Name: Lorelai "Rory" Gilmore
Portrayed By: Alexis Bledel
Relation: Ex-Girlfriend
About: Dean met Rory soon after moving to Stars Hollow and they quickly began dating. They were a couple until mid-season three, until they broke up because Rory had developed feelings for Jess Mariano. They agreed to stay friends, although their friendship was rocky at first and always slightly awkward. Despite Rory's strong morals, she started an affair with Dean. Not long after he separated from his wife and they tried their relationship again. However, with Rory going to Yale and making friends in her grandparents crowd, Dean realized they were on different paths and they parted ways permanently.
Name: Jess Mariano
Portrayed By: Milo Ventimiglia
Relation: Rival
About: Dean and Jess became instant enemies after Jess moved to Stars Hollow in season two. Dean tried to make friends, but soon became annoyed with Jess constantly insulting him and the rest of the town. Things only got worse when it became apparent that Jess was interested in Rory--and Rory was interested back. They had many arguments, one even ending in a fist fight that caused property damage. Dean eventually got sick of the way he was being treated and broke up with Rory so she could be with Jess. Unfortunately, Jess continued to antagonize him until he left town.
Name: Lindsay Lister
Portrayed By: Arielle Kebbel
Relation: Ex-Wife
About: Dean compulsively married Lindsay after only dating her for a few months in season four, even though he was clearly still in love with Rory. Their marriage seemed picturesque at first, and Dean tried to make it work but he began growing closer to Rory. Eventually, he and Lindsay began to fight and Dean started an affair with Rory. Feeling guilty, Rory told Dean to try and make his marriage work while she went to Europe with her grandmother. Dean took her advice, but Lindsay ended up finding out about the affair and kicked Dean out, leaving the series forever.