20Hurt: Lorelai and Jason
Jason couldn't fit in with Stars Hollow or get along with Luke. Lorelai's relationship with the diner owner aside, Jason could never have been a permanent part of her life because of this.
Jason's nickname was Digger; enough said. There were too many marks against Lorelai and Jason's relationship for it to last—or not hurt the series. They kept their relationship a secret from her parents until his father revealed the truth. Jason sued her father for leaving their business partnership. Was
Lorelai really supposed to not side with Richard when she and Jason were never going to last?
Yet, he tried to get her back during the test run for her inn. Really, the only good thing he did was contribute in a small way to Luke and Lorelai getting together.