First appearing in the Gilmore Girls pilot, Dean Forester (Jared Padalecki) was a key figure in the first part of Rory Gilmore’s (Alexis Bledel) story. However, after season 5, Dean did not appear on the series again, which had a lot to do with Jared Padalecki’s career path outside of the show.
Originally from Chicago, Dean moves to Stars Hollow sometime before the start of the first season with May, Randy, and Clara Forester. After arriving in Stars Hollow, Dean pursues Rory romantically and the two begin dating. However, the relationship soon turns tumultuous, as Rory finds that the relationship is going too fast for her. While they eventually get back together, the arrival of Jess Mariano (Milo Ventimiglia) in Stars Hollow drives them apart again, with Rory becoming more like this new arrival than Dean, who is more working class. Later, Dean begins dating Lindsay Lister (Arielle Kebbel).
As of season 4, Dean appears less in Gilmore Girls, but has one more key plotline, as he eventually proposes to her and marries Lindsay. However, Rory does not react well to the marriage of her ex-boyfriend. At the end of Season 4, Dean cheats on Lindsay with Rory, causing the latter to lose his virginity. This act also drives a temporary wedge between Rory and his mother Lorelai Gilmore (Lauren Graham).
Lindsay soon finds out about the affair and divorces Dean, who begins dating Rory again. However, in Season 5, Episode 8, “Party’s Over”, Dean and Rory break up once and for all when, after a party at Yale, he realizes they no longer work together. In that same season, Dean appears one last time on the Gilmore Girls original series to warn Luke Danes (Scott Patterson) against dating Lorelai.
Although he never dates Rory again and disappears from the series almost entirely after their breakup, Dean appears briefly in Gilmore Girls: A Year in the Life, the 2016 revival of the series. Dean reveals that, since his disappearance, he is married to a woman named Jenny and lives in Scranton, Pennsylvania. They have three sons and are expecting a girl.
In terms of plot, Gilmore Girls had grown beyond Dean as a character, and much of Rory’s growth process involved learning who he would work with and who he wouldn’t. In the end, Dean no longer fit into Rory’s life, and her departure helped her discover more about herself as a person.
Behind the scenes, though, Jared Padalecki was cast as Sam Winchester on The CW’s Supernatural. That said, the actor’s role as Dean on Gilmore Girls nearly cost him that iconic role, as creator Eric Kripke wanted Sam to be a smart character. In the end, however, Padalecki and his manager convinced Kripke that the actor was right for the role, and the rest, as they say, is history.