- Ted goes on a boating trip with Zoey's husband, "The Captain." Meanwhile, Barney's "Mermaid Theory" prevents Marshal from having a nice dinner with Robin, and the narrator tries to recall the details of a fight between Lily and Barney.
- Since no one else in the group can make it, Zoey and Ted are going out to a function by themselves. Lily sees this "date" as dangerous territory for the two of them since Zoey is a married woman, and they all think Zoey's husband, George van Smoot who Zoey and by association the gang call "The Captain", has a sinister air about him. It becomes even more awkward for Ted when Zoey lies to the Captain, she telling him that she is out with "friends" plural. Lily believes the only way for Ted's friendship with Zoey to continue is if he includes the Captain in their outings. But when Zoey can't make the planned outing - a sailing trip - Ted is afraid for his life having to spend 6 long hours alone with the Captain in open water. Meanwhile, Robin and Marshall, who realize they never spend time alone together, decide to go out to dinner without the others. Their evening could not be more awkward, which they both realize. Marshall attributes the awkwardness and the two of them never spending time alone together based on something Barney calls "the mermaid theory". And Lily and Barney get into an argument over something that Lily says to Barney... or so Ted in 2030 remembers not so correctly.—Huggo
- Marshall and Robin realize they've never really spent much time alone and decide to go out to dinner together. The dinner turns out be awkward, to which they agree it's because they don't spend much time together outside of the group. Marshall then explains Barney's "Mermaid Theory": Long ago, sailors used to picture manatees as mermaids due to long periods without female contact (the vision is shown with Barney and Marshall as sailors). After hiring an unappealing female assistant two years ago, Barney had told Marshall that though Marshall views her as a "manatee" now, as he spent more time with her, she would eventually become a "mermaid" in his eyes. Barney says the "mermaid clock" is ticking, and over a year later, his assistant does in fact seem like a mermaid to Marshall, much to his horror. Marshall tells Robin he doesn't want her to turn into a mermaid out of respect for Lily, though he explains a woman can go back to being a manatee by becoming pregnant. The two eventually have a good time by getting drunk, though when they return to the apartment, Marshall begins seeing Robin as a mermaid. When she throws up all over the floor, however, Marshall once again sees her as a manatee, much to his relief.
Soon after Marshall and Robin had agreed to hang out, Barney had asked Lily the same, who refused, offending Barney. However, Future Ted has trouble recalling what exactly the argument was, and only after explaining the mermaid theory does he remember the actual story. This event had in fact taken place farther in the future, while Lily was pregnant. Lily had refused because she thought Barney would picture her naked, though when Barney says he views her as a manatee now that she's pregnant, she becomes angry. Later, the two make up when Barney says Lily can become a mermaid again when she begins breastfeeding. Ted then walks in wearing a green dress, stating "Now we're even!" though Future Ted says that's a story for another time.
Future Ted explains Zoey has since become a normal acquaintance among the group, although Ted and the gang are secretly terrified of Zoey's husband, "the Captain". Ted tells the group Zoey has invited them to an art gala, though when only Ted expresses interest, Lily cautions Ted on hanging out with Zoey alone. Lily says that there are rules about hanging out with a married woman. Don't go anywhere near candles, no sharing food and no lying to the spouse about anything. Ted promises nothing will happen, though while the two are together, Zoey lies to her husband when he calls by saying she is "out with friends" instead of specifically mentioning Ted.
Zoey tells Ted not to worry about it, but when he tells Lily later, she becomes worried. Lily then says if Ted can become friendly with the Captain, it can straighten things out. Zoey invites Ted to come on their boat one evening, though it turns out to only be with the Captain. Due to the Captain's seemingly sinister undertones, Ted suspects the Captain knows he's been hanging out with Zoey and fears he will be murdered. While the Captain heads below deck to get something, Ted prepares to jump from the boat, but finds his fears were for nothing as the Captain returns with drinks. However, the boat hits a bump and Ted falls in the water. After being brought back on the boat, Ted admits his fears, though the Captain tells him he's glad Zoey has found a new friend and expresses his interest to be friends as well, to which Ted accepts. Ted later tells Zoey he really does think of the Captain as a nice guy, but hopes he and Zoey can continue to be friends. Ted decides they shouldn't hang out if either begins to develop feelings for the other; while both deny any such notion, a ticking clock is heard in the background, indicating the mermaid clock has begun.
In the end, the sailor story is extended, with sailor Marshall lamenting about not finding land yet. He then begins to envision Barney as a mermaid, to which he affirms they really need to find land.
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