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Lily and Marshall attempt to raise money to repair their floor by selling off Lily's designer clothing. Lily also discovers an alternative use for her art. We find out it was Abby (Britney Spears) that was Barney's relationship saboteur.
Robin's old boyfriend, Simon (James Van Der Beek), from one of her old pop videos comes to town and they attempt to rekindle their old romance. Barney quests desperately to find the video of her second song which also features Alan Thick and Tiffany.
After everyone joins a gym, Barney sees Rhonda (the woman he lost his virginity to) there. After learning his performance with her was poor, he loses his confidence with women. He attempts to pick up models at a Victoria's Secret Fashion Show.