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Anytime 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; all reluctantly promise not to try to ruin things, but they end up trying their hardest. At game night, Marshall uses the game questions to find out more about Victoria, while Lily reveals that someone gave her a videotape to give to Barney, and once Barney figures out who it is, he panics, destroying a tape of Ted's graduation before Lily revealed that she had hidden the real tape. They watch it, and find a longer-haired, hippie-ish Barney, singing and playing a keyboard while crying. Barney ejects the tape and walks out, and no one can find him.
Barney meets all of them at the bar, and only tells his story once everyone else agrees to tell their embarrassing stories. Marshall confesses that he was seen on the toilet by Lily's kindergarten class, Lily tells the story of how Marshall's mother once overheard the couple having sex via a phone call, Victoria tells 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 that Future Ted states is "too inappropriate" to recount, and Ted confesses 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. Barney then reveals that he once worked in a coffee shop with his girlfriend Shannon. They had planned on going to Nicaragua with the Peace Corps, but Shannon backed out, saying that her father did not want her to go. Barney came back, and found that she had begun seeing a yuppie alpha male named Greg. Barney made the video and sent it to Shannon, but was humiliated by Greg, and left the coffee shop devastated. Barney then changed his appearance and lifestyle, getting a haircut, wearing suits, and discarding his idealistic world-view. He then revealed that after he left Ted and Marshall's apartment, he went over to visit Shannon, and talked with her a bit. He found out that Greg since left her, she now had a son, and that her life had also changed a lot. Then, in typical Barney fashion, he had sex with her, which he captured on video on his cell phone as proof. He also declares that his life "rocks" because he has money, suits, lots of one-night stands and did not have a child to take care of. Barney leaves, and everyone decides that Barney had won game night, since he also has dirt on them now.
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