On "Gilmore Girls", which actor played Rory's first boyfriend, Dean Forester?

On "Gilmore Girls," Jared Padalecki played Rory's first boyfriend, Dean Forester. Dean is introduced in the pilot as a new student in Stars Hollow and quickly develops a relationship with Rory Gilmore. His thoughtful but increasingly strained romance with Rory becomes one of the show's earliest major storylines.

Padalecki was cast as Dean in 2000 and played the role through the original series, with the character appearing in recurring and main-cast capacities across different seasons. Dean and Rory's relationship is challenged when Jess Mariano arrives and forms a close connection with Rory. Dean later marries Lindsay Lister, but his continuing feelings for Rory lead to an affair and further complications.

Padalecki is sometimes confused with the actors who played Rory's other major love interests: Milo Ventimiglia played Jess Mariano, while Matt Czuchry played Logan Huntzberger. After "Gilmore Girls," Padalecki became widely known for playing Sam Winchester in "Supernatural." He also returned as Dean in the 2016 revival.