Older Ted – "Now kids, when Aunt Robin was a teenager, she was, well, a Canadian pop star. But by 2008, she was an entirely different person. Which made the events of that week all the more surprising." Everyone is at the bar and they begin talking about Robin's breasts. She dressed up to meet an old friend, Simon, who happened to be her first boyfriend. They heckle her about her relationship with Simon. Older Ted – "This went on for a really long time. Some of the jokes were elegant and well crafted…others were crude, and ill-formed…and others were obvious, but needed to be said." They all run out of jokes for her and Robin continues to explain that they only dated for a week and a half, which in Canada is the whole summer. Robin tells the story of when Simon's band was finished playing a gig and Robin was helping him get packed up and he tells her that he is getting back together with Louise Marsh because she got a pool. Lily suggests that she wants to win the break-up and they figure out who won the break-up and come out with Robin winning, but that all changes when she sees him walk into the bar. Older Ted – "And sure enough, there was a clear winner and a clear loser. It just wasn't clear to everybody." Simon is now balding and pudgy, but Robin still thinks that he is awesome. At the apartment, they recap what happened at the bar when Simon joins them at the booth. Robin tells them that she still thinks that he has "it" and when the gang tries to talk up Robin and tell Simon that she is better than he is, she continually downplays herself. When Simon mentions that his band, "The Foreskins" is still together, she swoons even more. Simon and Robin met while they were shooting another video for Robin Sparkles. This prompts Ted to get up and search for the video. At the apartment, he decides that he will not stop until he finds the tape of her other video. Robin feels stupid about being so different when she is around Simon and Marshall suggests that it is revertigo and Lily has a bad case of it when she gets together with Michelle. Barney pipes up and tells them that she sounds hot and Marshall decides to mention Michelle's name and show Barney what happens. Lily goes into her room to call Michelle, but Barney doesn't immediately find out what happens between the two of them, but he does know that Marshall tells him that it is comparable to the two of them making out. Robin is upset that she didn't get a second chance with Simon, but later on that night, she meets everyone at the bar and tells them that Simon stopped by her apartment. Simon tells Robin that he made a big mistake and then asks her out. Robin agrees, which makes everyone upset. Michelle shows up and Michelle is African-American and she starts talking like she is from the ghetto. Barney makes it his personal goal to get with Michelle. Robin is hanging out with Simon and he asks her to play his demo on the news. She does and plays "Murder Train", one of their songs, when pictures of little puppies are on the screen. Marshall tells Robin that her revertigo is out of control. Lily asks what revertigo is and she tells them that she thinks that Ted and Punchy get together. Ted refuses to believe it, but then he remembers the last time that they got together and they play fought. Robin tells them that she likes Simon, but Lily says that they are worried about her and then they all start acting like Marshall and Lily are the parents and Robin is their little girl and they are chastising her. Robin tells them that she is going with Simon and will have sex with him. After Simon's gig, she gets his stuff packed back into his van, eerily like when she was 16. Simon breaks with her again for Louise Marsh.
Robin is talking to the rest of the group and Michelle has joined them. When Lily walks off, they talk to Michelle about why they act like that around each other and then she explains that she is getting her Ph.D. in behavioral psychology and there is an actual term for what happens with her and Lily, it is associative regression. Lily turns on a rap song and Michelle instantly transforms and starts to dance with Lily. Older Ted – "One by one, we all had to go home. Soon, it was just Robin." Barney returns to the bar and tells Robin that he has looked everywhere for her video, but he finds her crying because Simon dumped her again. He comforts her and she just cries and tells him that she thought that she wanted to feel that way again. Barney tells her that she was totally lame at 16, but now she is awesome, but not the first, the second most awesome. The first most awesome is his reflection in the mirror. Robin asks him to come back to her place and then whispers in his ear. They sit on her couch when they get to her apartment and they watch the other video, named "Sandcastles in the Sand." Barney is so excited about the video and it is what he expected. Robin finally admits that she was lame. Older Ted – "And so they watched it again. And again. And again. They watched it over and over that night, until finally, they stopped watching." Robin and Barney kiss.