It Should've Been Lorelai

Christopher returns to town and brings his girlfriend, Sherry, along. Sherry wants to bond with Rory since her and Christopher are becoming serious. Emily finds out about Sherry and tells Lorelai that she has always wanted her and Christopher to end up together. Lorelai tells Christopher that she's always thought that they would get back together, too, and that's why she's never had a relationship that lasted. Christopher gets angry for Lorelai blaming him for her bad relationships, leaving Lorelai hurt while Luke watches.