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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. Ted, Lily and Marshall ponder their former personalities that are brought out in the presence of old friends. When Robin is dumped by Simon again, she feels vulnerable and she and Barney end up kissing!