Lucinda Lester

During the conversation Rory has with her grandparents, Richard says he would have married a girl named Lucinda Lester except that he was on the fencing team, which made him enough like Errol Flynn to be attractive to Emily. In a later season, we are told the girl he almost married was named Pennilynn Lott. It is possible he almost married Lucinda and Pennilynn, but doesn’t seem likely.