- Kevin proposes to Robin, but will he take it back when Robin tells him she can't have children? Meanwhile, Barney and Ted try to score on the "drunk train" to Long Island, but something is surprisingly holding Barney back.
- Marshall and Lily and Robin and Kevin having been double dating. Robin and Kevin have had to endure watching Marshall and Lily fight all the time, while they say that they don't fight. Regardless, Kevin decides that he wants to move to the next step with Robin: he asks her to marry him. After thinking about the proposal, Robin thinks she knows how she will answer, but first she needs to clear the air which may change the picture entirely. Meanwhile, despite Barney having a sure thing, he acts as wing man for Ted. Quinn, the wing girl of Ted's prey for the evening, ends up being wise to Barney's manipulative ways. For missing out on his sure thing, Barney believes that Ted owes him one. What Barney wants as his payment, after hearing about it from Marshall and Lily, is for him and Ted to take the "drunk train" i.e. the last train out to Long Island where everyone inebriated is willing to go to bed with anyone else on board. The drunk train experience doesn't end up being what either expects, so they have to figure out why.—Huggo
- Because Ted asked him to be his wing-man, Barney meets a woman named Quinn (Becki Newton) who sees through all of his plays. Barney claims that he has Enormous Penis Syndrome and is organizing a 10K fun run to raise awareness about the problem and is a former surgeon general. Quinn says that she has the "I am not a gullible dumb-ass disorder". Quinn says that they are just there as backup for their friends and refuses to engage in any conversation with Barney. Quinn says that she knows Barney's type, who wears a sit all the time, and has a rule about everything, and he ends up most night alone at the strip club, while convincing himself that his life in Legendary.
To compensate for the poor night out the previous evening (for which Barney says Ted owes him 3 hours of his time), Barney insists that he and Ted try their luck on the late-night "Drunk Train", the last train out of the city to Long Island, which is filled with the drunkest, most desperate bridge and tunnel people who are desperate to hook-up with anything that moves. The duo runs into difficulty scoring on the train (they go to sleep as it was already too late), but they try again. The 2nd night the guys try hard but strike out at every attempt. They spend the night at Marshall and Lily's place in Long Island. They succeed on their third attempt when they find a solution (getting drunk themselves), until Barney reveals that he and Quinn had hooked up that first night. Ted realizes that Barney keeps thinking about Quinn and tells him that if he feels something for her, he should go after her, as it's Valentine's Day and such opportunities are rare. Ted admits that he's disappointed that he still has no-one he can't stop thinking about.
On a couples retreat in Vermont for Valentine's Day, Marshall and Lily try to show Robin and Kevin that the success to a long-term relationship is not to "keep score". Lily and Marshall eventually end up bickering over the issue. Like how they have to bring out all the tacky Minnesota gifts whenever Marshall's mother is coming to visit them. Or how Lily drags Marshall to the experimental theatre piece (many hours of just screaming). Or how Marshall killed Lily's cousin's dog. When they return home they decide, as impending parents, that they should work together as a team and no longer keep score. On the weekend trip Kevin proposes to Robin, who wants to accept but has to decide how to tell him that she can't have children and doesn't ever want them.
After consulting Marshall and Lily, she tells Kevin, who still wants to marry her. However, because Robin does not want Kevin to regret marrying her, she firmly tells him that she does not want to have children ever, not even by adoption, forcing Kevin to truly reflect on the issue. He then takes back the proposal and they break up.
When Ted and Robin meet on the roof, Robin explains everything to him and confesses that she finally feels ready to have a serious relationship but believes she won't be able to find someone who can accept her now. In response, Ted says that he could and tells her he loves her.
Meanwhile, unknown to Barney, Quinn is revealed to be a dancer at the Lusty Leopard strip club and comments that he should have recognized her earlier due to his frequent visits. Quinn is actually the stripper 'Karma' whom Barney knew.
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