When Ted's best friend Marshall proposes to his girlfriend, Lily, Ted realizes he'd better get a move on if he hopes to find true love. Ted soon meets Robin in a neighborhood bar, immediately becomes smitten and scores a first date. But when Ted can hardly wait to see her again, his eagerness threatens to scare her away.

In a desperate attempt for a second date, Ted invites Robin to a party he is throwing. However, she doesn’t show up and he keeps throwing parties in the hopes she will finally arrive.

Ted agrees to let Barney spice up his love life, and ends up on a crazy adventure of flying to Philadelphia, encountering the law and visiting the Liberty Bell.

Ted's outlook on his continuing search for love is altered when he rediscovers a shirt that has not seen daylight in years. Meanwhile, Barney amuses himself by coaxing Robin into sacrificing her job by saying completely outlandish things on air live for a cash reward.

Ted and Barney start checking out the club scene with their friend Robin, whereas Lily and Marshall try to participate in some more grown-up activities, as they draw slowly nearer to their wedding.

Ted makes his yearly pilgrimage to the rooftop Halloween party in search of a girl dressed as a pumpkin who he met years ago. Meanwhile, Robin is dumped after driving her new boyfriend away with her independent ways.

When Ted turns to a matchmaker to find love, he is sent away matchless. When a matchmaker with a 100 percent success rate turns Ted away because he is not compatible with any of the available women in her database, he is still determined that he is going to find his match. After getting information from the matchmakera 's computer on the sly, Ted pays a visit to a very cute, but very taken, dermatologist in an effort to debunk the prediction that there are no women out there for him. Meanwhile, Marshall and Lily are obsessed with ridding their apartment of an unsightly critter.

As Lily becomes more of a permanent fixture in Ted and Marshall's apartment, Ted feels like he is being edged out of the mix by his engaged roomies. Petrified of being left alone and homeless, Ted tells Marshall that when he and Lily are married, he wants the apartment. The problem is that Marshall wants to keep the place too, so they settle it like real grown-ups--launching into a sword fight that leaves one man down for the count.

When Ted and Robin decide to help feed the homeless on Thanksgiving Day, they are in a state of disbelief when they run into Barney and discover that he is a regular volunteer at the homeless shelter. Thanksgiving doesn’t end there for the trio, for they end up somewhere that only the real Barney would bring anyone to for a holiday meal. Meanwhile, things do not go very smoothly when Marshall and Lily pay a holiday visit to Marshall’s family in Minnesota.

After Ted overdoes it during a night out on the town, his friends help him to put together the pieces of his antics the next morning. With the encouragement of his friends, Ted decides to let his hair down for a change and ends up having a fun and adventure-filled evening. However, now the problem is that he can't quite recall everything that transpired over the course of the evening and now he must rely on his friends to fill him in on the night's misadventures.

Ted surprises his friends with a styling and well-planned out New Year’s Eve excursion around the Big Apple. After spending New Year’s Eve apart from his friends last year, Ted is dead-set on ringing in this new year with his best pals at his side and doing it in style. As Lily, Marshall, Barney and Robin are chauffeured around town in a limo hired by Ted, the night takes some interesting twists and turns -- and when the clock strikes twelve, Ted may end up getting that kiss he has been longing for or at least the promise of something good to come.

Ted is planning to bring Robin as his date to a wedding but the bride says he did not RSVP with a guest. When he goes around her and gets permission from the groom, a man named Stuart. Ted’s fantasy with Robin is in trouble unless he finds a way to get them back together.

At a wedding, there's instant attraction between Ted and a woman. Both agree to preserve the evening in memory by not exchanging names or numbers, but Ted falls too hard to let it go and tries to find out her identity.

After agreeing to take things slowly and not have sex for a month, Ted and Victoria decide that they have waited long enough. With Marshall and Lily out of town, the timing seems perfect. However, when the two change their plans and decide to stay home, they end up hiding in the bathroom in an effort to avoid ruining the moment for Ted. Meanwhile, Robin replaces Ted as Barneya 's wingman for a boya 's night out.

As Barney shares his most embarrassing moment with the gang we see flashbacks of what he was like before he started wearing suits all the time and sleeping around, and learn what caused him to change.

Just as things are going so well with Ted and Victoria's relationship, Victoria gets her dream offer and the couple is confronted with some hard decisions about their future. Meanwhile, when Lily ruins a very expensive wedding dress and Barney talks Marshall into buying a very pricey suit, Marshall is forced to interview at Barney's company and give up his dream of working for an environmental law firm in order to earn more money.

After a rough start on the new job at Barney's company, Marshall conforms in order to be accepted by his crude and obnoxious frat boy co-workers. However, he soon realizes that staying true to himself and his relationship with Lily is what is truly important. Meanwhile, Ted is convinced that Victoria is going to dump him after receiving a let's talk e-mail, so when the phone rings and it is Robin inviting him over late night, Ted must decide between going to Robin's place or waiting for Victoria's call.

Convinced Victoria is about to dump him, Ted accepts a late night invite to Robin’s place. When Robin inquires about his relationship with Victoria, Ted tells her that they broke up. As things start to get hot and heavy between them, Ted’s lies are eventually exposed and his theory nothing good happens after 2 AM proves to be true. Meanwhile, Barney tries to convince Marshall and Lily that the best things actually do happen after 2 AM

Everyone is invited to a banquet when Robin is nominated for a news award, and Barney sets Ted up with a hot date.

Lily and Marshall's wedding date has just been pushed up, and in order to hear a potential band for the big wedding, Lily crashes a high school prom.

When Lily’s car breaks down on the way to a secret appointment, Ted changes a very important date to come to Lily’s rescue. However, Lily drives off after confidentially telling him that she is on her way to an interview for a summer arts program that would derail her wedding. Despite Ted’s input, Lily decides that she must go through with the interview or she will always wonder what could have been. After several months, the matchmakers finally comes through with a match for Ted.

In an attempt to capture Robin's heart, Ted declares his love to her. Once again, Robin resists and prepares for a weekend away with her co-anchor, Sandy. Ted makes one last romantic gesture which leaves their fate as a couple in Robin's hands. Meanwhile, when Marshall finds out about Lily interviewing for a summer program, a heated fight ensues.