Fiona ponders the morality of getting involved with a high-school crush who’s now married; Frank pulls out all the stops in an effort to stay in the good graces of his meal ticket, Dottie; and Harry’s health issues leave Debbie obsessing over death. Meanwhile, Kevin considers buying the Alibi; Lip takes a meeting with an Army officer to see about getting Ian into West Point; Jody asks for Frank’s permission to marry Karen.