- Marshall's game night leads to some startling and very embarrassing revelations.
- During a game night Robin gets to meet Victoria. What actually was planned to be a funny night turns quite serious when Barney's former love Shannon gives an old tape to Lily which shows the "real" Barney. While watching the tape an embarrassed Barney storms off. When he returns, Barney tells a story from 1998, when he seems to have been a whole different person, and what made him the person he is today. To make Barney feel better, all others also tell their most embarrassing stories.—Sab
- Marshall is seen as the expert gamesman among their group. So it's with glee that he is asked to be head of their games night. He uses the event to unveil his new game, which he's named Marshgammon, a combination of the best of all his favorite games (with one notable exception). This night marks Victoria's first night with the gang, and since Marshall and Lily have vowed to Ted that they won't go all "Mom" on him and question Victoria on her life, Marshall uses Marshgammon for another purpose besides just playing a game. The night proves difficult for Robin as her feelings for Ted strengthen. The one person who the night also unexpectedly is difficult for is Barney, as Lily tells him that she has a videotape for him from an old girlfriend of his named Shannon. Although the gang is ultimately able to watch the video, Barney tells them that the story behind it marks the most embarrassing incident in his life. Before he will tell the entire story, he makes everyone tell their most embarrassing story, Ted's which he knows (which he and Barney call the rereturn) and makes him tell, which Ted doesn't want to especially in front of Robin and Victoria together. But Barney's story truly does reflect the person he is today.—Huggo
- Every time Marshall, Lily, Ted, Robin, and Barney hold a game night together, Marshall always wins no matter what the game is, so the others decide that he should always run game nights. Marshall decides to create his own game, "Marshgammon", which few people understand (although a player must drink if they ask "What?"). Ted plans to bring Victoria along, and tells Marshall, Lily, and Barney not to scare her off, despite the fact that, as pointed out by Barney, Ted hasn't told Victoria that he and Robin dated, nor of the story of the "re-return". All reluctantly promise not to ruin things (Ted has made Lily and Marshall promise not to interrogate Victoria about her past), but Marshall uses the game questions to find out personal information about Victoria (like if she ever cheated in a relationship). Lily mentions a girl named Shannon whom she ran into. Barney denies the existence of this girl, But Lily says she gave her a videotape to give to Barney. Lily gives it to him and he violently destroys it, but Lily reveals that she gave him a tape of Ted's graduation and hid the real one. Over Barney's objections, they watch the tape, and see a long-haired, hippie like Barney, playing a keyboard and singing a weepy, desperate love song to a girl named Shannon. Embarrassed and humiliated, Barney ejects the tape and walks out.
Barney meets all of them at the bar later, stating that that tape was the most embarrassing thing that happened to him. While the others want to know how it happened, Barney goads Marshall to confess an embarrassing moment. Marshall confesses that he was seen half-naked by Lily's kindergarten class after using a shared toilet in the school during which walked in on by another student from a different class. This leads Barney to tell the story that led to the creation of the tape: in 1998, when he was 23, he was a hemp-wearing, peace loving hippie who worked in a coffee shop with his girlfriend Shannon. "Saving themselves" for marriage, they had planned on going to Nicaragua with the Peace Corps, until Shannon failed to meet him on the night they were supposed to leave. He stops at this point, so to encourage him, Lily gets someone else to tell their most embarrassing story as well to take the pressure off of Barney. Marshall spins a game wheel he brought and it lands on Robin. She attempts to tell the story of the time she fell in horse poop on the news - but everyone else has already seen it. However, volunteering in her place, Victoria begins to tell a story involving a game of Truth or Dare, a squeeze bottle of marshmallow ice cream topping, and the hot tub at her grandparent's retirement community, but Future Ted does not recount it, stating that it is "too inappropriate".
Back to Barney's narrative: Shannon revealed to Barney that she backed out, saying that her father did not want her to go, because he has supported her and wants her to stay home. Barney left, but then went back to confront her dad, when she saw Shannon kissing an older man, which he presumed to be her father. To continue into the narrative, Lily tells the story of how Marshall's mother once overheard the couple having sex via a phone call.
Barney then tells that he confronted Shannon and found out that she had begun seeing a yuppie alpha male named Greg, who got her out of her hippie "phase" and bought her stuff. She told him to go and forget about her. Barney postponed his departure instead and made the video and sent it to Shannon, but was humiliated when she and Greg returned and mocked him, and left the coffee shop devastated. Barney then changed his appearance and lifestyle, getting a haircut, wearing suits, and discarding his idealistic world-view.
Finally, he goads Ted to tell his embarrassing story. Although Ted tries to speak of a summer trip to hide it, he relents and tells Victoria that he and Robin had dated at one point - and that on the night he told Robin he loved her he "re-returned" to her apartment to try and kiss her, but was so drunk that he threw up on her doormat and ran away instead. Although that does create some tension between Ted and Victoria, Barney deems it enough to finish his story: after he left Ted and Marshall's apartment with the tape, he visited Shannon, and found out that she has a son. He breaks down in tears, and Lily attempts to comfort him by assuring him that his own life isn't bad compared to Shannon's; Barney looks up, amused by Lily's words, and declares that his life "rocks" because he has money, suits, lots of one-night stands without a "brat" to take care of. He then brags that he finally had sex with Shannon, showing them all the video he took with his cell phone, and leaves, happy with the dirt he has acquired on all of them.
The episode closes with a montage which showcases happier moments coming out of the secrets between Marshall and Lily and Ted and Victoria. Next Barney is seen in the bar appearing jealous of a nearby couple, suggesting his words were really just a front to hide the fact that he might want a meaningful relationship someday, and finally Robin smiling at a new gift-wrapped Scherbatsky doormat. Over that shot, Future Ted hints that he would eventually come to learn of Robin's feelings for him, but that's another story.
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