Played by Jared Padalecki, Dean is Rory's first boyfriend and one of the best characters in Gilmore Girls, but he could have ...

It doesn't take long for the two to become officially a couple. Season 1 has great Rory and Dean Gilmore Girls episodes as Rory finds love with the new kid in town who is working at Doose's Market ...

Cult dramedy. When Rory is upset to discover that Lane and Dean have become study partners, Dean tells Lorelai that he left Rory because she couldn't say 'I love you'.

Padalecki debuted on the first season of Gilmore Girls in 2000 as Dean, the first boyfriend of ... Finn Wolfhard Reveals the 1 Thing He Would Do Differently amid His Breakout Stranger Things ...

7. Kiss and Tell - Cult dramedy.When Rory decides not to tell her mother that she and Dean have kissed, Lorelai takes the liberty of inviting Dean over and Rory is embarrassed by her. More info ...

Gilmore Girls premiered on The WB in 2000 but moved to The CW for its seventh and final season. After the series ended in 2007, a four-part miniseries called Gilmore Girls: A Year in the Life ...