Still trying to get her mind off Steve, Fiona decides to reconnect with Craig, an old high school crush. When she finds an abandoned purse with five hundred dollars in it, she assumes her luck is finally changing. Frank decides to do anything to get Dottie's money, including marrying her and intercepting the page telling her she has a new heart. After Harry, an elderly man who Debbie befriends at the retirement home, dies, Debbie becomes obsessed with death. Kevin thinks about buying the Alibi Room, much to the dismay of Veronica. Lip meets with a soldier to gather information for Ian about West Point. Jody is planning on asking for Karen's hand in marriage.