James Van Der Beek Made Several Guest Appearances
Best known for his role as Dawson Leery, in “Dawson’s Creek,” James Van Der Beek appeared several times on “How I Met Your Mother” as Simon Tremblay. His first appearance was in the musical video for the song “Sandcastles in the Sand.” Robin and him dated for the entire Canadian summer, which is a maximum of a week and a half. They broke up because Simon dumped her for another girl who had a pool. After two years, they started dating again, but then he dumped her again for the same girl.