Dean Forester (Jared Padalecki) appears in the first episode of Gilmore Girls, and is immediately set up to be Rory’s boyfriend with a meet cute that involves books and a movie reference. Dean was written to be the perfect first boyfriend for a teenage girl, which seems to mean he has almost no life or personality apart from being in love with Rory, and an obsessive jealous streak. I guess those are things that inexperienced teenage girls might find endearing. However, it didn’t take long for cracks to begin showing in the perfect Dean facade, so perhaps even the writers got bored with this conceit.
Jared Padalecki was not the first choice to play Dean: in the original Pilot episode, he was played by Nathan Wetherington, who gave him a slightly more bashful, skater-boy feel. Interestingly, in a later episode Lorelai says that Dean reminds her of Christopher, Rory’s father, and while Padalecki doesn’t really resemble David Sutcliffe, Wetherington looks much more like him.
Nathan Wetherington was considered for the role of Anakin Skywalker in the Stars Wars prequels, but took himself out of the running when he learned he had the role of Dean on Gilmore Girls, and also missed out on playing Seth on teen drama series The OC, so he’s had some unlucky breaks.