- When Ted receives an unexpected call from The Captain, the gang reminisced about their last awkward encounter with him.
- A nervous Ted receives an unexpected telephone message from The Captain, his old girlfriend Zoey's wealthy ex-husband. Ted believes The Captain called to exact his revenge against him, thus he tries to avoid The Captain's follow-up call. Ted, Robin and Lily reminisce about the last time they saw The Captain a year and a half ago at an art gallery, but each remembers the evening slightly differently. As they piece together their three stories, in there may lie the real reason The Captain got back in touch with Ted, and why that evening affected one of the three so deeply. Meanwhile, Barney, who was not there that evening, tries to infiltrate himself into Ted, Robin and Lily's individual stories, while Marshall wants Ted to reconnect with The Captain on the minute possibility that Marshall will get to sail on The Captain's boat.—Huggo
- When Zoey's (Jennifer Morrison) ex-husband, The Captain (Kyle MacLachlan), unexpectedly calls Ted, the gang reminisces about what happened when they last saw him a year and a half earlier. Ted tells Barney and Marshall that he, Robin, and Lily had attended a gallery opening a year and a half ago, after Ted and Zoey had broken up and he was dating Becky (Laura Bell Bundy). The Captain and his art consultant Shelly (Eva Amurri) showed up at the gallery; Ted recalled the Captain looked tense but had invited them all to view a painting at his apartment. After he threatened Ted with a harpoon gun, Ted claims that the Captain mentioned he had moved on. However, Ted screamed upon seeing that the Captain had a picture of Becky. This terrified Ted as he knew that the Captain would blame him for stealing Becky from him too.
When Ted calls the Captain, the Captain asks for Robin's number. Robin tells the guys her part of the story. Ted had been high (on a 'Sandwich' he shared with Becky) and the Captain was hitting on her, making her feel uncomfortable. The harpoon was actually a remote control. At the Captain's apartment, she walked into his bedroom and saw the Captain lying on the bed in a seductive manner. According to Robin, she turned him down, telling him to pull himself together and call her in a year and a half. On the advice of the guys, she calls the Captain and tells him she's engaged. The Captain reveals that he is actually looking for Lily and had gotten her mixed up with Robin.
Lily tells the gang that Robin had been severely drunk at the gallery opening (the result of a long meeting at work followed by several shots at the bar) and as a result, was flirting with the Captain. Lily complimented an elephant painting, making the art consultant very uncomfortable. When the Captain showed Lily the masterpiece he had acquired in the bedroom, Lily felt that the elephant painting would look better in the room. He dismissed her opinion because she was a kindergarten teacher; Lily took those words to heart, and in retaliation, stole his ashtray. The picture on Captain's desk was not of Becky, but simply a yacht that he admired.
Marshall and Lily argue (having asked the others to leave after telling Lily's side of the story), causing Lily to admit that she isn't returning the ashtray because a "kindergarten teacher" is all she is. After months of keeping, it from him, she finally admits her regrets about not using her art degree and instead becoming a mother. Though Marshall reassures her that she will be able to pursue her art career again someday, Lily worries that there is a certain point where this stops being true.
Meanwhile, Barney repeatedly attempts to insert himself into Ted, Robin, and Lily's story. When his friends become fed up with him, he reveals that while everyone else has something they are passionate about, Barney feels the only thing that makes him stand out is being involved in crazy stories. Ted and Robin invent a part of the story where Barney seduces the Captain's art consultant using a play from "The Playbook" so Barney is included.
The next morning, Lily meets the Captain at his apartment to return the ashtray and finds out why he needed to see her - after that gallery opening, he bought the elephant painting and hung it in his bedroom, finally agreeing that it was a nice touch. He is now selling it for $4,000,000, after the artist had become a star in the last year and a half. To make it up to Lily for his harsh words to her, he offers Lily a job as his new art consultant. When Lily asks what happened to his old art consultant, the Captain mentions that she left the party early that night after meeting a royal archduke at the gallery (with the tag showing Barney seducing the consultant at the gallery using "The Royal Archduke of Grand Fenwick" play he made-up when Ted and Robin inserted him into the story). The episode concludes with the gang celebrating Lily's new job.
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