The episode begins and the men are hanging out together. Ted has received a message from the Captain, on his answering machine. The Captain wants Ted to call him back at his “earliest convenience”. Ted for some reason is terrified on hearing this. The old Ted reminds his kids about who the Captain is. Ted feels that the Captain is sounding pissed. He tells Barney and Marshall he knows why the Captain is pissed. He then begins a story from a year and a half ago when the last time he met the captain. Ted mentions how he had broken up with Zoe at that point and was seeing a girl named Becky.
Lily had invited him to a gallery opening, which is where he ran into the Captain. The Captain is really curt with Ted but Ted understands, after all he slept with his ex-wife. Ted feels the Captain is being really rude and concludes that, “someone needs to bring him down a peg”. While Lily and Robin are busy making small talk with the Captain’s art consultant named Shelly, the Captain signals to Ted that he is going to kill him. He invites Ted, Lily and Robin to his apartment to see a new painting he has acquired. “It’s gonna blow you away” he says, looking threateningly towards Ted.
At his apartment, the Captain points a harpoon gun at Ted. Ted calms him down by saying, nothing happened between him and Zoe until she parted ways with him (Captain). The Captain tells Ted he isn’t mad at him anymore, because he has fallen in love with someone else. “So we’re fine” he tells Ted. “Just don’t steal this one from me too…ok” the Captain says jokingly. But, this got Ted thinking and he was really curious as to who this new lady in the Captain’s life was. Then before leaving the Captain’s apartment he sees Becky’s photo on the Captain’s desk and realizes who the new love of the Captain’s life is. Back in the present, Ted gets a call from the Captain and receives it. “What’s your friend Robin’s number” the Captain asks him.
Ted puts the Captain on hold and discusses the Captain’s request with the guys. In the end the guys give the Captain Robin’s number, because Barney is sure Robin wouldn’t mind. But, it turns out Robin does mind. She yells at the guys for giving the Captain her number. Robin then begins recounting her version of what happened when they met the Captain at the art gallery opening. In Robin’s version, the Captain isn’t being rude to Ted. In fact, Ted is so terrified on seeing him that he is only helping Ted complete his sentences. She then mentions that the Captain wasn’t glaring at Ted, as a matter of fact he couldn’t take his eyes off her.
She remembers how the Captain was making her feel really uncomfortable by aggressively flirting with her. In her version the Captain did not point a harpoon gun at Ted, but was instead pointing a remote at the TV behind him. He wanted to record a few shows and was setting the schedule on his TiVo. The Captain says he is not mad at Ted and mentions he is in love with somebody else now and while he is saying this he looks towards Robin. He invited her to see a painting in his bedroom and came onto her. She told him he is coming off a rebound and needs to cool off. She had told him to call her in a year and a half, which is probably why he has now called.
Marshall feels Robin needs to call up the Captain and let him down easy, so he can move on with his life. Robin calls the Captain and says she is engaged to be married. But, she discovers that the Captain is actually interested in talking to Lily and wants her phone number. Marshall feels Lily won’t mind her number being given. But it turns out Lily minds. Lily comes home and begins recounting her version of what happened when last time they saw the Captain and it’s possibly the correct version. According to this version it was Robin who began flirting with the Captain. Robin admits that’s the fact. Also, the photo on the Captain’s desk in his apartment was actually the picture of his boat and not Becky.
Lily did not like the painting in the Captain’s apartment and told him that. The Captain did not take too kindly to her criticism and insulted her by saying she was just a kindergarten teacher. To teach him a lesson Lily stole an expensive ashtray from his apartment. Marshall isn’t happy to hear this and asks everyone to leave so he and Lily can fight. Lily breaks down and admits to Marshall that the Captain was probably right and she is just a kindergarten teacher and nothing more. She is frustrated because she has a degree in art, but feels it’s too late for her to do anything with it. Marshall convinces her to follow her dreams. He tells her to quit her job as a kindergarten teacher to follow her passion.
Next day, Lily returns the ashtray and he isn’t mad that she stole it. He takes her to his bedroom and shows her that he has put the painting on the wall that she had liked. Turns out, the painting is fetching him $4 million. He feels Lily has an eye for art and hires her as his art consultant. Later, Lily tells the gang about it and they are overjoyed. The episode ends at this point.