Ted suddenly finds a shirt he has not worn in forever, and finds that he likes it, even though before that day he had never considered wearing it. He meets everyone else down at the bar, and finds that he also suddenly likes Bourbon, which he had hated before. He suddenly decides that maybe he should start considering girls he has previously dated; Barney objects to this idea, saying that the only reason to date a girl who one has previously dated is if she received breast implants. Ted ignores Barney's advice and decides to re-date Natalie. Initially Ted isn't sure if she would remember him, but it turns out she hasn't forgotten Ted. When Lily confronts Ted about why Natalie would hang up on Ted so rudely, Ted reveals that he broke up with her on her birthday by leaving a message on her answering machine (Natalie also reveals that this happened as her friends were waiting to give her a surprise party). Lily begins slapping him, saying that he shouldn't have broken up with her on her birthday, or broken up with her over the phone. The guys all point out that there is no good way to break up with a girl. Ted then visits Natalie's apartment, apologizing for his past behavior, and begging for a second chance, with the help of a sock monkey. She decides to give him a second chance, and things appear to be going well. However, despite how much everyone else likes her, Ted feels that she isn't the one, and has to break up with her. However, Lily encourages him to do it the right way and be honest, and he takes her advice. However, at dinner right before he is about to break up with her, she tells him it is her birthday, and when he breaks up with her again, she demands a good explanation, and when Ted can't give her a satisfactory response, she uses what she learned in a Krav Maga class to beat Ted up. Ted returns to the bar in pain and with the shirt that started it all ripped, and decides that there really is no good way to break up with someone. Along with this life lesson, what Ted's son also learns from his father's story is that his father was beat up by a girl.
Meanwhile, Barney dares Robin to say or do things on the news that are questionable for money. Robin refuses at first, but performs Barney's first dare when a Freudian slip causes her to say the word "nipple" when she meant to say the word "nickel." She then does the second dare, saying "I'm a dirty, dirty girl," at the end of a news story and spanking herself. When she finds out that no one, not even her boss, watches the news channel she reports for, she decides that she might as well perform the dares. On her third dare from Barney, she honks her own breasts during a report. Barney, as the fourth dare, wants Robin to do the "Ickey Shuffle" at the end of a report in tribute to Ickey Woods, a famous football player for the Cincinnati Bengals. She plans to do this, but then realizes the importance of her job while interviewing New York City's oldest Hansom cab driver. Even though she does not mean to do this, she steps out of the buggy and falls into a pile of horse droppings, which surprises even Barney. Even though no one had known about the previous dares Robin performed, Barney had the TV tuned to her news channel in the bar. Thus everyone in the bar at the time saw her fall off the buggy. Robin is very embarrassed, especially when Ted reveals that he saw it on the internet.