"Sandcastles in the Sand"  (Season 3 | Episode 16)  22:0
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.
Original Air Date: 4/21/2008