- Ted reconnects with an old flame and soon remembers why he dumped her in the first place. Barney pays Robin to say outrageous things on the air.
- 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.—SSSS
- Ted finding a six year old shirt in his closet that he never liked but now loves makes him think that the same may apply to women. As such, he is contemplating starting up with one of his old girlfriends. Picking which one is the question. After discussing it with his friends, they decide on Natalie, who Ted dated three years ago. He broke up with her because he wasn't ready for a commitment yet. A problem is that Natalie doesn't want to even speak to him because of the way and when he broke up with her. Ted is able to overcome Natalie's anger and they do start dating again. But Ted inadvertently feels a sense of three year old déjà vu. Meanwhile, Barney dares Robin to say some crazy words on her on-air reports. In the reaction to Robin's reports, Robin comes to a sad realization about her professional life.—Huggo
- Ted (Josh Radnor) finds an old shirt that he used to love and decides to try again with a girl that he once dated. Robin (Cobie Smulders) decides to make some money on the side by putting on a different show for her viewership at Metro News One, by saying whatever Barney (Neil Patrick Harris) tells her to.—Death Becomes Her
- Ted (Josh Radnor) discovers he suddenly loves a shirt he owned for six years but had never previously liked. He meets everyone else at the bar, and discovers that he likes bourbon, which he thought he hated. Realizing that his tastes have changed, he decides to reconsider girls he has previously dated but did not seem right at the time. The gang help him think back to some of the women he dated (Steph who did 175 adult films for a month as she was broke, Jackie who hit a hitchhiker while driving when she was 16 & kept on driving), and he fondly remembers the times he had with Natalie (Anne Dudek), with whom he broke up because he hadn't been looking for a serious relationship at the time. Unfortunately, she angrily hangs up the phone when he calls. Lily (Alyson Hannigan) asks Ted about why Natalie would be so upset with him, and he admits that he broke up with her on her birthday, and did so by leaving a message on her answering machine. Ted then visits Natalie's apartment, apologizing for his past behavior and offering a giant sock monkey toy as a belated birthday gift. Ted begs her to give him another chance, even just a cup of coffee. They soon end up in bed together.
Ted and Natalie start dating again, and after three weeks things appear to be going well. His friends like Natalie and agree she is the best girl he has dated in years. Abruptly, Ted says he has to break up with her, because he realizes she isn't "the one". The guys come up with cliches to help him break up with Natalie, but Lily tells Ted to tell her the truth. The next night Ted takes Natalie out to dinner to break up with her face to face. She tells him it is her birthday but there is no need for a present since he has already given her the best present: she "can trust again". When she says her mother can't wait to meet him, Ted cannot wait any longer and tells her he wants to break up. Natalie is furious and Ted's attempts to be honest only make her angrier. She demands a good explanation, and when Ted can't give her a satisfactory response, she uses what she learned in Krav Maga (a form of Israeli army developed guerrilla street fighting) class to beat Ted up. Ted returns to the bar in pain and with the shirt that started it all torn, and decides that there really is no good way to break up with someone. Future Ted tells his kids that as a result, all of his happy memories of Natalie were replaced with the memory of her beating him up. He later states that Natalie eventually found a better guy, got married a year later, and raised three children. However, Ted's son mocks him for being beaten up by a girl.
Barney dares Robin (Cobie Smulders) to say or do increasingly unprofessional things ($50 for saying the word "booger", $100 for saying "nipple") on the news for money. She refuses at first, but performs the dares as she feels insulted by the seemingly unimportant stories she's assigned to cover and realizes that no one, not even her boss, watches her show. He assigns her a story to cover a hot dog stand next to city hall and Robin says the word "nipple". For $200, she says "I am a dirty dirt girl" and spanks her ass, while covering the death of New York's oldest twins. Next she honks her own boobs for the 3rd dare. After three dares, Robin is challenged to do the "Ickey Shuffle" at her next news report for $1000. Barney has the bar turn on the television to Robin's news show and tells everyone to watch for something amazing. Robin plans to carry out the bet, but changes her mind at the last minute. While interviewing New York City's oldest Hansom cab driver she realizes her job is important to the people she is interviewing even if no one is watching. She stands up but accidentally slips and falls into a pile of horse droppings and curses on live television. Robin is embarrassed, especially when Ted reveals that he too saw the incident on the internet.
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