Fiona hopes her moral compass isn't leading her astray when she reconnects with her married high school crush, but when she finds an abandoned purse with over five hundred dollars inside, she assumes her luck is finally changing; Frank is willing to do just about anything to stay in Dottie's good graces, even marry her; after Harry's passing, Debbie becomes obsessed with death; Kevin thinks about buying the Alibi; Lip meets with a colonel to glean information for Ian about West Point; Jody asks Frank for Karen's hand in marriage.

Frank tries to claim Eddie's insurance benefits and pension, despite being a prime suspect in his death; Fiona attends a ritzy wedding with Richard and lies about her background; Lip is devastated by Karen's rejection; Carl rents Frank's room to a hooker.