- After Robin finds out her mother isn't coming to the wedding, the group recalls a fateful night six months ago when Barney accepted the "challenge" of a lifetime, and Ted made a decision about his pursuit of Robin.
- Usually cold-hearted Robin is in tears over the news that her mother will not be attending the wedding. In trying to make Robin feel better, Ted, Barney and Lily each are brought back in their memory to a time six months earlier. Then, Lily noticed that the challenges that Barney always accepted in picking up women were those that he issued for himself. So Lily and Robin went on a quest to issue Barney challenges on picking up women that they believed he could not complete. This quest became an all night task. The one challenge that Barney felt like no challenge at all ended up being the most difficult not so much for the challenge itself, but for the advice he got in return. What Robin, Barney and Lily are and were unaware of is that at that same time, Marshall tried to convince Ted that, based on inside information, he should still try to pursue Robin, despite Ted vowing that their relationship was then purely platonic. Events, including a telephone call from Chicago, made Ted truly reevaluate if indeed there was a future for him and Robin.—Huggo
- At 11am on Saturday, with 31 hours left before the wedding, Barney, Ted, and Lily comfort Robin over the news that her own mother is not attending her wedding. Barney takes this as a challenge to cheer her up, but Lily claims Barney never finished a challenge to pick up diapers and samosas in the fall of 2012. Barney recounts the story.
One night at the bar, Barney discussed with the gang the fact that the group's only true male/female platonic relationship was between Marshall and Robin (with a fantasy showing that Marshall wouldn't make out with Robin even if their and Lily's lives were at stake). Barney says that a relationship is platonic if there is genuinely no chance of a hookup within the next 20 minutes. By this point, Lily had been fed up with Barney's own creative plays to pick up women. She dares him to take up challenges that she and Robin will choose - which include getting a woman's number while speaking like a dolphin, wearing a garbage bag and not using any word that has the letter E. Robin approaches a redhead at the bar and tells her that Ryan Gosling is interested in her and will come by to meet her and she has to keep men away from her till that time. Robin challenges Barney to pick up the redhead. Barney guesses that the redhead is waiting for someone and going by her facial clues, he eventually figures out that she is waiting for Ryan Gosling. Barney pretends to be Ryan who had to get a plastic surgery to play to a man much more handsome than himself. Barney gets her number.
Seeing that Barney has passed all their challenges, Lily and Robin decide to make him do an errand for them by inserting the challenge of picking up a woman while performing the request - to buy her a pack of diapers for Marvin and samosas for Robin. Barney buys the items and then attempts a play on a woman at a pharmacy; the woman is actually Ted's future wife, who sees through his facade and calls him on it (with Future Ted telling his kids this was "How Barney met your Mother"). Outside, the two talk about Barney's failed relationship with Robin and how he had felt lost since they broke up. When Barney says he can easily woo back Robin, the woman declares that if he really wants her so much, he will have to give it his very best shot. The woman leaves him and Barney returns home, leaving behind the diapers and samosas, to draft "The Robin."
Elsewhere, Marshall and Ted watch a game between the Washington Generals and the Harlem Globetrotters. As they watch the game (with both supporting the Generals), the two begin talking about Ted's feelings for Robin and whether he will not pursue her again. Ted assures Marshall he isn't interested, as he knows Robin isn't interested in any real commitment, so their relationship is just 'platonic'. Marshall tells him that it has been years now and people change. Ted also gets a call from his old boss Hammond Druthers (Bryan Cranston) who offers Ted a job in Chicago in light of his success with the GNB headquarters. Hammond on the other hand designed a concave building that raised the temperature at the aquarium to 190 degrees and killed some very rare fish, and also blinded some pilots on their approach to the O'Hare airport. Ted initially refuses, but eventually agrees to think about it under pressure from Druthers. Returning home after the game, Ted finds Robin eating olives which surprises him as she hated olives during their first date, and Robin tells him that she changed her view on them. Reminded of Marshall's words, Ted calls Druthers and turns down the job believing he still has a chance with Robin. Druthers tells Ted that the offer remains open if he changes his mind, and later at MacLaren's, Ted admits he and Robin now only share a "platonish" relationship. However, rather than immediately pursue her, he wants to leave it up to fate to bring them together.
Flashforwarding back to the Farhampton Inn, Barney says that despite all of the challenges, he still hasn't finished one more challenge - to cheer up Robin. Now inspired by what Barney has done, Robin kisses him as Ted watches them sadly, feeling that his decision to leave his relationship with her up to fate may have cost him a future with her.
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