- The gang struggles to quit smoking while Robin clashes with her new jaded co-worker.
- Although he vowed to Robin and Marshall that he would never tell them, Ted finally tells his kids that at one time both Robin and Marshall used to smoke. In 2009, they both felt like they had good reason to do so. Marshall, only an occasional smoker, always said that each cigarette was his last. But when his old boss, the meanest man nicknamed Artillery Arthur, became his new boss, he thought he was going to be fired - again. So when Marshall found out that Arthur was a smoker, Marshall used it as a bonding mechanism to keep his job. Robin, at the time anchoring the morning show, had just gotten a new co-anchor named Don Frank. Don was a career morning show host, moving from morning show to morning show across the country. Robin hated Don for what he represented: a person who had given up on his career, stating that they were on a nothing show that nobody watched. Deep down, Robin feared that he was right. So when she managed to get a scheduled on-air interview with then New York City Mayor Michael Bloomberg, he a staunch anti-smoker, she had just as good reason to quit. In telling these stories, Ted also lets slip the smoking histories of a few other people his kids know and love.—Huggo
- Future Ted explains how frustrated Robin got at her early morning news show, and describes her taking a smoke break up on the roof, much to the surprise of his listening children. She is then joined by Marshall, who is stressed about his new department head Arthur Hobbs (Bob Odenkirk). Arthur has been tasked to let people go from the legal department at GNB. Barney explains that Marshall's job is at risk because Arthur does not remember Marshall (Arthur is mad at everyone, its the ones he doesn't know are the ones he cuts loose), even though Marshall worked for him before and made an angry, explosive speech when he quit. When Marshall takes a rooftop break at work, he bumps into Arthur, and to gain his confidence, they share a smoke. Arthur now starts remembering Marshall's name.
Even though Marshall rigorously cleans himself, Lily can still smell the smoke on him, and uses it as an excuse to start smoking again herself (which leads to her voice lowering to a raspy growl). Finally, Ted and Barney feel left out as their friends smoke outside MacLaren's, and they join in as well. Barney only smokes in certain situations. Post coital, with Germans, coital, birthdays, to annoy his mom, pre-coital, on a sailboat, pregnancy scares. He is always pre-coital. As the week continues, their smoking takes its toll, decreasing Ted's stamina on the stairs, worsening Lily's voice, burning Barney's tie, and giving Marshall's boss, Arthur, a heart attack. They all pledge to stop smoking, though Robin is reluctant at first but agrees when Ted argues that the Mayor (whom she is trying to invite to her show) is an anti-smoking crusader.
Meanwhile, Robin is joined by a new co-anchor, Don Frank, a legend of the pre-6am television world, having broadcast in 38 media outlets. Robin is impressed at first, but is quickly disappointed by Don's lack of professionalism and total indifference to his job (he says "brain fart" on live TV)-to the point that he does the news in his underwear. She works even harder to prove that her job means something, even booking Mayor Bloomberg on the show. When Don tells her to stop taking her job so seriously (as he has even been on a network show with ergonomic chairs, dressing rooms, but was fired as he was going through a bitter divorce and reeked of gin), Robin loses her temper and calls Don a rude, unprofessional loser; in the middle of her tirade, Don tells her that the Mayor canceled. As Don lights up a cigarette (on live TV) and offers it to Robin (he says he is a loser, just like Robin said, but at least he has accepted it), saying she'll never quit smoking (just like she will never be a network anchor), the gang calls from the apartment, pleading for her not to break their pact. She agrees, but when she returns to the apartment, she finds everyone smoking on the roof. Future Ted tells the audience in the voice-over that Robin and Don were dating within three months.
The gang agrees to have "one last cigarette" as the sun rises, but Future Ted reveals it took years for each member of the gang to actually quit, listing events in their lives that lead to the change: Lily quits the day she decides to try to get pregnant; Marshall quits the day his son is born; Robin quits in June 2013; Barney quits in March 2017; and Ted quits two weeks into dating the children's mother.
Throughout the episode, Marshall says he had his first cigarette when he was 13, and is shown periodically imagining himself traveling back in time and beating up his younger self for taking up the habit in the first place. At the end of the episode, Marshall once again visits his 13-year-old counterpart in 1991, but instead of beating him up, he apologizes and gives him a peace offering: a picture of Lily, to which Young Marshall replies "Wow she's hot". Marshall explains to his younger self that he will one day marry her. Surprised and excited, Young Marshall disappears into his tent with the picture to apparently masturbate; Present Marshall is disgusted at first, but then understands and walks away.
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