- While out looking for Barney on the day of the wedding, Robin and Ted reminisce about past relationships. Meanwhile, Marshall and Lily finally resolve their issues and Barney befriends two young guys eager to meet women.
- Ted and Robin are out in the middle of the night looking for a missing Barney. Their conversation steers primarily to Ted's past love life, and their respective takes on the good and the bad. In this discussion, Ted also talks about when if any is the right time to let go of the things you love. Barney, meanwhile, is out wandering the streets in a drunken stupor. He comes across two young men named Justin and Kyle who are just coming into their sexual awakening. The threesome become mentor and eventually willing students. And after Lily storms out of the hotel room during her and Marshall's fight after he brings up San Francisco, Marshall continues the argument with several of the ghosts that are haunting that room.—Huggo
- Future Ted tells a story about how he watched his balloon "friend" flying away, stating the event caused him to believe that if you let go of the things you love, you will lose them forever. In the present, on Sunday at 5 AM, 13 hours before the wedding, Ted and Robin are walking along the beach, reminiscing about Ted's top five exes: 5. Stella, 4. Zoey, 3. Slutty Pumpkin, 2. Marshall from the time he and Ted pretended to be a couple to try and sell Barney's apartment, 1. Victoria; and his five worst exes: 5. Blah Blah, 4. "Boats, Boats, Boats", 3. Karen, 2. Zoey (who made both lists), and 1. Jeanette.
Meanwhile, a drunk Barney walks out of the hotel to find two men Justin (Brian McElhaney) & Kyle (Nick Kocher) on the street and takes them to a strip club saying he will teach them how to live. The two men are dismissive of Barney's claims that the way they dress will be key to picking up women when Barney takes them to Tim Gunn to be fitted for suits, but change their minds when they go to a party where Barney plays the "Have you met-" game, setting the boys up with two ladies. At sunrise, Barney tells the boys what he kept telling Ted earlier in the series, that every moment will be legendary if it's shared with friends. Barney hands the two men a stack of napkins; the top napkin says, "The Playbook." Barney leaves after passing on everything he knew about the bachelor life to them.
At the hotel, Marshall imagines a ghost Lily in the hotel room with him. After he brings up San Francisco, the Ghost Lily says he should have this argument with 2006 Lily. When he tells the 2006 Lily that her leaving him was the saddest he's ever felt, she reminds him of his father's death, which brings a shade of his father into the room. Marshall argues with his ghosts until the present imaginary Lily tells him that as long as he thinks of their arguments in terms of winning and losing, he is gradually going to lose her. When the real Lily returns, she and Marshall reconcile and rekindle their romance after she tells him that they should stay in New York.
When Robin asks if Ted has kept in touch with his ex-girlfriends, he says that he has not, though Future Ted reveals that he had lied. In truth, Ted had contacted Stella (Sarah Chalke), Victoria (Ashley Williams), and Jeanette (Abby Elliott) to locate Robin's missing locket. After calling Stella and failing to find the locket in Los Angeles (Stella said that she did not have the time to search her storage locker and so Ted flew all the way to LA to look for it), he learned that Victoria had taken the locket with her to Germany. Victoria agreed to send the locket to Ted, but the package had been intercepted by Jeanette. In the present, Ted confesses to Robin that he and Victoria broke up because he was unwilling to end his friendship with Robin. A stunned Robin tells him that she would have been unhappy, but understanding and that she demands to know why Ted would give up Victoria for their friendship; he admits it is because, for him, there is no top 5 - Robin has always been his top 1. He also says that he is moving to Chicago after the wedding so that it is never awkward between him and her after Robin is married.
It is revealed that Ted's attempt to recover Robin's locket had concluded when Jeanette dropped the locket into the river after, ironically, pointing out how irrational he is for being unwilling to let go of Robin. Ted admits to Jeanette that he loves Robin and wants her to have everything in life that she wants, even if it destroys him in the process. He cannot give up on her. Ted and Robin end their evening watching the sunrise together and Ted finally lets go of Robin, who is shown flying away in his mind, but is still disappointed to learn that Robin thought he should have kissed her at the end of their first date.
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