney. While watching the tape an embarrassed Barney storms off. When he returns, Barney tells a story from 1998, when he seems to have been a whole different person, and what made him the person he is today. To make Barney feel better, all others also tell their most embarrassing stories.
Victoria is about to leave to go to Germany for two years for a donate fellowship. Ted doesn't know if he should her ask to stay or if he should tell her to leave. Marshall needs a new suit and Barney helps him. Meanwhile, Robin and Victoria accompany Lily to a wedding dress fitting and also the girls talk about whether Victoria should leave Ted or not.
After a month of long-distance-relationship with Victoria, she's already sent Ted three care packages full of stuff he likes, but he hasn't sent her any. Marshall works in Barney's office and doesn't like it all or the people he works with, but Barney talks him once again into keeping the job. Marshall decides that it must be easier to work in the office if he adapts to the people he is working with and gets some “get psyched” training from Barney.
After having quite a rough day and being a little drunk, Robin calls Ted in the middle of the night and asks him if he wants to come over to her place. Ted, of course, says that he will come. On his way to Robin's apartment, Ted starts to ask himself if it is okay to go to Robin since he still has got his girlfriend Victoria and asks his friends for advice.
Robin invites everybody to a banquet and Ted is insecure about bringing a date or not. Barney offers to hook him up with a prostitute while Robin brings a real date. Ted pretends to be cool with the fact that Robin has moved on, but Robin's date is her sleazy colleague Sandy Rivers whom Ted and Marshall constantly make jokes about when watching him on TV. With all these people in the same room, the evening seems to be getting interesting.
Marshall and Lily finally have got the perfect place they always wanted to get married at. The only problematic thing about this is that the place is only available in two months. So, this means a lot of work for everybody. To listen to a band Marshall wants to play at the wedding, Lily,Barney and Robin sneak into a High School prom. While the other three are at the prom, Marshall and Ted, who had actually planned a “men's night”, are wrapping up wedding invitations until Lily wants Marshall to come to the prom too. Of course, Ted comes along too.
It's Ted's 28th birthday and he still keeps looking for the perfect girl. Apparantly he is about to find her since the matchmaker he once hired to find him a partner has finally found the perfect match. When he is about to meet her, Lily calls him because she is in trouble. Marshall gets himself into an office war between Barney and some guy named “Clark Butterfield” in which the guys do all kinds of gross things to each other.
Ted makes a final attempt to win Robin's heart. Marshall and Lily's relationship is in jeopardy.